$134+ Cheap flights from San Francisco (SFO) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Jun 2 — Jun 91
Round-trip
1 adult, Economy
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Find cheap flights from San Francisco to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San Francisco to Chicago are usually found in September or August, booked 52 days in advance, depart on a Wednesday or Tuesday and return on a Thursday
Cheap flight deals from San Francisco to Chicago
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Best
Last-minute
One-way
Cheapest flights from San Francisco to ChicagoExplore the most affordable flight options available from San Francisco to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 3, 2026.
Explore the most affordable flight options available from San Francisco to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1811:59 pm
SFO
- ORD
1 stop9h 41m
Frontier
Mon 5/258:46 pm
ORD
- SFO
1 stop26h 18m
Frontier
Deal found 4/29![Frontier logo]()
$279
This Trip.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:10 pm
SFO
- MDW
1 stop10h 59m
Frontier
Thu 6/43:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Deal found 4/30![Frontier logo]()
$280
This Alaska Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:16 am
SFO
- ORD
1 stop10h 34m
Alaska Airlines
Mon 6/17:59 pm
ORD
- SFO
1 stop15h 34m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$280
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Tue 5/193:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Deal found 4/29![Frontier logo]()
$281
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
SFO
- ORD
1 stop12h 32m
Frontier
Wed 5/136:55 am
ORD
- SFO
1 stop14h 39m
Frontier
Deal found 4/29![Frontier logo]()
$281
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Wed 6/39:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 4/29![Southwest logo]()
$282
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:48 pm
SFO
- ORD
Nonstop4h 47m
American Airlines
Wed 6/36:45 am
ORD
- SFO
Nonstop4h 40m
American Airlines
Deal found 4/30![American Airlines logo]()
$282
This Booking.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Wed 5/133:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Deal found 4/28![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/263:43 pm
SFO
- ORD
1 stop11h 45m
Frontier
Thu 7/307:15 am
ORD
- SFO
1 stop11h 17m
Frontier
Deal found 5/1![Frontier logo]()
$283
This Cheapflightsfares deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
SFO
- ORD
1 stop12h 32m
Frontier
Sat 5/1612:05 pm
ORD
- SFO
1 stop12h 59m
Frontier
Deal found 5/1![Frontier logo]()
$284
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:15 pm
SFO
- MDW
1 stop8h 40m
Southwest
Mon 6/15:25 pm
MDW
- SFO
1 stop7h 00m
Southwest
Deal found 4/29![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:59 pm
SFO
- ORD
1 stop6h 46m
Delta
Mon 6/17:45 pm
ORD
- SFO
1 stop6h 27m
Delta
Deal found 4/28![Delta logo]()
$285
Best flights from San Francisco to ChicagoDiscover carefully curated flight deals from San Francisco to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 3, 2026.
Discover carefully curated flight deals from San Francisco to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 3, 2026.
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:34 pm
SFO
- ORD
Nonstop4h 21m
United Airlines
Thu 9/174:20 pm
ORD
- SFO
Nonstop4h 52m
United Airlines
Deal found 4/29![United Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:40 pm
SFO
- MDW
1 stop6h 55m
Southwest
Tue 6/212:50 pm
MDW
- SFO
2 stops10h 35m
Southwest
Deal found 4/28![Southwest logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/310:01 pm
SFO
- RFD
2 stops44h 19m
Multiple Airlines
Wed 6/108:50 pm
RFD
- SFO
1 stop21h 31m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/82:30 pm
SFO
- ORD
1 stop6h 48m
Delta
Wed 6/107:37 pm
ORD
- SFO
1 stop6h 21m
Delta
Deal found 5/1![Delta logo]()
$315
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:34 pm
SFO
- ORD
Nonstop4h 25m
United Airlines
Fri 5/293:26 pm
ORD
- SFO
Nonstop4h 52m
United Airlines
Deal found 4/29![United Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:15 am
SFO
- ORD
1 stop8h 36m
Delta
Mon 6/16:06 pm
ORD
- SFO
1 stop8h 40m
Delta
Deal found 4/28![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:20 am
SFO
- MDW
2 stops8h 15m
Southwest
Sat 5/306:15 am
MDW
- SFO
1 stop7h 25m
Southwest
Deal found 4/30![Southwest logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2911:10 am
SFO
- RFD
1 stop23h 14m
Multiple Airlines
Mon 8/37:50 pm
RFD
- SFO
2 stops26h 03m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:05 am
SFO
- ORD
Nonstop4h 24m
United Airlines
Wed 6/37:30 am
ORD
- SFO
Nonstop4h 49m
United Airlines
Deal found 5/2![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:15 am
SFO
- ORD
1 stop8h 33m
Delta
Sun 8/167:30 am
ORD
- SFO
1 stop7h 00m
Delta
Deal found 4/29![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:45 pm
SFO
- MDW
1 stop8h 25m
Southwest
Tue 8/48:30 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 4/28![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:15 pm
SFO
- MDW
2 stops8h 40m
Southwest
Tue 6/212:50 pm
MDW
- SFO
2 stops10h 35m
Southwest
Deal found 4/28![Southwest logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/127:07 pm
SFO
- RFD
1 stop15h 07m
Multiple Airlines
Mon 6/2910:05 pm
RFD
- SFO
1 stop20h 16m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$383
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:35 pm
SFO
- ORD
Nonstop4h 23m
United Airlines
Tue 6/29:33 pm
ORD
- SFO
Nonstop4h 57m
United Airlines
Deal found 4/28![United Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/712:40 am
SFO
- MDW
1 stop5h 57m
Delta
Fri 6/197:16 pm
MDW
- SFO
1 stop6h 37m
Delta
Deal found 5/2![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Tue 9/88:30 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 5/1![Southwest logo]()
$349
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2512:50 am
SFO
- ORD
Nonstop4h 26m
United Airlines
Mon 6/19:33 pm
ORD
- SFO
Nonstop4h 57m
United Airlines
Deal found 4/28![United Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:11 pm
SFO
- RFD
1 stop23h 12m
Multiple Airlines
Sun 7/191:14 pm
RFD
- SFO
1 stop21h 29m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2710:58 pm
SFO
- RFD
1 stop11h 25m
Multiple Airlines
Mon 6/2910:05 pm
RFD
- SFO
1 stop20h 16m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/111:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Fri 7/319:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 4/29![Southwest logo]()
$362
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:34 pm
SFO
- ORD
Nonstop4h 25m
United Airlines
Tue 6/99:48 pm
ORD
- SFO
Nonstop4h 57m
United Airlines
Deal found 5/1![United Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/610:50 pm
SFO
- RFD
1 stop11h 33m
Multiple Airlines
Fri 6/129:10 pm
RFD
- SFO
2 stops24h 04m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1911:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Tue 6/237:45 am
MDW
- SFO
2 stops10h 00m
Southwest
Deal found 5/2![Southwest logo]()
$364
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:34 pm
SFO
- ORD
Nonstop4h 25m
United Airlines
Sun 6/146:13 am
ORD
- SFO
Nonstop4h 37m
United Airlines
Deal found 5/2![United Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:44 pm
SFO
- RFD
2 stops34h 37m
Multiple Airlines
Mon 6/89:10 pm
RFD
- SFO
1 stop21h 11m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$402
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:00 pm
SFO
- MDW
2 stops8h 35m
Southwest
Wed 7/86:40 pm
MDW
- SFO
1 stop6h 35m
Southwest
Deal found 5/1![Southwest logo]()
$369
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:34 pm
SFO
- ORD
Nonstop4h 25m
United Airlines
Sun 6/76:13 am
ORD
- SFO
Nonstop4h 37m
United Airlines
Deal found 5/3![United Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/711:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Wed 6/106:45 am
MDW
- SFO
1 stop6h 50m
Southwest
Deal found 4/29![Southwest logo]()
$377
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:30 pm
SFO
- ORD
Nonstop4h 27m
United Airlines
Tue 5/269:48 pm
ORD
- SFO
Nonstop4h 57m
United Airlines
Deal found 5/1![United Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:45 pm
SFO
- RFD
1 stop23h 38m
Multiple Airlines
Mon 5/259:13 pm
RFD
- SFO
2 stops23h 06m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$435
Last-minute flights from San Francisco to ChicagoDiscover last-minute flight deals from San Francisco to Chicago. Data last updated May 3, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco to Chicago. Data last updated May 3, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
SFO
- ORD
1 stop12h 32m
Frontier
Wed 5/136:55 am
ORD
- SFO
1 stop14h 39m
Frontier
Deal found 4/29![Frontier logo]()
$281
This Booking.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Wed 5/133:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Deal found 4/28![Frontier logo]()
$283
This Cheapflightsfares deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
SFO
- ORD
1 stop12h 32m
Frontier
Sat 5/1612:05 pm
ORD
- SFO
1 stop12h 59m
Frontier
Deal found 5/1![Frontier logo]()
$284
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Tue 5/193:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Deal found 4/29![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1811:59 pm
SFO
- ORD
1 stop9h 41m
Frontier
Mon 5/258:46 pm
ORD
- SFO
1 stop26h 18m
Frontier
Deal found 4/29![Frontier logo]()
$279
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Wed 5/2712:50 pm
MDW
- SFO
2 stops10h 35m
Southwest
Deal found 4/29![Southwest logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:56 am
SFO
- ORD
1 stop9h 36m
Frontier
Sun 5/319:37 pm
ORD
- SFO
1 stop12h 24m
Frontier
Deal found 4/30![Frontier logo]()
$283
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Wed 6/39:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 4/29![Southwest logo]()
$282
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:48 pm
SFO
- ORD
Nonstop4h 47m
American Airlines
Wed 6/36:45 am
ORD
- SFO
Nonstop4h 40m
American Airlines
Deal found 4/30![American Airlines logo]()
$282
This Alaska Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:16 am
SFO
- ORD
1 stop10h 34m
Alaska Airlines
Mon 6/17:59 pm
ORD
- SFO
1 stop15h 34m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:15 pm
SFO
- MDW
1 stop8h 40m
Southwest
Mon 6/15:25 pm
MDW
- SFO
1 stop7h 00m
Southwest
Deal found 4/28![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:59 pm
SFO
- ORD
1 stop6h 46m
Delta
Mon 6/17:45 pm
ORD
- SFO
1 stop6h 27m
Delta
Deal found 4/28![Delta logo]()
$285
One-way flights from San Francisco to ChicagoSearch for one-way flight options from San Francisco to Chicago. Find affordable one-way fares based on user searches. Data last updated May 3, 2026.
Search for one-way flight options from San Francisco to Chicago. Find affordable one-way fares based on user searches. Data last updated May 3, 2026.
This Trip.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/710:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 5/1![Frontier logo]()
$134
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:55 am
SFO
- ORD
1 stop12h 00m
Southwest
Deal found 5/1![Southwest logo]()
$134
This Super.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1511:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 5/1![Frontier logo]()
$135
This Cheapflightsfares deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:26 pm
SFO
- ORD
1 stop13h 13m
Frontier
Deal found 5/2![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/97:11 pm
SFO
- RFD
1 stop23h 12m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
SFO
- ORD
1 stop12h 32m
Frontier
Deal found 5/1![Frontier logo]()
$136
This Flightnetwork deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
SFO
- ORD
1 stop12h 32m
Frontier
Deal found 5/2![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:58 pm
SFO
- ORD
1 stop28h 30m
Frontier
Deal found 5/1![Frontier logo]()
$138
This Trip.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1811:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 5/1![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:25 pm
SFO
- ORD
2 stops25h 18m
Frontier
Deal found 5/2![Frontier logo]()
$139
This Booking.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:00 am
SFO
- ORD
1 stop12h 32m
Frontier
Deal found 5/1![Frontier logo]()
$141
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:10 pm
SFO
- MDW
1 stop6h 55m
Southwest
Deal found 4/30![Southwest logo]()
$143
Find flight deals from San Francisco to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Francisco (SFO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $279 (Kiwi.com) |
One-way from | $134 (Trip.com) |
Popular in | March |
Cheapest in | September |
Average price | $380 |
Good round-trip deal | $393 or less |
Good one-way deal | $208 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Francisco to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 3, 2026.
Use the filters below to find and compare flights from San Francisco to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Tue 9/15
6:34 pm-12:55 am
Nonstop4h 21m
Chicago O'Hare Intl
Thu 9/17
4:20 pm-7:12 pm
Nonstop4h 52m
$286
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 5/27
7:40 pm-4:35 am
1 stop6h 55m
Chicago Midway
Tue 6/2
12:50 pm-9:25 pm
2 stops10h 35m
$290
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Tue 5/26
6:34 pm-12:59 am
Nonstop4h 25m
Chicago O'Hare Intl
Fri 5/29
3:26 pm-6:18 pm
Nonstop4h 52m
$295
San FranciscoChicago
SFO - RFD
SFORFD
San Francisco
Wed 6/3
10:01 pm-8:20 pm
2 stops44h 19m
Chicago Greater Rockford
Wed 6/10
8:50 pm-4:21 pm
1 stop21h 31m
$303
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Mon 6/8
2:30 pm-11:18 pm
1 stop6h 48m
Chicago O'Hare Intl
Wed 6/10
7:37 pm-11:58 pm
1 stop6h 21m
$315
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Mon 5/25
6:15 am-4:51 pm
1 stop8h 36m
Chicago O'Hare Intl
Mon 6/1
6:06 pm-12:46 am
1 stop8h 40m
$329
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 5/27
6:20 am-4:35 pm
2 stops8h 15m
Chicago Midway
Sat 5/30
6:15 am-11:40 am
1 stop7h 25m
$334
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Tue 6/2
5:05 am-11:29 am
Nonstop4h 24m
Chicago O'Hare Intl
Wed 6/3
7:30 am-10:19 am
Nonstop4h 49m
$337
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Tue 8/11
6:15 am-4:48 pm
1 stop8h 33m
Chicago O'Hare Intl
Sun 8/16
7:30 am-12:30 pm
1 stop7h 00m
$342
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 7/30
6:45 pm-5:10 am
1 stop8h 25m
Chicago Midway
Tue 8/4
8:30 pm-11:05 pm
Nonstop4h 35m
$345
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from San Francisco to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Francisco to Chicago in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Francisco-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Francisco-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Francisco-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Francisco-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Francisco-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from San Francisco to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Francisco with our price prediction graph.
SFO-CHI
SFO-ORD
SFO-MDW
SFO-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Francisco to Chicago
SFO-CHI
SFO-ORD
SFO-MDW
SFO-RFD
How far ahead should I book a flight from San Francisco to Chicago?
The best time to book flights from San Francisco to Chicago is 66 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from San Francisco to Chicago?
Currently, September is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $288). Flying from San Francisco to Chicago in January is currently the most expensive (average of $1,094). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SFO to CHI?
Find hourly flight availability from San Francisco to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 3, 2026.
One of the essential ways to save on airfare from San Francisco to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 29% on airfare.
What is the cheapest day to fly from San Francisco to Chicago?
Use this chart to determine the cheapest time to fly round-trip from San Francisco to Chicago. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their San Francisco to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from San Francisco to Chicago
Explore weekly flight availability from San Francisco to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 3, 2026.
The most flights from SFO to CHI are scheduled on a Friday (94 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (62 on average).
How much does it cost to fly round-trip from San Francisco to Chicago?
What’s the top layover airport for flights from San Francisco to Chicago?
Share of 1-stop round-trip flights from San Francisco to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.
Las Vegas (LAS) – chosen by Cheapflights users on 50% of 1-stop itineraries from San Francisco to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from San Francisco to Chicago?
Average round-trip fare for 1-stop flights from San Francisco to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $153.
What’s the fastest layover option from San Francisco to Chicago?
Shortest average travel time for 1-stop one-way flights from San Francisco to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via San Diego (SAN) have the shortest average one-way travel time for 1-stop routes: 7h 01m.
Which airport typically offers the quickest layover for flights from San Francisco to Chicago?
Average layover duration for 1-stop one-way flights from San Francisco to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via San Diego (SAN) offer the fastest connection on this route, with an average layover time of 0h 57m.
How often are flights from San Francisco to Chicago delayed?
About 10% of weekly flights between San Francisco and Chicago have experienced delays in the past year, with the average delay time being 185 minutes.
What is the most punctual flight time for San Francisco to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on San Francisco to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
The best insider tips for San Francisco to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your San Francisco to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 3, 2026.
Read through reviews of airlines operating flights from San Francisco to Chicago, such as Southwest,Alaska Airlines, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Related info for your journey
Find useful and relevant information for your journey from San Francisco to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 3, 2026.
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Find flights from San Francisco to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Francisco and Chicago flights
Browse other San Francisco and Chicago flight options. Last updated on May 3, 2026.
Other flights from San Francisco
Browse through other flights departing from San Francisco. Flights are based on user searches made on Cheapflights and were last updated on May 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 8 airlines flying from San Francisco to Chicago
Discover the top 8 airlines that operate flights from San Francisco to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$101 | Average$270 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$122 | Average$341 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$127 | Average$252 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$133 | Average$444 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$179 | Average$326 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$185 | Average$351 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$198 | Average$372 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$225 | Average$321 | FlexibilityNo cancel fee | On-time62% |