$104+ Cheap flights from Chicago (CHI) to San Francisco Bay Area
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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Apr 29 — May 61
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to San Francisco Bay Area 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
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Cheapest flights from Chicago to San Francisco Bay AreaExplore the most affordable flight options available from Chicago to San Francisco Bay Area. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 30, 2026.
Explore the most affordable flight options available from Chicago to San Francisco Bay Area. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 30, 2026.
This Southwest deal was found by Cheapflights users on 3/26. 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 4/218:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Tue 4/2811:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/26![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 3/26. 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 4/144:30 pm
MDW
- OAK
1 stop6h 15m
Southwest
Tue 4/2111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/26![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 3/26. 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 5/63:55 pm
MDW
- OAK
1 stop6h 25m
Southwest
Sat 6/67:55 pm
OAK
- MDW
1 stop7h 25m
Southwest
Deal found 3/26![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 3/26. 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 4/217:45 am
ORD
- OAK
1 stop7h 45m
Southwest
Tue 4/283:00 pm
OAK
- ORD
1 stop6h 55m
Southwest
Deal found 3/26![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 3/26. 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 5/66:15 am
ORD
- OAK
1 stop8h 15m
Southwest
Tue 5/126:00 am
OAK
- ORD
1 stop10h 50m
Southwest
Deal found 3/26![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 3/26. 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 4/219:27 am
MDW
- SFO
1 stop7h 28m
Delta
Wed 4/2210:55 pm
SFO
- MDW
1 stop7h 52m
Delta
Deal found 3/26![Delta logo]()
$237
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 4/154:03 pm
ORD
- SFO
2 stops18h 20m
Multiple Airlines
Wed 4/227:40 pm
SFO
- ORD
1 stop8h 28m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 3/26. 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 4/156:00 am
MDW
- OAK
2 stops12h 24m
Delta
Sat 4/185:55 am
OAK
- MDW
2 stops10h 41m
Delta
Deal found 3/26![Delta logo]()
$237
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Mon 5/410:38 pm
SFO
- MDW
1 stop10h 34m
Frontier
Deal found 3/28![Frontier logo]()
$238
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.
Sat 4/184:10 pm
ORD
- SFO
1 stop8h 42m
Multiple Airlines
Sat 4/257:15 am
SFO
- ORD
1 stop9h 48m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$238
This Southwest deal was found by Cheapflights users on 3/26. 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 4/157:45 am
ORD
- OAK
1 stop12h 20m
Southwest
Sat 4/189:55 am
OAK
- ORD
2 stops10h 25m
Southwest
Deal found 3/26![Southwest logo]()
$238
This Cheapflightsfares deal was found by Cheapflights users on 3/26. 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 6/189:07 pm
ORD
- SFO
1 stop25h 53m
Frontier
Sat 6/208:30 pm
SFO
- ORD
1 stop7h 49m
Frontier
Deal found 3/26![Frontier logo]()
$239
Best flights from Chicago to San Francisco Bay AreaDiscover carefully curated flight deals from Chicago to San Francisco Bay Area that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 30, 2026.
Discover carefully curated flight deals from Chicago to San Francisco Bay Area that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 30, 2026.
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 4/239:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Sat 4/2510:45 am
OAK
- MDW
1 stop6h 35m
Southwest
Deal found 3/27![Southwest logo]()
$217
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:50 am
ORD
- SJC
2 stops10h 09m
Delta
Tue 5/127:10 am
SJC
- ORD
1 stop9h 31m
Delta
Deal found 3/28![Delta logo]()
$290
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.
Fri 5/16:20 am
ORD
- SFO
Nonstop4h 51m
United Airlines
Sat 5/211:56 pm
SFO
- ORD
Nonstop4h 24m
United Airlines
Deal found 3/29![United Airlines logo]()
$309
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/214:10 pm
ORD
- STS
1 stop9h 03m
Alaska Airlines
Tue 4/287:23 am
STS
- ORD
1 stop9h 40m
Alaska Airlines
Deal found 3/28![Alaska Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 3/26. 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 5/63:55 pm
MDW
- OAK
1 stop6h 25m
Southwest
Sat 6/67:55 pm
OAK
- MDW
1 stop7h 25m
Southwest
Deal found 3/26![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 3/26. 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 4/144:30 pm
MDW
- OAK
1 stop6h 15m
Southwest
Tue 4/219:05 pm
OAK
- MDW
1 stop5h 55m
Southwest
Deal found 3/26![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 3/25. 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 5/274:50 pm
ORD
- OAK
1 stop7h 45m
Southwest
Mon 6/112:10 pm
OAK
- ORD
2 stops8h 45m
Southwest
Deal found 3/25![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 3/25. 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 5/77:20 pm
ORD
- OAK
1 stop6h 45m
Southwest
Mon 5/115:20 am
OAK
- ORD
2 stops8h 10m
Southwest
Deal found 3/25![Southwest logo]()
$232
This United Airlines deal was found by Cheapflights users on 3/25. 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 5/266:10 am
ORD
- SFO
Nonstop4h 37m
United Airlines
Sat 5/305:05 am
SFO
- ORD
Nonstop4h 26m
United Airlines
Deal found 3/25![United Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 3/26. 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 4/157:45 am
ORD
- OAK
1 stop12h 20m
Southwest
Sat 4/185:00 am
OAK
- ORD
1 stop7h 30m
Southwest
Deal found 3/26![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 3/25. 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.
Sat 5/99:23 am
MDW
- SJC
2 stops9h 39m
Delta
Sat 5/165:50 am
SJC
- MDW
2 stops10h 43m
Delta
Deal found 3/25![Delta logo]()
$343
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
ORD
- STS
1 stop8h 21m
Alaska Airlines
Sat 5/910:01 am
STS
- ORD
1 stop7h 02m
Alaska Airlines
Deal found 3/28![Alaska Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 3/25. 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 4/246:10 pm
MDW
- OAK
1 stop6h 35m
Southwest
Mon 4/2711:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/25![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 3/26. 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 6/185:57 pm
ORD
- SFO
1 stop7h 56m
Delta
Wed 6/246:00 am
SFO
- ORD
1 stop9h 02m
Delta
Deal found 3/26![Delta logo]()
$355
This Alaska Airlines deal was found by Cheapflights users on 3/26. 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 6/186:22 am
ORD
- OAK
1 stop9h 48m
Alaska Airlines
Wed 6/242:50 pm
OAK
- ORD
1 stop6h 49m
Alaska Airlines
Deal found 3/26![Alaska Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 3/25. 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 5/293:26 pm
ORD
- SFO
Nonstop4h 52m
United Airlines
Sun 5/316:34 pm
SFO
- ORD
Nonstop4h 25m
United Airlines
Deal found 3/25![United Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 3/26. 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 4/67:10 pm
ORD
- OAK
1 stop6h 36m
Delta
Sat 4/115:55 am
OAK
- ORD
1 stop7h 23m
Delta
Deal found 3/26![Delta logo]()
$359
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 4/2010:45 pm
ORD
- SFO
Nonstop4h 50m
United Airlines
Mon 4/277:00 pm
SFO
- ORD
Nonstop4h 28m
United Airlines
Deal found 3/29![United Airlines logo]()
$364
This Alaska Airlines deal was found by Cheapflights users on 3/26. 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 4/303:52 pm
ORD
- STS
1 stop9h 35m
Alaska Airlines
Sat 5/28:20 am
STS
- ORD
2 stops20h 20m
Alaska Airlines
Deal found 3/26![Alaska Airlines logo]()
$368
This Southwest deal was found by Cheapflights users on 3/26. 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 4/305:30 am
MDW
- SFO
2 stops9h 05m
Southwest
Tue 5/52:50 pm
SFO
- MDW
1 stop6h 30m
Southwest
Deal found 3/26![Southwest logo]()
$261
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 6/49:23 am
MDW
- SJC
2 stops9h 39m
Delta
Sun 6/78:15 pm
SJC
- MDW
2 stops10h 22m
Delta
Deal found 3/29![Delta logo]()
$366
This Alaska Airlines deal was found by Cheapflights users on 3/25. 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 4/237:59 pm
ORD
- STS
1 stop16h 59m
Alaska Airlines
Mon 4/278:00 pm
STS
- ORD
1 stop15h 13m
Alaska Airlines
Deal found 3/25![Alaska Airlines logo]()
$379
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.
Tue 4/288:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Tue 5/55:50 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/29![Southwest logo]()
$265
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.
Thu 5/77:50 pm
ORD
- SJC
Nonstop4h 56m
United Airlines
Sun 5/102:46 pm
SJC
- ORD
1 stop6h 12m
United Airlines
Deal found 3/27![United Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 3/26. 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 6/206:22 am
ORD
- OAK
1 stop9h 48m
Alaska Airlines
Mon 6/292:50 pm
OAK
- ORD
1 stop6h 49m
Alaska Airlines
Deal found 3/26![Alaska Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 3/26. 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 6/137:40 am
ORD
- SFO
Nonstop4h 49m
United Airlines
Wed 7/16:34 pm
SFO
- ORD
Nonstop4h 25m
United Airlines
Deal found 3/26![United Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 3/25. 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 5/19:48 am
ORD
- SJC
2 stops11h 19m
Delta
Sun 5/36:00 pm
SJC
- ORD
2 stops12h 01m
Delta
Deal found 3/25![Delta logo]()
$418
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.
Mon 4/274:10 pm
MDW
- SFO
2 stops8h 00m
Southwest
Mon 5/49:15 pm
SFO
- MDW
1 stop8h 20m
Southwest
Deal found 3/28![Southwest logo]()
$290
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.
Mon 4/276:15 pm
ORD
- SFO
1 stop6h 50m
Southwest
Mon 5/41:25 pm
SFO
- ORD
2 stops8h 30m
Southwest
Deal found 3/28![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 3/26. 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 5/207:45 am
ORD
- SJC
1 stop7h 03m
Delta
Wed 5/208:50 pm
SJC
- ORD
2 stops9h 46m
Delta
Deal found 3/26![Delta logo]()
$431
Last-minute flights from Chicago to San Francisco Bay AreaDiscover last-minute flight deals from Chicago to San Francisco Bay Area. Data last updated March 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Francisco Bay Area. Data last updated March 30, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/26. 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 4/144:30 pm
MDW
- OAK
1 stop6h 15m
Southwest
Tue 4/2111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/26![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 3/26. 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 4/157:45 am
ORD
- OAK
1 stop12h 20m
Southwest
Sat 4/185:00 am
OAK
- ORD
1 stop7h 30m
Southwest
Deal found 3/26![Southwest logo]()
$232
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 4/154:03 pm
ORD
- SFO
2 stops18h 20m
Multiple Airlines
Wed 4/227:40 pm
SFO
- ORD
1 stop8h 28m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 3/26. 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 4/157:10 am
ORD
- OAK
2 stops11h 14m
Delta
Sat 4/185:55 am
OAK
- ORD
2 stops11h 57m
Delta
Deal found 3/26![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 3/26. 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 4/156:00 am
MDW
- OAK
2 stops12h 24m
Delta
Sat 4/185:55 am
OAK
- MDW
2 stops10h 41m
Delta
Deal found 3/26![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 3/25. 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 4/169:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Sat 4/2511:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/25![Southwest logo]()
$207
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.
Sat 4/184:10 pm
ORD
- SFO
1 stop8h 42m
Multiple Airlines
Sat 4/257:15 am
SFO
- ORD
1 stop9h 48m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$238
This Southwest deal was found by Cheapflights users on 3/26. 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 4/213:55 pm
MDW
- OAK
1 stop6h 25m
Southwest
Tue 4/2811:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/26![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 3/26. 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 4/217:45 am
ORD
- OAK
1 stop7h 45m
Southwest
Tue 4/283:00 pm
OAK
- ORD
1 stop6h 55m
Southwest
Deal found 3/26![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 3/26. 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 4/219:27 am
MDW
- SFO
1 stop7h 28m
Delta
Wed 4/2210:55 pm
SFO
- MDW
1 stop7h 52m
Delta
Deal found 3/26![Delta logo]()
$237
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.
Wed 4/228:58 pm
ORD
- SFO
1 stop13h 25m
Frontier
Thu 4/236:29 pm
SFO
- ORD
1 stop9h 51m
Frontier
Deal found 3/27![Frontier logo]()
$239
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Mon 5/410:38 pm
SFO
- MDW
1 stop10h 34m
Frontier
Deal found 3/28![Frontier logo]()
$238
One-way flights from Chicago to San Francisco Bay AreaSearch for one-way flight options from Chicago to San Francisco Bay Area. Find affordable one-way fares based on user searches. Data last updated March 30, 2026.
Search for one-way flight options from Chicago to San Francisco Bay Area. Find affordable one-way fares based on user searches. Data last updated March 30, 2026.
This Southwest deal was found by Cheapflights users on 3/26. 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 4/239:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 3/26![Southwest logo]()
$104
This Southwest deal was found by Cheapflights users on 3/25. 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 4/158:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 3/25![Southwest logo]()
$107
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 6/14:50 pm
ORD
- OAK
1 stop9h 05m
Southwest
Deal found 3/27![Southwest logo]()
$114
This Southwest deal was found by Cheapflights users on 3/25. 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 4/1510:30 am
ORD
- OAK
1 stop10h 20m
Southwest
Deal found 3/25![Southwest logo]()
$119
This Southwest deal was found by Cheapflights users on 3/26. 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 4/249:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 3/26![Southwest logo]()
$119
This Delta deal was found by Cheapflights users on 3/26. 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 5/285:19 pm
ORD
- OAK
2 stops8h 38m
Delta
Deal found 3/26![Delta logo]()
$124
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:40 am
MDW
- SFO
1 stop14h 34m
Frontier
Deal found 3/28![Frontier logo]()
$129
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/48:00 am
ORD
- SFO
1 stop25h 53m
Frontier
Deal found 3/27![Frontier logo]()
$129
This CheapOair deal was found by Cheapflights users on 3/26. 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 5/73:52 pm
ORD
- OAK
1 stop8h 31m
Alaska Airlines
Deal found 3/26![Alaska Airlines logo]()
$129
This Super.com deal was found by Cheapflights users on 3/26. 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 4/106:00 am
MDW
- SFO
1 stop15h 19m
Frontier
Deal found 3/26![Frontier logo]()
$130
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:06 pm
ORD
- SFO
1 stop23h 39m
Frontier
Deal found 3/27![Frontier logo]()
$130
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 4/276:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Deal found 3/27![Frontier logo]()
$131
Find flight deals from Chicago to San Francisco Bay Area
Keep the following information in mind while searching for Chicago to San Francisco Bay Area flight deals. Data was last updated March 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $207 (Southwest) |
One-way from | $104 (Southwest) |
Popular in | February |
Cheapest in | May |
Average price | $397 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to San Francisco Bay Area 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 March 30, 2026.
Use the filters below to find and compare flights from Chicago to San Francisco Bay Area that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Thu 4/23
9:50 pm-12:25 am
Nonstop4h 35m
Oakland
Sat 4/25
10:45 am-7:20 pm
1 stop6h 35m
$217
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Wed 5/6
3:55 pm-8:20 pm
1 stop6h 25m
Oakland
Sat 6/6
7:55 pm-5:20 am
1 stop7h 25m
$222
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 4/14
4:30 pm-8:45 pm
1 stop6h 15m
Oakland
Tue 4/21
9:05 pm-5:00 am
1 stop5h 55m
$227
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 5/27
4:50 pm-10:35 pm
1 stop7h 45m
Oakland
Mon 6/1
12:10 pm-10:55 pm
2 stops8h 45m
$232
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Thu 5/7
7:20 pm-12:05 am
1 stop6h 45m
Oakland
Mon 5/11
5:20 am-3:30 pm
2 stops8h 10m
$232
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 4/15
7:45 am-6:05 pm
1 stop12h 20m
Oakland
Sat 4/18
5:00 am-2:30 pm
1 stop7h 30m
$232
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Fri 4/24
6:10 pm-10:45 pm
1 stop6h 35m
Oakland
Mon 4/27
11:55 pm-6:00 am
Nonstop4h 05m
$232
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 4/30
5:30 am-12:35 pm
2 stops9h 05m
San Francisco
Tue 5/5
2:50 pm-11:20 pm
1 stop6h 30m
$261
Quickest round-trip
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 4/28
8:50 pm-11:25 pm
Nonstop4h 35m
Oakland
Tue 5/5
5:50 am-11:55 am
Nonstop4h 05m
$265
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Sat 5/2
8:50 am-4:59 pm
2 stops10h 09m
San Jose
Tue 5/12
7:10 am-6:41 pm
1 stop9h 31m
$290
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to San Francisco Bay Area
Have a flexible travel schedule? Discover the best time to fly to San Francisco Bay Area from Chicago with our price prediction graph.
MDW-OAK
ORD-OAK
MDW-SFO
ORD-SFO
MDW-SJC
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 Chicago to San Francisco Bay Area
CHI-zzXIH
MDW-OAK
ORD-OAK
MDW-SFO
ORD-SFO
What is the cheapest month to book a flight from Chicago to San Francisco Bay Area?
Currently, October is the cheapest month in which you can book a flight from Chicago to San Francisco Bay Area (average of $80). Flying from Chicago to San Francisco Bay Area in February is currently the most expensive (average of $217). 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 CHI to XIH?
Find hourly flight availability from Chicago to San Francisco Bay Area. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 30, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to San Francisco Bay Area in the evening. If you’re flexible enough to do this you can expect to save up to 15% on your trip compared to booking a flight in the morning.
What is the cheapest day to fly from Chicago to San Francisco Bay Area?
Use this chart to determine the cheapest time to fly round-trip from Chicago to San Francisco Bay Area. Price data was last updated on March 28, 2026.
Travelers seeking maximum savings on their Chicago to San Francisco Bay Area flight should consider departing on Tuesday afternoons 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.
Weekly flight availability from Chicago to San Francisco Bay Area
Explore weekly flight availability from Chicago to San Francisco Bay Area. 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 March 30, 2026.
The most flights from CHI to zzXIH are scheduled on a Monday (84 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (46 on average).
Reviews of airlines servicing San Francisco Bay Area
Get insights into the airlines that provide service to San Francisco Bay Area. 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 San Francisco Bay Area. Reviews last updated March 30, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andUnited Airlines from Chicago to San Francisco Bay Area. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to San Francisco Bay Area. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to San Francisco Bay Area
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to San Francisco Bay Area by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to San Francisco Bay Area by cabin class
Find flights from Chicago to San Francisco Bay Area, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and San Francisco Bay Area flights
Browse other Chicago and San Francisco Bay Area flight options. Last updated on March 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to San Francisco Bay Area flights
Consider these flights traveling from Chicago to San Francisco Bay Area.
Top 9 airlines flying from Chicago to San Francisco Bay Area
Discover the top 9 airlines that operate flights from Chicago to San Francisco Bay Area. 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 March 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$83 | Average$212 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$382 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$120 | Average$235 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$128 | Average$374 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$423 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$159 | Average$304 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$304 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$197 | Average$537 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$208 | Average$434 | FlexibilityNo cancel fee | On-time69% |