$127+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Jun 20 — Jun 271
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
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 May 21, 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 May 21, 2026.
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 9/158:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Tue 9/2911:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 5/19![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/19:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Wed 7/87:55 pm
OAK
- MDW
1 stop7h 30m
Southwest
Deal found 5/20![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/85:35 am
MDW
- SFO
1 stop7h 50m
Southwest
Wed 7/1511:30 am
SFO
- MDW
1 stop8h 15m
Southwest
Deal found 5/17![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/14:25 pm
MDW
- SJC
1 stop8h 32m
Delta
Tue 7/2112:40 pm
SJC
- MDW
1 stop7h 35m
Delta
Deal found 5/18![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/77:40 pm
ORD
- SFO
1 stop6h 12m
Delta
Wed 7/159:55 am
SFO
- ORD
1 stop7h 02m
Delta
Deal found 5/17![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/16:30 am
ORD
- SJC
1 stop7h 35m
Delta
Tue 7/219:45 am
SJC
- ORD
1 stop7h 12m
Delta
Deal found 5/18![Delta logo]()
$277
This CheapOair deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/177:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Wed 6/2410:37 am
OAK
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/95:30 am
MDW
- OAK
1 stop6h 15m
Southwest
Tue 6/98:35 pm
OAK
- MDW
1 stop6h 45m
Southwest
Deal found 5/18![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/122:05 pm
MDW
- SJC
2 stops8h 15m
Southwest
Wed 8/268:45 am
SJC
- MDW
1 stop8h 30m
Southwest
Deal found 5/20![Southwest logo]()
$278
This Frontier deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:00 am
MDW
- SFO
1 stop15h 13m
Frontier
Sun 8/2310:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Deal found 5/20![Frontier logo]()
$280
This Frontier deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Sun 11/151:02 pm
ORD
- SFO
1 stop12h 48m
Frontier
Tue 11/174:00 pm
SFO
- ORD
1 stop11h 35m
Frontier
Deal found 5/20![Frontier logo]()
$280
This Cheapflightsfares deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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.
Tue 6/307:20 am
ORD
- SFO
1 stop8h 56m
Frontier
Sat 7/48:21 pm
SFO
- ORD
1 stop7h 58m
Frontier
Deal found 5/18![Frontier logo]()
$281
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 May 21, 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 May 21, 2026.
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/242:45 pm
ORD
- SJC
1 stop9h 31m
Delta
Tue 6/301:10 pm
SJC
- ORD
1 stop6h 15m
Delta
Deal found 5/17![Delta logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 7/226:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Wed 8/52:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 5/19![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 9/1712:05 pm
MDW
- SFO
1 stop7h 30m
Southwest
Sat 9/1911:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 5/19![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/1110:30 am
ORD
- SFO
Nonstop4h 45m
United Airlines
Sat 6/1311:30 pm
SFO
- ORD
Nonstop4h 23m
United Airlines
Deal found 5/16![United Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 8/56:25 am
ORD
- SJC
2 stops9h 48m
Delta
Tue 8/116:12 pm
SJC
- ORD
2 stops11h 44m
Delta
Deal found 5/16![Delta logo]()
$288
This Alaska Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/57:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Mon 8/108:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$292
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/48:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Tue 8/117:45 pm
OAK
- MDW
1 stop7h 55m
Southwest
Deal found 5/17![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 9/151:00 pm
MDW
- SFO
1 stop7h 48m
Delta
Mon 9/2110:45 pm
SFO
- MDW
1 stop7h 57m
Delta
Deal found 5/21![Delta logo]()
$292
This Alaska Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 8/86:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Mon 8/102:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 5/16![Alaska Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/298:15 pm
MDW
- SFO
1 stop6h 15m
Southwest
Tue 7/712:15 pm
SFO
- MDW
1 stop9h 05m
Southwest
Deal found 5/17![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/128:28 am
ORD
- SFO
1 stop6h 41m
Delta
Fri 8/1412:12 am
SFO
- ORD
1 stop6h 18m
Delta
Deal found 5/19![Delta logo]()
$292
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/308:50 am
ORD
- SFO
Nonstop4h 48m
United Airlines
Mon 7/2012:50 am
SFO
- ORD
Nonstop4h 26m
United Airlines
Deal found 5/16![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 9/1810:35 am
MDW
- SFO
2 stops9h 00m
Southwest
Tue 9/2211:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 5/20![Southwest logo]()
$320
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/163:57 pm
ORD
- SFO
Nonstop4h 52m
United Airlines
Sun 6/2111:30 pm
SFO
- ORD
Nonstop4h 23m
United Airlines
Deal found 5/18![United Airlines logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/196:01 am
ORD
- SJC
1 stop9h 29m
Alaska Airlines
Sat 8/2210:12 am
SJC
- ORD
1 stop6h 51m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 7/21:49 pm
MDW
- SFO
1 stop9h 11m
Delta
Mon 7/2012:35 am
SFO
- MDW
1 stop6h 02m
Delta
Deal found 5/16![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/145:35 am
MDW
- OAK
1 stop6h 15m
Southwest
Tue 7/215:15 am
OAK
- MDW
2 stops7h 20m
Southwest
Deal found 5/20![Southwest logo]()
$320
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/199:48 pm
ORD
- SFO
Nonstop4h 57m
United Airlines
Mon 6/2212:50 am
SFO
- ORD
Nonstop4h 26m
United Airlines
Deal found 5/19![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/286:30 am
ORD
- SFO
1 stop8h 39m
Delta
Mon 8/35:36 am
SFO
- ORD
1 stop8h 48m
Delta
Deal found 5/18![Delta logo]()
$316
This Alaska Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 8/85:59 pm
ORD
- SFO
1 stop7h 09m
Alaska Airlines
Mon 8/107:55 am
SFO
- ORD
1 stop9h 02m
Alaska Airlines
Deal found 5/16![Alaska Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 9/98:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Sun 9/135:25 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/21![Southwest logo]()
$332
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/256:10 am
ORD
- SFO
Nonstop4h 37m
United Airlines
Sun 6/286:34 pm
SFO
- ORD
Nonstop4h 25m
United Airlines
Deal found 5/17![United Airlines logo]()
$371
This Alaska Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/106:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Tue 7/72:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 7/29:40 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Mon 7/1311:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/16![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/87:45 am
ORD
- SJC
2 stops11h 27m
Delta
Mon 7/136:12 pm
SJC
- ORD
2 stops12h 18m
Delta
Deal found 5/20![Delta logo]()
$338
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/298:50 am
ORD
- SFO
Nonstop4h 48m
United Airlines
Tue 7/76:34 pm
SFO
- ORD
Nonstop4h 25m
United Airlines
Deal found 5/17![United Airlines logo]()
$385
This Alaska Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 9/192:22 pm
ORD
- STS
1 stop9h 04m
Alaska Airlines
Tue 9/227:03 am
STS
- ORD
1 stop8h 58m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/16:00 pm
MDW
- SJC
1 stop6h 20m
Southwest
Sun 7/58:00 pm
SJC
- MDW
1 stop6h 40m
Southwest
Deal found 5/21![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/46:00 am
MDW
- SJC
1 stop7h 36m
Delta
Wed 7/88:19 pm
SJC
- MDW
2 stops10h 18m
Delta
Deal found 5/18![Delta logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 8/85:59 pm
ORD
- STS
1 stop6h 59m
Alaska Airlines
Mon 8/105:56 pm
STS
- ORD
1 stop17h 25m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$359
Last-minute flights from Chicago to San Francisco Bay AreaDiscover last-minute flight deals from Chicago to San Francisco Bay Area. Data last updated May 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Francisco Bay Area. Data last updated May 21, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/36:55 am
ORD
- SFO
1 stop15h 02m
Frontier
Tue 6/910:58 pm
SFO
- ORD
1 stop28h 09m
Frontier
Deal found 5/19![Frontier logo]()
$287
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/95:30 am
MDW
- OAK
1 stop6h 15m
Southwest
Tue 6/98:35 pm
OAK
- MDW
1 stop6h 45m
Southwest
Deal found 5/18![Southwest logo]()
$277
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Tue 6/99:48 pm
ORD
- SFO
1 stop15h 55m
Frontier
Fri 6/1210:58 pm
SFO
- ORD
1 stop28h 09m
Frontier
Deal found 5/20![Frontier logo]()
$285
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/105:30 am
MDW
- SJC
1 stop6h 10m
Southwest
Tue 6/237:35 pm
SJC
- MDW
1 stop7h 05m
Southwest
Deal found 5/19![Southwest logo]()
$277
This CheapOair deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/177:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Wed 6/2410:37 am
OAK
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$277
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/177:30 am
ORD
- SFO
Nonstop4h 49m
United Airlines
Tue 8/46:34 pm
SFO
- ORD
Nonstop4h 25m
United Airlines
Deal found 5/18![United Airlines logo]()
$282
This Cheapflightsfares deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/189:48 pm
ORD
- SFO
1 stop28h 39m
Frontier
Wed 6/2410:58 pm
SFO
- ORD
1 stop28h 09m
Frontier
Deal found 5/18![Frontier logo]()
$286
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/199:48 pm
ORD
- SFO
1 stop28h 39m
Frontier
Tue 6/238:45 pm
SFO
- ORD
1 stop6h 22m
Frontier
Deal found 5/20![Frontier logo]()
$284
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- SJC
1 stop9h 16m
Delta
Wed 7/221:40 pm
SJC
- ORD
1 stop6h 08m
Delta
Deal found 5/18![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:35 am
ORD
- SFO
1 stop9h 51m
Delta
Tue 7/79:55 am
SFO
- ORD
1 stop7h 02m
Delta
Deal found 5/16![Delta logo]()
$277
This Cheapflightsfares deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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.
Tue 6/307:20 am
ORD
- SFO
1 stop8h 56m
Frontier
Sat 7/48:21 pm
SFO
- ORD
1 stop7h 58m
Frontier
Deal found 5/18![Frontier logo]()
$281
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/309:54 am
MDW
- SJC
2 stops9h 23m
Delta
Tue 7/2110:00 pm
SJC
- MDW
1 stop10h 05m
Delta
Deal found 5/18![Delta logo]()
$282
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 May 21, 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 May 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/47:20 am
ORD
- SJC
1 stop7h 57m
Frontier
Deal found 5/17![Frontier logo]()
$127
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/18:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/17![Southwest logo]()
$129
This United Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 9/18:59 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 5/21![United Airlines logo]()
$129
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/159:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/20![Southwest logo]()
$129
This Frontier deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Thu 7/26:00 am
MDW
- SFO
1 stop15h 26m
Frontier
Deal found 5/20![Frontier logo]()
$132
This Frontier deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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.
Thu 6/116:55 am
ORD
- SFO
1 stop15h 00m
Frontier
Deal found 5/19![Frontier logo]()
$132
This Super.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Thu 8/1312:11 pm
MDW
- SFO
1 stop9h 02m
Frontier
Deal found 5/20![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/19:48 pm
ORD
- SFO
1 stop28h 39m
Frontier
Deal found 5/20![Frontier logo]()
$133
This Frontier deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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.
Wed 8/1212:11 pm
MDW
- SFO
1 stop9h 02m
Frontier
Deal found 5/19![Frontier logo]()
$134
This Cheapflightsfares deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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.
Tue 6/167:20 am
ORD
- SFO
1 stop8h 56m
Frontier
Deal found 5/19![Frontier logo]()
$134
This Expedia deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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.
Tue 6/912:27 pm
MDW
- SFO
1 stop9h 28m
Frontier
Deal found 5/18![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 9/2911:06 am
ORD
- SJC
2 stops35h 02m
Frontier
Deal found 5/19![Frontier logo]()
$135
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 May 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (Southwest) |
One-way from | $127 (Kiwi.com) |
Popular in | February |
Cheapest in | September |
Average price | $373 |
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 May 21, 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
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Wed 6/24
2:45 pm-10:16 pm
1 stop9h 31m
San Jose
Tue 6/30
1:10 pm-9:25 pm
1 stop6h 15m
$277
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 7/22
6:20 am-2:10 pm
1 stop9h 50m
Oakland
Wed 8/5
2:50 pm-11:36 pm
1 stop6h 46m
$277
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Wed 8/5
6:25 am-2:13 pm
2 stops9h 48m
San Jose
Tue 8/11
6:12 pm-7:56 am
2 stops11h 44m
$288
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 8/5
7:59 pm-9:57 am
1 stop15h 58m
Oakland
Mon 8/10
8:10 pm-1:21 pm
1 stop15h 11m
$292
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 9/15
1:00 pm-6:48 pm
1 stop7h 48m
San Francisco
Mon 9/21
10:45 pm-8:42 am
1 stop7h 57m
$292
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Wed 8/12
8:28 am-1:09 pm
1 stop6h 41m
San Francisco
Fri 8/14
12:12 am-8:30 am
1 stop6h 18m
$292
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 9/17
12:05 pm-5:35 pm
1 stop7h 30m
San Francisco
Sat 9/19
11:40 pm-5:50 am
Nonstop4h 10m
$297
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Sat 8/8
6:20 am-2:10 pm
1 stop9h 50m
Oakland
Mon 8/10
2:50 pm-11:36 pm
1 stop6h 46m
$307
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 8/4
8:35 pm-11:05 pm
Nonstop4h 30m
Oakland
Tue 8/11
7:45 pm-5:40 am
1 stop7h 55m
$309
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 6/29
8:15 pm-12:30 am
1 stop6h 15m
San Francisco
Tue 7/7
12:15 pm-11:20 pm
1 stop9h 05m
$316
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.
ORD-SJC
MDW-SJC
MDW-OAK
MDW-SFO
ORD-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-SJC
MDW-OAK
MDW-SFO
What is the cheapest month to book a flight from Chicago to San Francisco Bay Area?
Currently, September is the cheapest month in which you can book a flight from Chicago to San Francisco Bay Area (average of $316). Flying from Chicago to San Francisco Bay Area in March is currently the most expensive (average of $482). 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 May 21, 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 afternoon. If you’re flexible enough to do this you can expect to save up to 12% on your trip compared to booking a flight in the morning.
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 May 21, 2026.
The most flights from CHI to zzXIH are scheduled on a Thursday (96 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (56 on average).
How far ahead should I book a flight from Chicago to San Francisco Bay Area?
Booking 55 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Francisco Bay Area. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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 May 16, 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.
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 May 21, 2026.
Read reviews from past customers who have flown Alaska Airlines,Southwest, 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
7.8
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Crew
8.5
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Comfort
7.8
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Crew
8.5
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Comfort
7.8
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Crew
8.5
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Comfort
7.8
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Crew
8.5
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Comfort
7.8
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Crew
8.5
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Comfort
7.8
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Crew
8.5
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
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 May 21, 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 8 airlines flying from Chicago to San Francisco Bay Area
Discover the top 8 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 May 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$217 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$128 | Average$371 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$431 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$147 | Average$264 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$165 | Average$384 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$199 | Average$570 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$224 | Average$460 | FlexibilityNo cancel fee | On-time69% |