$81+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Mar 5 — Mar 121
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
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.Cheap flight deals from Chicago to San Francisco Bay Area
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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 February 3, 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 February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/45:15 am
ORD
- SJC
2 stops38h 29m
Multiple Airlines
Mon 3/98:20 pm
SJC
- ORD
1 stop7h 48m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Wed 3/411:51 am
ORD
- SJC
2 stops31h 53m
Frontier
Mon 3/98:20 pm
SJC
- ORD
1 stop7h 48m
Frontier
Deal found 1/31![Frontier logo]()
$192
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/243:52 pm
ORD
- SJC
1 stop9h 03m
Multiple Airlines
Mon 4/278:20 pm
SJC
- ORD
1 stop8h 27m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$207
This CheapOair deal was found by Cheapflights users on 2/3. 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.
Wed 3/48:20 am
ORD
- SJC
1 stop11h 13m
Alaska Airlines
Thu 3/57:00 am
SJC
- ORD
1 stop14h 59m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Tue 3/36:02 pm
ORD
- SJC
2 stops41h 37m
Frontier
Mon 3/98:20 pm
SJC
- ORD
1 stop7h 48m
Frontier
Deal found 2/1![Frontier logo]()
$217
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 2/2411:10 am
MDW
- OAK
Nonstop4h 55m
Southwest
Sat 3/145:40 am
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 2/2![Southwest logo]()
$217
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/23:54 pm
ORD
- SJC
1 stop9h 05m
Multiple Airlines
Mon 3/98:20 pm
SJC
- ORD
1 stop7h 48m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$219
This CheapOair deal was found by Cheapflights users on 1/31. 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.
Sat 4/187:21 pm
ORD
- SJC
1 stop26h 04m
Frontier
Thu 4/236:57 pm
SJC
- ORD
1 stop9h 50m
Frontier
Deal found 1/31![Frontier logo]()
$222
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Thu 4/303:52 pm
ORD
- SJC
1 stop9h 03m
Alaska Airlines
Wed 5/610:21 am
SJC
- ORD
1 stop6h 42m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$223
This CheapOair deal was found by Cheapflights users on 2/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:59 pm
ORD
- OAK
1 stop16h 18m
Alaska Airlines
Mon 5/116:55 pm
OAK
- ORD
1 stop16h 18m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 4/83:29 pm
ORD
- SJC
2 stops29h 33m
Frontier
Mon 4/1310:29 am
SJC
- ORD
1 stop18h 18m
Frontier
Deal found 2/2![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 4/159:18 pm
ORD
- SJC
1 stop22h 44m
Frontier
Sun 4/198:20 pm
SJC
- ORD
1 stop8h 27m
Frontier
Deal found 2/2![Frontier logo]()
$230
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 February 3, 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 February 3, 2026.
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 2/2411:10 am
MDW
- OAK
Nonstop4h 55m
Southwest
Sat 3/145:40 am
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 2/2![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:45 pm
ORD
- OAK
1 stop7h 06m
Delta
Tue 3/1012:35 pm
OAK
- ORD
1 stop6h 59m
Delta
Deal found 2/2![Delta logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 2/253:54 pm
ORD
- OAK
1 stop8h 55m
Alaska Airlines
Sat 2/286:15 am
OAK
- ORD
1 stop8h 18m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$237
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Wed 2/256:25 am
ORD
- SFO
Nonstop5h 02m
United Airlines
Mon 3/211:59 pm
SFO
- ORD
Nonstop4h 20m
United Airlines
Deal found 2/2![United Airlines logo]()
$250
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 3/149:40 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Tue 3/1711:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 2/2![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 1/31. 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.
Sat 2/288:55 pm
MDW
- OAK
Nonstop4h 55m
Southwest
Sat 3/711:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 1/31![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 2/3. 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.
Sun 3/16:45 pm
ORD
- OAK
1 stop7h 06m
Delta
Thu 3/55:55 am
OAK
- ORD
2 stops10h 06m
Delta
Deal found 2/3![Delta logo]()
$242
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:20 am
ORD
- SJC
1 stop7h 53m
Alaska Airlines
Tue 3/1010:24 am
SJC
- ORD
1 stop26h 34m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$253
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:25 am
ORD
- OAK
2 stops12h 47m
Delta
Tue 3/104:49 pm
OAK
- ORD
2 stops13h 41m
Delta
Deal found 2/2![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 2/2411:10 am
MDW
- OAK
Nonstop4h 55m
Southwest
Thu 3/128:30 pm
OAK
- MDW
1 stop6h 05m
Southwest
Deal found 2/2![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 1/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:17 am
ORD
- SFO
Nonstop5h 05m
United Airlines
Sat 3/216:44 pm
SFO
- ORD
Nonstop4h 15m
United Airlines
Deal found 1/31![United Airlines logo]()
$282
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Mon 3/23:54 pm
ORD
- SJC
1 stop9h 05m
Alaska Airlines
Tue 3/1012:45 pm
SJC
- ORD
1 stop9h 14m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$263
This Delta deal was found by Cheapflights users on 2/3. 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 2/241:49 pm
MDW
- OAK
2 stops12h 02m
Delta
Tue 3/35:55 am
OAK
- MDW
2 stops9h 42m
Delta
Deal found 2/3![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1510:45 pm
ORD
- SFO
Nonstop4h 50m
United Airlines
Sun 5/1711:56 pm
SFO
- ORD
Nonstop4h 24m
United Airlines
Deal found 2/1![United Airlines logo]()
$283
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 4/18:20 am
ORD
- SJC
1 stop7h 38m
Alaska Airlines
Mon 4/67:05 pm
SJC
- ORD
1 stop9h 34m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$263
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 2/288:15 am
MDW
- SFO
Nonstop5h 00m
Southwest
Sat 3/75:15 am
SFO
- MDW
Nonstop3h 55m
Southwest
Deal found 2/2![Southwest logo]()
$250
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:37 pm
ORD
- SFO
1 stop7h 48m
Delta
Tue 3/32:05 pm
SFO
- ORD
1 stop7h 51m
Delta
Deal found 2/2![Delta logo]()
$252
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Fri 3/66:17 am
ORD
- SFO
Nonstop5h 05m
United Airlines
Mon 3/166:44 pm
SFO
- ORD
Nonstop4h 15m
United Airlines
Deal found 2/2![United Airlines logo]()
$283
This Alaska Airlines deal was found by Cheapflights users on 2/3. 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.
Wed 2/253:54 pm
ORD
- OAK
1 stop8h 55m
Alaska Airlines
Mon 3/25:03 pm
OAK
- ORD
1 stop18h 08m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$268
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/167:10 pm
ORD
- SFO
1 stop6h 49m
Delta
Tue 3/175:50 am
SFO
- ORD
1 stop8h 53m
Delta
Deal found 2/1![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 1/31. 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.
Sat 4/186:00 am
MDW
- SFO
1 stop6h 25m
Southwest
Tue 4/282:50 pm
SFO
- MDW
1 stop6h 30m
Southwest
Deal found 1/31![Southwest logo]()
$254
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Thu 3/127:45 am
ORD
- SFO
Nonstop5h 10m
United Airlines
Sun 3/2211:59 pm
SFO
- ORD
Nonstop4h 20m
United Airlines
Deal found 2/2![United Airlines logo]()
$288
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:59 pm
ORD
- SJC
1 stop17h 47m
Alaska Airlines
Wed 3/2510:22 am
SJC
- ORD
1 stop11h 37m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 1/31. 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.
Sun 3/15:37 pm
ORD
- SFO
1 stop7h 48m
Delta
Tue 3/310:00 pm
SFO
- ORD
1 stop8h 41m
Delta
Deal found 1/31![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 2/2. 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 4/29:30 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Mon 4/68:30 pm
OAK
- MDW
1 stop6h 05m
Southwest
Deal found 2/2![Southwest logo]()
$258
This United Airlines deal was found by Cheapflights users on 1/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:31 pm
ORD
- SFO
Nonstop4h 59m
United Airlines
Mon 5/2510:45 pm
SFO
- ORD
Nonstop4h 23m
United Airlines
Deal found 1/31![United Airlines logo]()
$298
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:00 am
ORD
- SJC
1 stop9h 35m
Alaska Airlines
Wed 3/2510:22 am
SJC
- ORD
1 stop11h 37m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:55 am
MDW
- OAK
1 stop6h 40m
Southwest
Mon 3/95:45 am
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 2/1![Southwest logo]()
$258
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:20 pm
MDW
- SFO
1 stop6h 27m
Delta
Sun 3/15:45 am
SFO
- MDW
1 stop9h 52m
Delta
Deal found 2/1![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 2/2. 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 3/910:05 am
MDW
- SFO
1 stop8h 00m
Southwest
Wed 3/115:40 am
SFO
- MDW
Nonstop4h 00m
Southwest
Deal found 2/2![Southwest logo]()
$260
Last-minute flights from Chicago to San Francisco Bay AreaDiscover last-minute flight deals from Chicago to San Francisco Bay Area. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Francisco Bay Area. Data last updated February 3, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 2/2411:10 am
MDW
- OAK
Nonstop4h 55m
Southwest
Sat 3/145:40 am
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 2/2![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 2/245:05 am
MDW
- OAK
1 stop7h 00m
Southwest
Thu 3/128:30 pm
OAK
- MDW
1 stop6h 05m
Southwest
Deal found 2/2![Southwest logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 2/253:54 pm
ORD
- OAK
1 stop8h 55m
Alaska Airlines
Sat 2/286:15 am
OAK
- ORD
1 stop8h 18m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$237
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/23:54 pm
ORD
- SJC
1 stop9h 05m
Multiple Airlines
Mon 3/98:20 pm
SJC
- ORD
1 stop7h 48m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 2/3. 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 3/28:00 am
MDW
- OAK
2 stops8h 20m
Southwest
Tue 3/105:50 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 2/3![Southwest logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/23:54 pm
ORD
- SJC
1 stop9h 05m
Hawaiian Airlines
Tue 3/312:45 pm
SJC
- ORD
1 stop9h 14m
Hawaiian Airlines
Deal found 2/2![Hawaiian Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Tue 3/36:02 pm
ORD
- SJC
2 stops41h 37m
Frontier
Mon 3/98:20 pm
SJC
- ORD
1 stop7h 48m
Frontier
Deal found 2/1![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/38:20 am
ORD
- SJC
1 stop7h 53m
Hawaiian Airlines
Tue 3/38:05 pm
SJC
- ORD
1 stop16h 53m
Hawaiian Airlines
Deal found 2/2![Hawaiian Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/45:15 am
ORD
- SJC
2 stops38h 29m
Multiple Airlines
Mon 3/98:20 pm
SJC
- ORD
1 stop7h 48m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Wed 3/411:51 am
ORD
- SJC
2 stops31h 53m
Frontier
Mon 3/98:20 pm
SJC
- ORD
1 stop7h 48m
Frontier
Deal found 1/31![Frontier logo]()
$192
This CheapOair deal was found by Cheapflights users on 2/3. 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.
Wed 3/48:20 am
ORD
- SJC
1 stop11h 13m
Alaska Airlines
Thu 3/57:00 am
SJC
- ORD
1 stop14h 59m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$210
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/53:07 pm
ORD
- SJC
1 stop9h 49m
Alaska Airlines
Mon 3/912:45 pm
SJC
- ORD
1 stop9h 14m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$223
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 February 3, 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 February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:53 pm
ORD
- SJC
1 stop23h 09m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$81
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 3/149:40 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/2![Southwest logo]()
$90
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Tue 3/244:10 pm
ORD
- STS
1 stop9h 03m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:25 am
MDW
- SJC
2 stops32h 42m
Frontier
Deal found 2/3![Frontier logo]()
$99
This CheapOair deal was found by Cheapflights users on 2/3. 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.
Wed 3/113:07 pm
ORD
- SJC
1 stop9h 49m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$99
This Expedia deal was found by Cheapflights users on 2/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/223:52 pm
ORD
- OAK
1 stop8h 31m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$99
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 4/47:20 pm
ORD
- OAK
1 stop7h 35m
Southwest
Deal found 2/2![Southwest logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/1111:25 am
MDW
- SJC
2 stops32h 42m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$101
This Mytrip deal was found by Cheapflights users on 2/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/118:55 pm
ORD
- SJC
1 stop23h 12m
Frontier
Deal found 2/1![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 5/116:15 am
MDW
- SJC
2 stops13h 47m
Frontier
Deal found 2/2![Frontier logo]()
$102
This CheapOair deal was found by Cheapflights users on 2/3. 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.
Wed 3/48:20 am
ORD
- SJC
1 stop11h 13m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Wed 3/2512:35 pm
ORD
- SJC
1 stop31h 32m
Frontier
Deal found 1/31![Frontier logo]()
$107
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 February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $190 (Kiwi.com) |
One-way from | $81 (Kiwi.com) |
Popular in | December |
Cheapest in | July |
Average price | $315 |
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 February 3, 2026.
Use the filters below to find and compare flights from Chicago to San Francisco Bay Area that are best for you.
Fly from
Chicago
Fly to
San Francisco Bay Area
Route
Depart
Return
Price
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 2/24
11:10 am-2:05 pm
Nonstop4h 55m
Oakland
Sat 3/14
5:40 am-11:40 am
Nonstop4h 00m
$217
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Sat 3/14
9:40 pm-12:20 am
Nonstop4h 40m
Oakland
Tue 3/17
11:55 pm-5:55 am
Nonstop4h 00m
$217
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Sat 2/28
8:55 pm-11:50 pm
Nonstop4h 55m
Oakland
Sat 3/7
11:55 pm-5:55 am
Nonstop4h 00m
$217
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 2/24
11:10 am-2:05 pm
Nonstop4h 55m
Oakland
Thu 3/12
8:30 pm-4:35 am
1 stop6h 05m
$227
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Mon 3/2
6:45 pm-11:51 pm
1 stop7h 06m
Oakland
Tue 3/10
12:35 pm-9:34 pm
1 stop6h 59m
$237
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 2/25
3:54 pm-10:49 pm
1 stop8h 55m
Oakland
Sat 2/28
6:15 am-4:33 pm
1 stop8h 18m
$237
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Sun 3/1
6:45 pm-11:51 pm
1 stop7h 06m
Oakland
Thu 3/5
5:55 am-6:01 pm
2 stops10h 06m
$242
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Tue 3/3
5:25 am-4:12 pm
2 stops12h 47m
Oakland
Tue 3/10
4:49 pm-8:30 am
2 stops13h 41m
$247
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 2/24
1:49 pm-11:51 pm
2 stops12h 02m
Oakland
Tue 3/3
5:55 am-5:37 pm
2 stops9h 42m
$247
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Wed 2/25
6:25 am-9:27 am
Nonstop5h 02m
San Francisco
Mon 3/2
11:59 pm-6:19 am
Nonstop4h 20m
$250
Showing 1-10 of 60 results
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.
ORD-SJC
MDW-OAK
ORD-OAK
ORD-SFO
MDW-SFO
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
ORD-SJC
MDW-OAK
ORD-OAK
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 November is currently the most expensive (average of $207). 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 February 3, 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 25% 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 January 31, 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. Sunday 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 February 3, 2026.
The most flights from CHI to zzXIH are scheduled on a Monday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 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 February 3, 2026.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and United 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.
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
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 February 3, 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 10 airlines flying from Chicago to San Francisco Bay Area
Discover the top 10 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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$53 | Average$215 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$80 | Average$212 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$382 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$112 | Average$374 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$128 | Average$349 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$427 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$183 | Average$304 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$187 | Average$324 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$197 | Average$543 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$428 | FlexibilityNo cancel fee | On-time69% |