$134+ Cheap flights from San Francisco (SFO) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/30. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Dec 7 — Dec 141
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 February or January, booked 65 days in advance, depart on a Wednesday or Thursday and return on a Thursday
Cheap flight deals from San Francisco to Chicago
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Best
Last-minute
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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 November 7, 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 November 7, 2026.
This Booking.com deal was found by Cheapflights users on 11/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:30 pm -
2 stops12h 56m
Wed 12/212:28 pm -
2 stops23h 12m
Deal found 11/2![Frontier logo]()
$305
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/910:34 am -
1 stop12h 20m
Sat 12/195:59 pm -
2 stops15h 40m
Deal found 11/2![Frontier logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Tue 11/243:29 pm -
1 stop11h 41m
Wed 11/2510:00 pm -
2 stops28h 43m
Deal found 11/2![Frontier logo]()
$306
This Southwest deal was found by Cheapflights users on 11/2. 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.
Wed 12/210:55 am -
1 stop6h 40m
Fri 12/49:55 am -
Nonstop4h 50m
Deal found 11/2![Southwest logo]()
$307
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/263:41 pm -
2 stops14h 05m
Tue 12/16:21 am -
2 stops16h 19m
Deal found 11/2![Frontier logo]()
$307
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:15 am -
2 stops21h 34m
Thu 12/247:00 am -
2 stops16h 26m
Deal found 11/2![Frontier logo]()
$309
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/99:56 pm -
2 stops19h 52m
Sun 12/1310:29 pm -
2 stops13h 10m
Deal found 11/2![Frontier logo]()
$310
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/239:23 pm -
1 stop25h 03m
Sat 1/27:35 am -
1 stop26h 04m
Deal found 11/3![Frontier logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/209:20 pm -
1 stop6h 54m
Wed 12/27:00 am -
2 stops15h 13m
Deal found 11/2![Frontier logo]()
$312
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/128:40 am -
2 stops13h 19m
Mon 12/217:58 pm -
1 stop14h 54m
Deal found 11/3![Alaska Airlines logo]()
$315
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:35 pm -
2 stops20h 09m
Sun 12/64:08 pm -
2 stops19h 31m
Deal found 11/2![Frontier logo]()
$316
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:45 pm -
1 stop6h 40m
Wed 12/26:05 am -
1 stop7h 05m
Deal found 11/3![Southwest logo]()
$317
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 November 7, 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 November 7, 2026.
This Southwest deal was found by Cheapflights users on 11/2. 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.
Mon 11/238:45 pm -
1 stop7h 10m
Wed 12/29:55 am -
Nonstop4h 50m
Deal found 11/2![Southwest logo]()
$333
This Alaska Airlines deal was found by Cheapflights users on 11/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1612:39 pm -
1 stop9h 20m
Mon 1/112:11 pm -
1 stop20h 55m
Deal found 11/2![Alaska Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 11/5. 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 3/21:50 pm -
Nonstop4h 27m
Thu 3/116:00 am -
Nonstop4h 57m
Deal found 11/5![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/2511:59 pm -
1 stop6h 59m
Sun 1/3112:44 pm -
1 stop6h 54m
Deal found 11/3![Delta logo]()
$379
This Southwest deal was found by Cheapflights users on 11/2. 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.
Thu 1/146:20 am -
Nonstop4h 05m
Sun 1/177:50 pm -
Nonstop4h 50m
Deal found 11/2![Southwest logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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.
Sun 1/1010:04 am -
1 stop11h 55m
Tue 1/128:00 am -
2 stops13h 33m
Deal found 11/4![Alaska Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 11/2. 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 12/185:25 am -
2 stops8h 15m
Mon 12/2110:25 pm -
Nonstop4h 55m
Deal found 11/2![Southwest logo]()
$365
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 3/103:05 pm -
1 stop20h 49m
Wed 3/172:54 pm -
1 stop8h 56m
Deal found 11/6![Alaska Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 1/2810:40 pm -
Nonstop4h 23m
Mon 2/12:33 pm -
Nonstop5h 00m
Deal found 11/3![United Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 11/6. 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.
Mon 12/71:05 pm -
1 stop6h 55m
Thu 12/101:20 pm -
2 stops10h 55m
Deal found 11/6![Southwest logo]()
$374
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 1/284:52 pm -
Nonstop4h 23m
Tue 2/24:05 pm -
Nonstop5h 00m
Deal found 11/3![United Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:00 am -
1 stop6h 55m
Mon 11/306:23 pm -
1 stop16h 41m
Deal found 11/3![Delta logo]()
$460
This United Airlines deal was found by Cheapflights users on 11/4. 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 12/175:00 am -
Nonstop4h 28m
Mon 1/114:05 pm -
Nonstop5h 00m
Deal found 11/4![United Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:50 am -
1 stop5h 57m
Mon 11/306:23 pm -
1 stop16h 41m
Deal found 11/3![Delta logo]()
$460
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/155:20 am -
2 stops10h 10m
Sun 1/173:50 pm -
1 stop7h 10m
Deal found 11/3![Southwest logo]()
$384
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/123:05 pm -
1 stop20h 49m
Mon 3/152:54 pm -
2 stops11h 05m
Deal found 11/3![Alaska Airlines logo]()
$443
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 12/196:53 pm -
Nonstop4h 23m
Wed 12/306:00 am -
Nonstop5h 01m
Deal found 11/2![United Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 11/6. 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 12/311:35 pm -
Nonstop4h 25m
Mon 12/76:05 am -
1 stop7h 05m
Deal found 11/6![Southwest logo]()
$405
This Southwest deal was found by Cheapflights users on 11/6. 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 12/26:10 am -
2 stops8h 55m
Sun 12/612:20 pm -
2 stops8h 05m
Deal found 11/6![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 11/6. 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 12/182:15 pm -
1 stop7h 10m
Fri 1/110:10 am -
1 stop8h 05m
Deal found 11/6![Southwest logo]()
$438
Last-minute flights from San Francisco to ChicagoDiscover last-minute flight deals from San Francisco to Chicago. Data last updated November 7, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco to Chicago. Data last updated November 7, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:45 pm -
1 stop6h 40m
Wed 12/26:05 am -
1 stop7h 05m
Deal found 11/3![Southwest logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Tue 11/243:29 pm -
1 stop11h 41m
Wed 11/2510:00 pm -
2 stops28h 43m
Deal found 11/2![Frontier logo]()
$306
This Booking.com deal was found by Cheapflights users on 11/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:30 pm -
2 stops12h 56m
Wed 12/212:28 pm -
2 stops23h 12m
Deal found 11/2![Frontier logo]()
$305
This Southwest deal was found by Cheapflights users on 11/2. 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.
Wed 12/26:00 am -
Nonstop4h 15m
Wed 12/96:00 am -
1 stop9h 50m
Deal found 11/2![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 11/2. 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.
Wed 12/26:10 am -
2 stops8h 55m
Fri 12/49:05 pm -
Nonstop4h 50m
Deal found 11/2![Southwest logo]()
$312
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:35 pm -
2 stops20h 09m
Sun 12/64:08 pm -
2 stops19h 31m
Deal found 11/2![Frontier logo]()
$316
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/99:56 pm -
2 stops19h 52m
Sun 12/1310:29 pm -
2 stops13h 10m
Deal found 11/2![Frontier logo]()
$310
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/128:40 am -
2 stops13h 19m
Mon 12/217:58 pm -
1 stop14h 54m
Deal found 11/3![Alaska Airlines logo]()
$315
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/187:59 am -
2 stops14h 27m
Fri 12/255:40 am -
2 stops13h 04m
Deal found 11/2![Frontier logo]()
$318
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:15 am -
2 stops21h 34m
Thu 12/247:00 am -
2 stops16h 26m
Deal found 11/2![Frontier logo]()
$309
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/239:23 pm -
1 stop25h 03m
Sat 1/27:35 am -
1 stop26h 04m
Deal found 11/3![Frontier logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/2310:21 pm -
1 stop6h 33m
Fri 1/17:35 am -
2 stops26h 04m
Deal found 11/2![Frontier logo]()
$317
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 November 7, 2026.
Search for one-way flight options from San Francisco to Chicago. Find affordable one-way fares based on user searches. Data last updated November 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/309:20 pm -
2 stops25h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$134
This Trip.com deal was found by Cheapflights users on 11/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/224:11 pm -
1 stop11h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:34 am -
1 stop12h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/2410:21 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$137
This CheapOair deal was found by Cheapflights users on 11/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/911:58 pm -
1 stop14h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$138
This Super.com deal was found by Cheapflights users on 11/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:15 am -
1 stop16h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$138
This Super.com deal was found by Cheapflights users on 11/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:15 am -
1 stop16h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$139
This Trip.com deal was found by Cheapflights users on 11/4. 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.
Wed 1/1311:55 pm -
1 stop14h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/102:17 pm -
2 stops12h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 11/6. 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.
Tue 1/511:58 pm -
1 stop14h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/142:17 pm -
2 stops41h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/139:56 pm -
2 stops24h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier 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 November 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $303 (Southwest) |
One-way from | $134 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $451 |
Good round-trip deal | $396 or less |
Good one-way deal | $196 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 7,457,451 searches. Data last updated November 7, 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
Quickest round-trip
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Fri 1/22
11:55 pm-6:05 am
Nonstop4h 10m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$149
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Mon 11/23
6:35 am-12:59 pm
Nonstop4h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$149
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Tue 12/1
11:35 pm-6:00 am
Nonstop4h 25m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$149
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Tue 11/24
12:55 am-7:13 am
Nonstop4h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$149
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Tue 12/22
11:30 pm-5:56 am
Nonstop4h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$156
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Mon 12/21
11:30 pm-5:56 am
Nonstop4h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$156
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Fri 1/1
6:20 am-5:24 pm
1 stop9h 04m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Thu 1/14
11:59 pm-8:58 am
1 stop6h 59m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Tue 11/24
6:00 am-4:39 pm
1 stop8h 39m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Sat 12/12
11:20 am-10:50 pm
1 stop9h 30m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
Showing 1-10 of 43 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | 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-MDW
SFO-ORD
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-MDW
SFO-ORD
What is the cheapest month to book a flight from San Francisco to Chicago?
Currently, January is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $369). Flying from San Francisco to Chicago in June is currently the most expensive (average of $484). 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 November 7, 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 evening could potentially save you up to 11% on airfare.
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 November 7, 2026.
The most flights from SFO to CHI are scheduled on a Wednesday (92 on average). You will have fewer flight options on Saturday, 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?
Airfare is below average for this route at the moment.
San Francisco to Chicago flights typically cost between $352 and $602 in February.The cheapest round-trip price found within the last 5 days was $303 on Southwest (Feb 4-Feb 8).
How often are flights from San Francisco to Chicago delayed?
About 9% 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 Monday 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 9% of flights being delayed.
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 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 October 31, 2026.
Travelers seeking maximum savings on their San Francisco to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 November 7, 2026.
Read through reviews of airlines operating flights from San Francisco to Chicago, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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San Francisco and Chicago flights
Browse other San Francisco and Chicago flight options. Last updated on November 7, 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 November 7, 2026.
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Top 7 airlines flying from San Francisco to Chicago
Discover the top 7 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 7,457,451 searches. Data last updated November 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$122 | Average$376 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$157 | Average$300 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$224 | Average$306 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$401 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$237 | Average$421 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$261 | Average$497 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$437 | FlexibilityNo cancel fee | On-time63% |