$66+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from San Francisco Bay Area to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from San Francisco Bay Area to Chicago
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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 February 3, 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 February 3, 2026.
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.
Sat 5/27:23 am
STS
- ORD
1 stop9h 40m
Alaska Airlines
Thu 5/73:52 pm
ORD
- STS
1 stop9h 35m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$210
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.
Sat 5/27:23 am
STS
- ORD
1 stop9h 40m
Alaska Airlines
Wed 5/66:00 am
ORD
- STS
1 stop8h 21m
Alaska Airlines
Deal found 2/2![Alaska Airlines 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.
Sat 3/75:40 am
OAK
- MDW
Nonstop4h 00m
Southwest
Sat 3/149:40 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/2![Southwest 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.
Thu 5/76:57 pm
SJC
- ORD
1 stop8h 34m
Multiple Airlines
Sun 5/109:18 pm
ORD
- SJC
1 stop22h 44m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$217
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:15 am
OAK
- ORD
1 stop8h 18m
Alaska Airlines
Sat 3/75:29 pm
ORD
- OAK
1 stop8h 25m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$217
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:57 pm
SJC
- ORD
1 stop9h 50m
Multiple Airlines
Tue 4/283:52 pm
ORD
- SJC
1 stop19h 52m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$218
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.
Tue 4/143:00 pm
OAK
- ORD
1 stop6h 55m
Southwest
Sat 4/184:15 pm
ORD
- OAK
1 stop6h 45m
Southwest
Deal found 2/1![Southwest logo]()
$218
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 4/223:18 pm
OAK
- ORD
1 stop25h 45m
Alaska Airlines
Thu 4/303:52 pm
ORD
- OAK
1 stop8h 31m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$220
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:02 pm
SJC
- ORD
1 stop7h 47m
Multiple Airlines
Thu 3/127:40 am
ORD
- SJC
1 stop8h 36m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$221
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:00 am
STS
- ORD
1 stop10h 02m
Alaska Airlines
Wed 4/154:10 pm
ORD
- STS
1 stop9h 03m
Alaska Airlines
Deal found 1/31![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.
Tue 2/247:00 am
SJC
- ORD
1 stop14h 59m
Alaska Airlines
Wed 2/258:20 am
ORD
- SJC
1 stop11h 13m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$223
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:41 am
OAK
- ORD
1 stop10h 22m
Alaska Airlines
Mon 4/277:59 pm
ORD
- OAK
1 stop16h 18m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$223
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 February 3, 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 February 3, 2026.
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.
Sat 5/27:23 am
STS
- ORD
1 stop9h 40m
Alaska Airlines
Wed 5/66:00 am
ORD
- STS
1 stop8h 21m
Alaska Airlines
Deal found 2/2![Alaska Airlines 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.
Mon 3/28:30 pm
OAK
- MDW
1 stop6h 35m
Southwest
Fri 3/69:30 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/2![Southwest logo]()
$227
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.
Sat 4/115:55 am
OAK
- ORD
1 stop7h 23m
Delta
Tue 4/217:12 pm
ORD
- OAK
1 stop6h 42m
Delta
Deal found 1/31![Delta logo]()
$237
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.
Tue 4/2112:45 am
SFO
- ORD
Nonstop4h 22m
United Airlines
Sun 4/266:25 am
ORD
- SFO
Nonstop4h 51m
United Airlines
Deal found 2/1![United Airlines logo]()
$250
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.
Fri 3/69:39 pm
SFO
- RFD
1 stop11h 34m
Multiple Airlines
Mon 3/99:41 pm
RFD
- SFO
2 stops22h 56m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$405
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:00 am
STS
- ORD
1 stop10h 02m
Alaska Airlines
Wed 4/154:10 pm
ORD
- STS
1 stop9h 03m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$223
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 5/28:05 am
OAK
- MDW
1 stop7h 45m
Southwest
Wed 5/68:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/2![Southwest logo]()
$227
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 3/1012:35 pm
OAK
- ORD
1 stop6h 59m
Delta
Tue 3/177:10 pm
ORD
- OAK
1 stop6h 36m
Delta
Deal found 2/2![Delta logo]()
$237
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:00 am
STS
- ORD
1 stop10h 02m
Alaska Airlines
Tue 4/74:10 pm
ORD
- STS
1 stop9h 03m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$223
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 5/612:45 am
SFO
- ORD
Nonstop4h 22m
United Airlines
Sun 5/1010:45 pm
ORD
- SFO
Nonstop4h 50m
United Airlines
Deal found 2/2![United Airlines logo]()
$264
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.
Thu 3/55:55 am
OAK
- ORD
2 stops10h 06m
Delta
Tue 3/107:10 pm
ORD
- OAK
1 stop6h 36m
Delta
Deal found 2/2![Delta logo]()
$242
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:21 am
SJC
- ORD
1 stop6h 42m
Alaska Airlines
Fri 5/83:52 pm
ORD
- SJC
1 stop9h 03m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$223
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.
Wed 3/42:35 pm
SFO
- MDW
1 stop6h 15m
Southwest
Wed 3/119:05 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 2/3![Southwest logo]()
$247
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 5/710:55 pm
SFO
- ORD
Nonstop4h 30m
United Airlines
Tue 5/126:20 am
ORD
- SFO
Nonstop4h 51m
United Airlines
Deal found 2/2![United Airlines logo]()
$265
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 3/312:40 pm
OAK
- ORD
1 stop7h 12m
Delta
Tue 3/106:15 am
ORD
- OAK
2 stops11h 45m
Delta
Deal found 2/2![Delta logo]()
$242
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 3/55:45 am
OAK
- MDW
Nonstop4h 00m
Southwest
Tue 3/109:00 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/2![Southwest logo]()
$247
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 3/177:57 pm
STS
- ORD
1 stop8h 42m
Alaska Airlines
Tue 3/314:13 pm
ORD
- STS
1 stop9h 00m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$230
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.
Wed 3/411:10 am
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 3/79:40 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 1/31![Southwest logo]()
$248
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.
Wed 2/255:45 am
SFO
- MDW
1 stop9h 52m
Delta
Thu 2/267:20 pm
MDW
- SFO
1 stop6h 27m
Delta
Deal found 2/1![Delta logo]()
$252
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/22:09 pm
OAK
- ORD
1 stop7h 50m
Alaska Airlines
Sat 5/98:50 am
ORD
- OAK
1 stop7h 48m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$230
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.
Wed 4/812:45 am
SFO
- ORD
Nonstop4h 22m
United Airlines
Mon 4/139:20 pm
ORD
- SFO
Nonstop4h 59m
United Airlines
Deal found 2/1![United Airlines logo]()
$298
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.
Fri 3/65:10 am
SFO
- MDW
Nonstop4h 00m
Southwest
Tue 3/1010:05 am
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 2/3![Southwest logo]()
$250
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.
Wed 3/42:39 pm
SFO
- ORD
1 stop7h 13m
Delta
Fri 3/65:37 pm
ORD
- SFO
1 stop7h 48m
Delta
Deal found 2/1![Delta logo]()
$252
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:09 pm
OAK
- ORD
1 stop7h 50m
Alaska Airlines
Tue 5/199:00 am
ORD
- OAK
1 stop7h 32m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$230
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.
Mon 2/2310:50 pm
SFO
- ORD
Nonstop4h 22m
United Airlines
Sun 3/16:25 am
ORD
- SFO
Nonstop5h 05m
United Airlines
Deal found 2/2![United Airlines logo]()
$305
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.
Tue 4/1411:10 am
OAK
- ORD
2 stops9h 45m
Southwest
Sat 4/183:05 pm
ORD
- OAK
1 stop8h 40m
Southwest
Deal found 2/1![Southwest 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.
Fri 4/249:35 pm
SFO
- MDW
1 stop10h 21m
Delta
Mon 4/279:27 am
MDW
- SFO
1 stop7h 28m
Delta
Deal found 2/2![Delta logo]()
$267
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/132:35 pm
SJC
- ORD
1 stop7h 24m
Alaska Airlines
Wed 4/228:50 am
ORD
- SJC
1 stop7h 18m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$250
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.
Sat 3/216:44 pm
SFO
- ORD
Nonstop4h 15m
United Airlines
Tue 3/247:45 am
ORD
- SFO
Nonstop5h 10m
United Airlines
Deal found 2/2![United Airlines logo]()
$307
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.
Sat 3/219:55 pm
OAK
- MDW
1 stop5h 45m
Southwest
Thu 3/269:30 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/3![Southwest logo]()
$257
Last-minute flights from San Francisco Bay Area to ChicagoDiscover last-minute flight deals from San Francisco Bay Area to Chicago. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco Bay Area to Chicago. Data last updated February 3, 2026 and is based on user searches.
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.
Thu 2/2610:34 am
SJC
- ORD
1 stop28h 52m
Multiple Airlines
Tue 3/38:16 pm
ORD
- SJC
2 stops47h 28m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$235
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:15 am
OAK
- ORD
1 stop8h 18m
Alaska Airlines
Sat 3/75:29 pm
ORD
- OAK
1 stop8h 25m
Alaska Airlines
Deal found 2/2![Alaska Airlines 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.
Mon 3/28:30 pm
OAK
- MDW
1 stop6h 35m
Southwest
Fri 3/69:30 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/2![Southwest logo]()
$227
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 3/32:50 pm
SJC
- ORD
1 stop7h 09m
Alaska Airlines
Tue 3/108:20 am
ORD
- SJC
1 stop7h 53m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$223
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 3/312:40 pm
OAK
- ORD
1 stop7h 12m
Delta
Tue 3/107:10 pm
ORD
- OAK
1 stop6h 36m
Delta
Deal found 2/2![Delta logo]()
$237
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.
Wed 3/46:55 pm
OAK
- MDW
1 stop8h 00m
Southwest
Sat 3/78:10 pm
MDW
- OAK
1 stop6h 45m
Southwest
Deal found 1/31![Southwest logo]()
$237
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 3/75:40 am
OAK
- MDW
Nonstop4h 00m
Southwest
Sat 3/149:40 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/2![Southwest logo]()
$217
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:02 pm
SJC
- ORD
1 stop7h 47m
Multiple Airlines
Thu 3/127:40 am
ORD
- SJC
1 stop8h 36m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$221
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 3/1411:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Sat 3/219:40 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/2![Southwest logo]()
$228
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 3/177:57 pm
STS
- ORD
1 stop8h 42m
Alaska Airlines
Tue 3/314:13 pm
ORD
- STS
1 stop9h 00m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$230
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:42 pm
SJC
- ORD
1 stop8h 26m
Multiple Airlines
Wed 4/18:20 am
ORD
- SJC
1 stop7h 38m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$203
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:00 am
STS
- ORD
1 stop10h 02m
Alaska Airlines
Wed 4/84:10 pm
ORD
- STS
1 stop9h 03m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$223
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 February 3, 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 February 3, 2026.
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/98:20 pm
SJC
- ORD
1 stop7h 48m
Frontier
Deal found 2/1![Frontier logo]()
$66
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 5/118:20 pm
SJC
- ORD
1 stop8h 27m
Frontier
Deal found 2/2![Frontier logo]()
$74
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:20 pm
SJC
- ORD
1 stop8h 27m
Frontier
Deal found 2/3![Frontier logo]()
$76
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.
Mon 5/48:20 pm
SJC
- ORD
1 stop8h 27m
Frontier
Deal found 2/3![Frontier logo]()
$81
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/167:42 pm
SJC
- ORD
1 stop8h 26m
Frontier
Deal found 2/3![Frontier logo]()
$88
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.
Sun 4/198:20 pm
SJC
- ORD
1 stop8h 27m
Frontier
Deal found 2/2![Frontier logo]()
$89
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 2/286:40 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 2/2![Southwest logo]()
$90
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:32 pm
SJC
- ORD
1 stop7h 07m
Frontier
Deal found 2/3![Frontier logo]()
$95
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.
Sun 3/18:57 pm
SJC
- MDW
2 stops24h 57m
Frontier
Deal found 2/2![Frontier logo]()
$96
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 3/237:42 pm
SJC
- ORD
1 stop8h 26m
Frontier
Deal found 2/2![Frontier logo]()
$98
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:00 am
STS
- ORD
1 stop10h 02m
Alaska Airlines
Deal found 2/3![Alaska Airlines 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.
Tue 3/32:50 pm
SJC
- ORD
1 stop7h 09m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$99
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 February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $197 (Alaska Airlines) |
One-way from | $66 (Trip.com) |
Popular in | November |
Cheapest in | September |
Average price | $297 |
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 February 3, 2026.
Use the filters below to find and compare flights from San Francisco Bay Area to Chicago that are best for you.
Fly from
San Francisco Bay Area
Fly to
Chicago
Route
Depart
Return
Price
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Sat 5/2
7:23 am-7:03 pm
1 stop9h 40m
Chicago O'Hare Intl
Wed 5/6
6:00 am-12:21 pm
1 stop8h 21m
$217
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Wed 4/8
7:00 am-7:02 pm
1 stop10h 02m
Chicago O'Hare Intl
Wed 4/15
4:10 pm-11:13 pm
1 stop9h 03m
$223
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Mon 3/23
7:00 am-7:02 pm
1 stop10h 02m
Chicago O'Hare Intl
Tue 4/7
4:10 pm-11:13 pm
1 stop9h 03m
$223
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 5/6
10:21 am-7:03 pm
1 stop6h 42m
Chicago O'Hare Intl
Fri 5/8
3:52 pm-10:55 pm
1 stop9h 03m
$223
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Mon 3/2
8:30 pm-5:05 am
1 stop6h 35m
Chicago Midway
Fri 3/6
9:30 pm-12:10 am
Nonstop4h 40m
$227
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 5/2
8:05 am-5:50 pm
1 stop7h 45m
Chicago Midway
Wed 5/6
8:50 pm-11:25 pm
Nonstop4h 35m
$227
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Tue 3/17
7:57 pm-6:39 am
1 stop8h 42m
Chicago O'Hare Intl
Tue 3/31
4:13 pm-11:13 pm
1 stop9h 00m
$230
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sat 5/2
2:09 pm-11:59 pm
1 stop7h 50m
Chicago O'Hare Intl
Sat 5/9
8:50 am-2:38 pm
1 stop7h 48m
$230
OaklandChicago
OAK - ORD
OAKORD
Oakland
Tue 5/12
2:09 pm-11:59 pm
1 stop7h 50m
Chicago O'Hare Intl
Tue 5/19
9:00 am-2:32 pm
1 stop7h 32m
$230
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sat 4/11
5:55 am-3:18 pm
1 stop7h 23m
Chicago O'Hare Intl
Tue 4/21
7:12 pm-11:54 pm
1 stop6h 42m
$237
Showing 1-10 of 60 results
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.
SJC-ORD
OAK-MDW
OAK-ORD
STS-ORD
SJC-MDW
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
SJC-ORD
OAK-MDW
OAK-ORD
STS-ORD
What is the cheapest month to book a flight from San Francisco Bay Area to Chicago?
Currently, October is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago (average of $125). 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 February 3, 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 32% 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 January 31, 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 February 3, 2026.
The most flights from zzXIH to CHI are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 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 February 3, 2026.
See what other customers who have flown with Alaska Airlines, Southwest, and United 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
7.0
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
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 February 3, 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 February 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
San Francisco Bay Area to Chicago flights
Consider these flights traveling from San Francisco Bay Area to Chicago.
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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$241 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$101 | Average$277 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$108 | Average$230 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$128 | Average$351 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$133 | Average$422 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$170 | Average$397 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$185 | Average$427 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$197 | Average$443 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$275 | FlexibilityNo cancel fee | On-time62% |