$80+ Cheap flights from San Francisco Bay Area 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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
May 1 — May 81
Round-trip
1 adult, Economy
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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
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Cheapest flights from San Francisco Bay Area to ChicagoExplore the most affordable flight options available from San Francisco Bay Area to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
Explore the most affordable flight options available from San Francisco Bay Area to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
This Southwest deal was found by Cheapflights users on 3/31. 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 4/2211:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 4/2810:00 am
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 3/31![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 3/31. 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 5/209:05 pm
OAK
- MDW
1 stop5h 55m
Southwest
Wed 5/278:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 3/31![Southwest logo]()
$247
This Frontier deal was found by Cheapflights users on 3/27. 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.
Sat 6/610:15 pm
SFO
- MDW
1 stop10h 57m
Frontier
Mon 6/156:00 am
MDW
- SFO
1 stop15h 25m
Frontier
Deal found 3/27![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 6/18:56 am
SFO
- ORD
1 stop9h 41m
Frontier
Wed 6/109:33 am
ORD
- SFO
2 stops13h 48m
Frontier
Deal found 3/29![Frontier logo]()
$250
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/199:35 pm
SFO
- ORD
1 stop21h 18m
Frontier
Mon 6/296:55 am
ORD
- SFO
1 stop14h 30m
Frontier
Deal found 3/30![Frontier logo]()
$251
This Kissandfly.com deal was found by Cheapflights users on 3/30. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:55 pm
SFO
- MDW
1 stop7h 52m
Frontier
Tue 4/286:10 am
MDW
- SFO
1 stop13h 24m
Frontier
Deal found 3/30![Frontier logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/2710:38 pm
SFO
- ORD
1 stop9h 24m
Multiple Airlines
Sat 6/272:30 pm
ORD
- SFO
1 stop8h 30m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/256:29 pm
SFO
- ORD
1 stop9h 06m
Multiple Airlines
Tue 5/198:00 am
ORD
- SFO
2 stops14h 36m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/109:00 pm
SFO
- ORD
1 stop25h 38m
Multiple Airlines
Mon 4/209:44 pm
ORD
- SFO
2 stops21h 50m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 4/166:29 pm
SFO
- ORD
1 stop9h 21m
Frontier
Tue 4/213:27 pm
ORD
- SFO
2 stops24h 25m
Frontier
Deal found 3/29![Frontier logo]()
$256
This Delta deal was found by Cheapflights users on 3/31. 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.
Wed 5/611:59 pm
SFO
- MDW
1 stop6h 43m
Delta
Wed 5/139:22 am
MDW
- SFO
1 stop6h 53m
Delta
Deal found 3/31![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 3/31. 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 6/25:55 am
SFO
- ORD
1 stop8h 52m
Delta
Tue 6/97:35 am
ORD
- SFO
1 stop7h 56m
Delta
Deal found 3/31![Delta logo]()
$257
Best flights from San Francisco Bay Area to ChicagoDiscover carefully curated flight deals from San Francisco Bay Area to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
Discover carefully curated flight deals from San Francisco Bay Area to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
This United Airlines deal was found by Cheapflights users on 3/29. 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.
Mon 4/2011:52 pm
SFO
- ORD
Nonstop4h 28m
United Airlines
Mon 4/2710:45 pm
ORD
- SFO
Nonstop4h 50m
United Airlines
Deal found 3/29![United Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 3/30. 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.
Mon 4/2710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 4/2910:05 am
MDW
- SJC
1 stop8h 10m
Southwest
Deal found 3/30![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 3/31. 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.
Wed 5/278:05 pm
SJC
- MDW
2 stops10h 37m
Delta
Mon 6/11:59 pm
MDW
- SJC
1 stop8h 39m
Delta
Deal found 3/31![Delta logo]()
$276
This Alaska Airlines deal was found by Cheapflights users on 3/27. 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.
Tue 8/183:15 pm
SJC
- ORD
1 stop6h 24m
Alaska Airlines
Wed 8/269:20 am
ORD
- SJC
1 stop7h 19m
Alaska Airlines
Deal found 3/27![Alaska Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Wed 5/610:40 pm
SFO
- RFD
1 stop11h 20m
Multiple Airlines
Sun 5/1012:50 pm
RFD
- SFO
1 stop21h 40m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 3/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/203:45 pm
SJC
- ORD
1 stop6h 44m
United Airlines
Thu 4/237:46 pm
ORD
- SJC
Nonstop4h 55m
United Airlines
Deal found 3/30![United Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 3/30. 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.
Mon 4/278:30 pm
OAK
- MDW
1 stop6h 05m
Southwest
Thu 4/309:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 3/30![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 3/29. 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.
Thu 4/239:37 am
SJC
- ORD
1 stop6h 27m
Delta
Sat 4/252:09 pm
ORD
- SJC
1 stop9h 12m
Delta
Deal found 3/29![Delta logo]()
$285
This Southwest deal was found by Cheapflights users on 3/29. 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 5/71:25 pm
OAK
- MDW
1 stop7h 15m
Southwest
Tue 5/128:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 3/29![Southwest logo]()
$275
This Alaska Airlines deal was found by Cheapflights users on 3/27. 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 4/222:09 pm
OAK
- ORD
1 stop7h 50m
Alaska Airlines
Tue 4/288:50 am
ORD
- OAK
1 stop7h 48m
Alaska Airlines
Deal found 3/27![Alaska Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 3/27. 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 4/1412:34 pm
OAK
- ORD
1 stop6h 44m
Delta
Mon 4/207:10 pm
ORD
- OAK
1 stop6h 44m
Delta
Deal found 3/27![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 3/30. 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 5/66:00 am
OAK
- MDW
1 stop7h 55m
Southwest
Sat 5/91:00 pm
MDW
- OAK
1 stop7h 45m
Southwest
Deal found 3/30![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 3/29. 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 5/125:05 pm
OAK
- ORD
2 stops15h 11m
Delta
Fri 5/157:45 pm
ORD
- OAK
1 stop6h 12m
Delta
Deal found 3/29![Delta logo]()
$294
This Alaska Airlines deal was found by Cheapflights users on 3/31. 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 5/27:23 am
STS
- ORD
1 stop9h 40m
Alaska Airlines
Tue 5/53:52 pm
ORD
- STS
1 stop21h 06m
Alaska Airlines
Deal found 3/31![Alaska Airlines logo]()
$338
This Southwest deal was found by Cheapflights users on 3/27. 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 4/306:35 am
SJC
- ORD
1 stop10h 15m
Southwest
Mon 5/44:50 pm
ORD
- SJC
1 stop7h 35m
Southwest
Deal found 3/27![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:20 pm
SJC
- ORD
2 stops9h 41m
Delta
Wed 4/297:35 am
ORD
- SJC
2 stops9h 33m
Delta
Deal found 3/30![Delta logo]()
$296
This United Airlines deal was found by Cheapflights users on 3/27. 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 4/1712:45 am
SFO
- ORD
Nonstop4h 22m
United Airlines
Sat 4/259:10 am
ORD
- SFO
Nonstop4h 53m
United Airlines
Deal found 3/27![United Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 3/27. 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 5/118:30 pm
OAK
- MDW
1 stop6h 05m
Southwest
Wed 5/1312:35 pm
MDW
- OAK
2 stops7h 40m
Southwest
Deal found 3/27![Southwest logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Wed 5/2010:40 pm
SFO
- RFD
1 stop11h 41m
Multiple Airlines
Sun 5/241:11 pm
RFD
- SFO
1 stop8h 38m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$427
This Alaska Airlines deal was found by Cheapflights users on 3/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:23 am
STS
- ORD
1 stop9h 40m
Alaska Airlines
Thu 4/303:52 pm
ORD
- STS
1 stop9h 35m
Alaska Airlines
Deal found 3/30![Alaska Airlines logo]()
$358
This United Airlines deal was found by Cheapflights users on 3/27. 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 5/26:30 am
SJC
- ORD
Nonstop4h 27m
United Airlines
Wed 5/63:35 pm
ORD
- SJC
Nonstop4h 56m
United Airlines
Deal found 3/27![United Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 6/610:40 pm
SFO
- RFD
1 stop11h 43m
Multiple Airlines
Sun 6/149:19 am
RFD
- SFO
2 stops25h 27m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$431
This Southwest deal was found by Cheapflights users on 3/28. 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.
Sat 4/1811:45 am
SFO
- ORD
2 stops8h 35m
Southwest
Sat 4/257:00 am
ORD
- SFO
2 stops12h 25m
Southwest
Deal found 3/28![Southwest logo]()
$295
This Alaska Airlines deal was found by Cheapflights users on 3/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:50 am
STS
- ORD
1 stop6h 50m
Alaska Airlines
Fri 4/243:52 pm
ORD
- STS
1 stop9h 35m
Alaska Airlines
Deal found 3/30![Alaska Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 3/31. 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.
Fri 5/111:59 pm
SFO
- MDW
1 stop7h 07m
Delta
Thu 5/77:13 pm
MDW
- SFO
1 stop6h 37m
Delta
Deal found 3/31![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 3/27. 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 4/297:20 am
SFO
- ORD
2 stops9h 30m
Southwest
Sat 5/26:15 am
ORD
- SFO
2 stops13h 10m
Southwest
Deal found 3/27![Southwest logo]()
$295
This United Airlines deal was found by Cheapflights users on 3/27. 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.
Wed 4/226:30 am
SJC
- ORD
Nonstop4h 26m
United Airlines
Sat 4/253:35 pm
ORD
- SJC
Nonstop4h 55m
United Airlines
Deal found 3/27![United Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 5/225:25 pm
SFO
- RFD
2 stops16h 46m
Multiple Airlines
Mon 5/259:13 pm
RFD
- SFO
1 stop21h 17m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$443
This Alaska Airlines deal was found by Cheapflights users on 3/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:23 am
STS
- ORD
1 stop9h 40m
Alaska Airlines
Sat 5/96:00 am
ORD
- STS
1 stop8h 21m
Alaska Airlines
Deal found 3/30![Alaska Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:20 pm
SJC
- ORD
2 stops9h 41m
Delta
Thu 4/237:35 am
ORD
- SJC
2 stops11h 24m
Delta
Deal found 3/30![Delta logo]()
$352
Last-minute flights from San Francisco Bay Area to ChicagoDiscover last-minute flight deals from San Francisco Bay Area to Chicago. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco Bay Area to Chicago. Data last updated April 1, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Thu 4/99:05 pm
SFO
- ORD
1 stop14h 14m
Frontier
Mon 4/139:06 pm
ORD
- SFO
1 stop23h 39m
Frontier
Deal found 3/27![Frontier logo]()
$251
This Cheapflightsfares deal was found by Cheapflights users on 3/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1010:50 pm
SFO
- ORD
1 stop16h 36m
Frontier
Mon 4/139:06 pm
ORD
- SFO
1 stop23h 39m
Frontier
Deal found 3/29![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/109:00 pm
SFO
- ORD
1 stop25h 38m
Multiple Airlines
Mon 4/209:44 pm
ORD
- SFO
2 stops21h 50m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/152:47 pm
SFO
- ORD
2 stops17h 36m
Multiple Airlines
Sat 4/185:50 am
ORD
- SFO
1 stop13h 44m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$256
This Kissandfly.com deal was found by Cheapflights users on 3/30. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:55 pm
SFO
- MDW
1 stop7h 52m
Frontier
Tue 4/286:10 am
MDW
- SFO
1 stop13h 24m
Frontier
Deal found 3/30![Frontier logo]()
$252
This Southwest deal was found by Cheapflights users on 3/31. 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 4/2211:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 4/2810:00 am
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 3/31![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 3/31. 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 4/2210:15 am
OAK
- ORD
1 stop6h 35m
Southwest
Tue 4/284:50 pm
ORD
- OAK
1 stop7h 45m
Southwest
Deal found 3/31![Southwest logo]()
$257
This Priceline deal was found by Cheapflights users on 3/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:16 pm
SFO
- MDW
1 stop11h 14m
Frontier
Mon 4/276:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Deal found 3/27![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/256:29 pm
SFO
- ORD
1 stop9h 06m
Multiple Airlines
Wed 5/138:00 am
ORD
- SFO
2 stops14h 36m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/2710:38 pm
SFO
- ORD
1 stop9h 24m
Multiple Airlines
Sat 6/272:30 pm
ORD
- SFO
1 stop8h 30m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 5/2211:59 pm
SFO
- ORD
1 stop14h 17m
Frontier
Tue 5/266:55 am
ORD
- SFO
1 stop14h 39m
Frontier
Deal found 3/27![Frontier logo]()
$253
This Delta deal was found by Cheapflights users on 3/31. 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.
Wed 5/276:15 am
SFO
- ORD
1 stop6h 42m
Delta
Wed 5/277:45 pm
ORD
- SFO
1 stop6h 42m
Delta
Deal found 3/31![Delta logo]()
$257
One-way flights from San Francisco Bay Area to ChicagoSearch for one-way flight options from San Francisco Bay Area to Chicago. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
Search for one-way flight options from San Francisco Bay Area to Chicago. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Frontier deal was found by Cheapflights users on 3/27. 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 4/206:39 pm
SJC
- ORD
1 stop9h 11m
Frontier
Deal found 3/27![Frontier logo]()
$80
This CheapOair deal was found by Cheapflights users on 3/31. 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.
Mon 5/1112:57 pm
SJC
- ORD
1 stop15h 42m
Frontier
Deal found 3/31![Frontier logo]()
$92
This CheapOair deal was found by Cheapflights users on 3/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:41 pm
SJC
- ORD
1 stop6h 27m
Frontier
Deal found 3/29![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Mon 4/206:39 pm
SJC
- ORD
1 stop26h 48m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$106
This Frontier deal was found by Cheapflights users on 3/27. 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 6/111:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 3/27![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 3/27. 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 6/18:56 am
SFO
- ORD
1 stop9h 41m
Frontier
Deal found 3/27![Frontier logo]()
$111
This CheapOair deal was found by Cheapflights users on 3/27. 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.
Thu 5/1412:57 pm
SJC
- ORD
1 stop15h 42m
Frontier
Deal found 3/27![Frontier logo]()
$111
This Booking.com deal was found by Cheapflights users on 3/27. 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 5/76:00 am
SFO
- ORD
1 stop12h 37m
Frontier
Deal found 3/27![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Wed 4/222:47 pm
SFO
- MDW
2 stops26h 44m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Tue 5/59:26 pm
SFO
- ORD
2 stops21h 11m
Frontier
Deal found 3/28![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/222:47 pm
SFO
- MDW
2 stops26h 44m
Frontier
Deal found 3/27![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Fri 4/2411:16 pm
SFO
- ORD
1 stop12h 51m
Frontier
Deal found 3/30![Frontier logo]()
$114
Find flight deals from San Francisco Bay Area to Chicago
Keep the following information in mind while searching for San Francisco Bay Area to Chicago flight deals. Data was last updated April 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $237 (Southwest) |
One-way from | $80 (Frontier) |
Popular in | November |
Cheapest in | September |
Average price | $325 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Francisco Bay Area 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 April 1, 2026.
Use the filters below to find and compare flights from San Francisco Bay Area to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Mon 4/20
11:52 pm-6:20 am
Nonstop4h 28m
Chicago O'Hare Intl
Mon 4/27
10:45 pm-1:35 am
Nonstop4h 50m
$265
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 4/27
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Wed 4/29
10:05 am-4:15 pm
1 stop8h 10m
$275
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 4/20
3:45 pm-12:29 am
1 stop6h 44m
Chicago O'Hare Intl
Thu 4/23
7:46 pm-10:41 pm
Nonstop4h 55m
$275
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Mon 4/27
8:30 pm-4:35 am
1 stop6h 05m
Chicago Midway
Thu 4/30
9:50 pm-12:25 am
Nonstop4h 35m
$275
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Thu 5/7
1:25 pm-10:40 pm
1 stop7h 15m
Chicago Midway
Tue 5/12
8:50 pm-11:25 pm
Nonstop4h 35m
$275
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 5/27
8:05 pm-8:42 am
2 stops10h 37m
Chicago Midway
Mon 6/1
1:59 pm-8:38 pm
1 stop8h 39m
$276
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 8/18
3:15 pm-11:39 pm
1 stop6h 24m
Chicago O'Hare Intl
Wed 8/26
9:20 am-2:39 pm
1 stop7h 19m
$277
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 4/23
9:37 am-6:04 pm
1 stop6h 27m
Chicago O'Hare Intl
Sat 4/25
2:09 pm-9:21 pm
1 stop9h 12m
$285
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Wed 5/6
6:00 am-3:55 pm
1 stop7h 55m
Chicago Midway
Sat 5/9
1:00 pm-6:45 pm
1 stop7h 45m
$285
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 4/30
6:35 am-6:50 pm
1 stop10h 15m
Chicago O'Hare Intl
Mon 5/4
4:50 pm-10:25 pm
1 stop7h 35m
$290
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from San Francisco Bay Area to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Francisco Bay Area with our price prediction graph.
OAK-MDW
SFO-MDW
SFO-ORD
OAK-ORD
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 Bay Area to Chicago
zzXIH-CHI
OAK-MDW
SFO-MDW
SFO-ORD
OAK-ORD
What is the cheapest month to book a flight from San Francisco Bay Area to Chicago?
Currently, April is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago (average of $115). Flying from San Francisco Bay Area to Chicago in December is currently the most expensive (average of $233). 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 XIH to CHI?
Find hourly flight availability from San Francisco Bay Area 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 April 1, 2026.
It’s optimal to fly from San Francisco Bay Area to Chicago in the afternoon. By choosing this option you can save up to 35% on the cost of your flight, compared to a flight at noon.
What is the cheapest day to fly from San Francisco Bay Area to Chicago?
Use this chart to determine the cheapest time to fly round-trip from San Francisco Bay Area to Chicago. Price data was last updated on March 28, 2026.
Travelers seeking maximum savings on their San Francisco Bay Area 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 Bay Area to Chicago
Explore weekly flight availability from San Francisco Bay Area 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 April 1, 2026.
The most flights from zzXIH to CHI are scheduled on a Wednesday (91 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (55 on average).
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 April 1, 2026.
See what other customers who have flown with Southwest,Alaska Airlines, andUnited Airlines from San Francisco Bay Area to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
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 Bay Area 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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for San Francisco Bay Area to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 April 1, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San Francisco Bay Area to Chicago by cabin class
Find flights from San Francisco Bay Area to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Francisco Bay Area and Chicago flights
Browse other San Francisco Bay Area and Chicago flight options. Last updated on April 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 9 airlines flying from San Francisco Bay Area to Chicago
Discover the top 9 airlines that operate flights from San Francisco Bay Area 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 April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$101 | Average$270 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$108 | Average$230 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$118 | Average$270 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$128 | Average$363 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$133 | Average$437 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$170 | Average$388 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$185 | Average$426 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$197 | Average$387 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$316 | FlexibilityNo cancel fee | On-time62% |