$160+ Cheap flights from San Jose, CA (SJC) 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Aug 31 — Sep 71
Round-trip
1 adult, Economy
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Find cheap flights from San Jose 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.Cheapflights Tip: The best prices from San Jose to Chicago are usually found in February or April, booked 79 days in advance, depart on a Wednesday or Saturday and return on a Tuesday
Cheap flight deals from San Jose to Chicago
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Best
Last-minute
One-way
Cheapest flights from San Jose to ChicagoExplore the most affordable flight options available from San Jose to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.
Explore the most affordable flight options available from San Jose to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Sat 8/296:20 am
SJC
- ORD
Nonstop4h 25m
United Airlines
Sat 9/56:00 am
ORD
- SJC
1 stop9h 08m
United Airlines
Deal found 8/1![United Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Tue 8/258:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/28![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Tue 8/258:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/28![United Airlines logo]()
$315
This Frontier deal was found by Cheapflights users on 8/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:24 pm
SJC
- ORD
1 stop13h 18m
Frontier
Thu 10/226:50 am
ORD
- SJC
1 stop8h 39m
Frontier
Deal found 8/1![Frontier logo]()
$316
This Southwest deal was found by Cheapflights users on 7/31. 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 9/511:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Fri 9/118:50 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 7/31![Southwest logo]()
$317
This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/183:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Fri 8/282:18 pm
ORD
- SJC
1 stop6h 51m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$317
This CheapOair deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:38 pm
SJC
- ORD
1 stop14h 00m
Frontier
Sun 9/278:55 pm
ORD
- SJC
1 stop17h 48m
Frontier
Deal found 7/30![Frontier logo]()
$318
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:05 am
SJC
- MDW
1 stop8h 34m
Delta
Mon 11/161:00 pm
MDW
- SJC
1 stop11h 08m
Delta
Deal found 7/30![Delta logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:03 pm
SJC
- ORD
2 stops25h 20m
Frontier
Thu 9/178:55 pm
ORD
- SJC
1 stop17h 48m
Frontier
Deal found 7/28![Frontier logo]()
$319
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Fri 9/188:50 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 7/28![Southwest logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Mon 9/72:17 pm
SJC
- ORD
1 stop26h 04m
Frontier
Mon 9/146:30 am
ORD
- SJC
2 stops15h 23m
Frontier
Deal found 8/1![Frontier logo]()
$320
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:35 am
SJC
- MDW
1 stop5h 55m
Southwest
Thu 11/1910:15 am
MDW
- SJC
Nonstop4h 45m
Southwest
Deal found 7/29![Southwest logo]()
$321
Best flights from San Jose to ChicagoDiscover carefully curated flight deals from San Jose to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
Discover carefully curated flight deals from San Jose to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Tue 8/256:50 am
MDW
- SJC
1 stop6h 30m
Southwest
Deal found 7/27![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2110:20 pm
SJC
- MDW
1 stop9h 50m
Delta
Tue 9/11:51 pm
MDW
- SJC
1 stop8h 33m
Delta
Deal found 7/30![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Mon 8/318:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/28![United Airlines logo]()
$337
This Alaska Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:03 am
SJC
- ORD
1 stop6h 54m
Alaska Airlines
Tue 8/182:20 pm
ORD
- SJC
1 stop6h 51m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:15 am
SJC
- MDW
1 stop6h 45m
Southwest
Tue 9/18:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/29![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:37 pm
SJC
- MDW
1 stop7h 59m
Delta
Fri 8/286:05 am
MDW
- SJC
1 stop7h 17m
Delta
Deal found 7/30![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/272:08 pm
SJC
- ORD
Nonstop4h 27m
United Airlines
Wed 9/309:14 am
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/28![United Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2311:58 am
SJC
- RFD
1 stop21h 39m
Multiple Airlines
Tue 12/299:02 pm
RFD
- SJC
1 stop16h 01m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$702
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:40 am
SJC
- MDW
2 stops7h 10m
Southwest
Mon 10/56:15 pm
MDW
- SJC
1 stop7h 40m
Southwest
Deal found 7/30![Southwest logo]()
$328
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/810:12 am
SJC
- ORD
1 stop7h 09m
Alaska Airlines
Tue 9/158:00 am
ORD
- SJC
2 stops10h 25m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:51 pm
SJC
- MDW
1 stop7h 53m
Delta
Tue 10/612:45 pm
MDW
- SJC
1 stop10h 40m
Delta
Deal found 7/29![Delta logo]()
$366
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:45 am
SJC
- MDW
2 stops7h 15m
Southwest
Thu 9/247:10 am
MDW
- SJC
2 stops7h 40m
Southwest
Deal found 7/30![Southwest logo]()
$333
This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:25 pm
SJC
- ORD
1 stop7h 34m
Alaska Airlines
Mon 9/76:01 am
ORD
- SJC
1 stop18h 55m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:30 am
SJC
- ORD
Nonstop4h 25m
United Airlines
Sun 9/135:55 am
ORD
- SJC
1 stop9h 09m
United Airlines
Deal found 7/28![United Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 7/31. 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 9/56:30 am
SJC
- MDW
1 stop7h 35m
Southwest
Fri 9/115:00 pm
MDW
- SJC
2 stops7h 20m
Southwest
Deal found 7/31![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/212:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Wed 9/237:00 am
ORD
- SJC
1 stop8h 08m
United Airlines
Deal found 7/27![United Airlines logo]()
$387
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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 8/195:06 pm
SJC
- ORD
1 stop18h 16m
Alaska Airlines
Tue 8/256:01 am
ORD
- SJC
1 stop6h 58m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Sun 10/42:08 pm
SJC
- ORD
Nonstop4h 27m
United Airlines
Tue 10/278:12 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 8/1![United Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:55 am
SJC
- MDW
2 stops7h 15m
Southwest
Mon 8/245:00 pm
MDW
- SJC
2 stops7h 15m
Southwest
Deal found 7/27![Southwest logo]()
$377
This Alaska Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:45 pm
SJC
- ORD
1 stop9h 35m
Alaska Airlines
Tue 8/186:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$421
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:45 am
SJC
- ORD
1 stop8h 55m
United Airlines
Thu 9/247:55 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/30![United Airlines logo]()
$403
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2211:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Wed 12/305:55 am
MDW
- SJC
1 stop6h 20m
Southwest
Deal found 7/28![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 7/31. 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 9/26:50 am
SJC
- MDW
1 stop7h 45m
Southwest
Wed 9/98:30 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 7/31![Southwest logo]()
$379
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Tue 9/88:59 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 7/29![United Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:03 pm
SJC
- RFD
1 stop19h 44m
Multiple Airlines
Sat 11/281:32 pm
RFD
- SJC
1 stop21h 04m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$730
This Southwest deal was found by Cheapflights users on 7/31. 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 8/2911:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Tue 9/12:05 pm
MDW
- SJC
2 stops8h 15m
Southwest
Deal found 7/31![Southwest logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/231:48 pm
SJC
- RFD
2 stops19h 49m
Multiple Airlines
Thu 12/3112:27 pm
RFD
- SJC
1 stop24h 36m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$754
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:23 pm
SJC
- RFD
2 stops19h 13m
Multiple Airlines
Sun 8/161:24 pm
RFD
- SJC
1 stop25h 53m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$758
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2611:58 am
SJC
- RFD
1 stop21h 39m
Multiple Airlines
Sat 1/27:45 pm
RFD
- SJC
2 stops17h 18m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$904
Last-minute flights from San Jose to ChicagoDiscover last-minute flight deals from San Jose to Chicago. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Chicago. Data last updated August 1, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/183:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Fri 8/282:18 pm
ORD
- SJC
1 stop6h 51m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:45 am
SJC
- MDW
2 stops7h 15m
Southwest
Tue 8/185:15 pm
MDW
- SJC
1 stop6h 20m
Southwest
Deal found 7/28![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Tue 8/258:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/28![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Tue 8/258:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/28![United Airlines logo]()
$315
This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:29 am
SJC
- ORD
1 stop9h 52m
Alaska Airlines
Wed 8/262:18 pm
ORD
- SJC
1 stop6h 51m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:14 pm
SJC
- ORD
1 stop8h 03m
Frontier
Thu 8/272:41 pm
ORD
- SJC
2 stops30h 38m
Frontier
Deal found 7/28![Frontier logo]()
$324
This Alaska Airlines deal was found by Cheapflights users on 8/1. 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 8/247:29 am
SJC
- ORD
1 stop9h 52m
Alaska Airlines
Sat 8/296:01 am
ORD
- SJC
1 stop14h 03m
Alaska Airlines
Deal found 8/1![Alaska Airlines logo]()
$326
This Alaska Airlines deal was found by Cheapflights users on 8/1. 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 8/248:29 am
SJC
- ORD
1 stop8h 52m
Alaska Airlines
Thu 8/272:18 pm
ORD
- SJC
1 stop6h 51m
Alaska Airlines
Deal found 8/1![Alaska Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Sun 8/308:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/30![United Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Sat 8/296:20 am
SJC
- ORD
Nonstop4h 25m
United Airlines
Sat 9/56:00 am
ORD
- SJC
1 stop9h 08m
United Airlines
Deal found 8/1![United Airlines logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 8/1. 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.
Sat 8/2910:12 am
SJC
- ORD
1 stop7h 09m
Alaska Airlines
Tue 9/16:01 am
ORD
- SJC
1 stop6h 58m
Alaska Airlines
Deal found 8/1![Alaska Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:10 am
SJC
- MDW
Nonstop4h 10m
Southwest
Mon 8/318:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/30![Southwest logo]()
$327
One-way flights from San Jose to ChicagoSearch for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
Search for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:51 pm
SJC
- MDW
1 stop7h 53m
Delta
Deal found 7/29![Delta logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:03 pm
SJC
- ORD
2 stops25h 20m
Frontier
Deal found 7/28![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:03 pm
SJC
- MDW
2 stops24h 41m
Frontier
Deal found 7/27![Frontier logo]()
$162
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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 9/28:29 am
SJC
- ORD
1 stop8h 52m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:03 pm
SJC
- MDW
2 stops24h 41m
Frontier
Deal found 7/30![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:14 pm
SJC
- ORD
1 stop7h 45m
Frontier
Deal found 7/30![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:14 pm
SJC
- MDW
2 stops22h 17m
Frontier
Deal found 7/30![Frontier logo]()
$164
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:30 am
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/28![United Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:03 pm
SJC
- MDW
2 stops24h 41m
Frontier
Deal found 7/27![Frontier logo]()
$165
This Priceline deal was found by Cheapflights users on 7/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:29 am
SJC
- ORD
1 stop8h 52m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:17 pm
SJC
- MDW
2 stops18h 38m
Frontier
Deal found 7/27![Frontier logo]()
$167
This Alaska Airlines deal was found by Cheapflights users on 8/1. 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 9/78:17 pm
SJC
- ORD
1 stop21h 04m
Alaska Airlines
Deal found 8/1![Alaska Airlines logo]()
$167
Find flight deals from San Jose to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $313 (United Airlines) |
One-way from | $160 (Delta) |
Popular in | December |
Cheapest in | February |
Average price | $422 |
Good round-trip deal | $377 or less |
Good one-way deal | $223 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose 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 August 1, 2026.
Use the filters below to find and compare flights from San Jose to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 8/21
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Tue 8/25
6:50 am-11:20 am
1 stop6h 30m
$325
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 8/28
8:15 am-5:00 pm
1 stop6h 45m
Chicago Midway
Tue 9/1
8:30 pm-11:00 pm
Nonstop4h 30m
$325
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 10/1
8:40 am-5:50 pm
2 stops7h 10m
Chicago Midway
Mon 10/5
6:15 pm-11:55 pm
1 stop7h 40m
$328
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 9/22
6:45 am-4:00 pm
2 stops7h 15m
Chicago Midway
Thu 9/24
7:10 am-12:50 pm
2 stops7h 40m
$333
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 8/21
10:20 pm-10:10 am
1 stop9h 50m
Chicago Midway
Tue 9/1
1:51 pm-8:24 pm
1 stop8h 33m
$335
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 8/26
12:37 pm-10:36 pm
1 stop7h 59m
Chicago Midway
Fri 8/28
6:05 am-11:22 am
1 stop7h 17m
$335
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 8/27
2:10 pm-8:35 pm
Nonstop4h 25m
Chicago O'Hare Intl
Mon 8/31
8:03 pm-10:50 pm
Nonstop4h 47m
$337
San JoseChicago
SJC - ORD
SJCORD
San Jose
Sun 9/27
2:08 pm-8:35 pm
Nonstop4h 27m
Chicago O'Hare Intl
Wed 9/30
9:14 am-12:01 pm
Nonstop4h 47m
$337
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sat 9/5
6:30 am-4:05 pm
1 stop7h 35m
Chicago Midway
Fri 9/11
5:00 pm-10:20 pm
2 stops7h 20m
$342
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 8/12
10:03 am-6:57 pm
1 stop6h 54m
Chicago O'Hare Intl
Tue 8/18
2:20 pm-7:11 pm
1 stop6h 51m
$362
Showing 1-10 of 59 resultsSorted by cheapest first
Compare providers for flights from San Jose to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Jose to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Jose, California-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose, California-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose, California-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Jose, California-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Jose, California-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from San Jose to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Jose with our price prediction graph.
SJC-CHI
SJC-MDW
SJC-ORD
SJC-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Jose to Chicago
SJC-CHI
SJC-MDW
SJC-ORD
SJC-RFD
What is the cheapest month to book a flight from San Jose, California to Chicago?
Currently, April is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $405). Flying from San Jose, California to Chicago in June is currently the most expensive (average of $577). 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 SJC to CHI?
Find hourly flight availability from San Jose 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 August 1, 2026.
A simple way to save on the total cost of your ticket is to fly from San Jose, California to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 19% on your trip compared to booking a flight at noon.
How much does it cost to fly round-trip from San Jose, California to Chicago?
Airfare is below average for this route at the moment.
San Jose, California to Chicago flights typically cost between $346 and $518 in August.The cheapest round-trip price found within the last 5 days was $313 on United Airlines (Aug 29-Sep 5).
How far ahead should I book a flight from San Jose, California to Chicago?
The best time to book flights from San Jose, California to Chicago is 67 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
The best insider tips for San Jose to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your San Jose to Chicago trip
Our travel experts
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 August 1, 2026.
Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andDelta from San Jose to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San Jose 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 locationsBenton Harbor
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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 August 1, 2026.
Complete your trip
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San Jose and Chicago flights
Browse other San Jose and Chicago flight options. Last updated on August 1, 2026.
Other flights from San Jose
Browse through other flights departing from San Jose. Flights are based on user searches made on Cheapflights and were last updated on August 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from San Jose to Chicago
Discover the top 6 airlines that operate flights from San Jose 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 August 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$131 | Average$490 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$490 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$236 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$342 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$270 | Average$521 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$280 | Average$564 | FlexibilityNo cancel fee | On-time69% |