$144+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Jul 21 — Jul 281
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 September or February, 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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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 June 21, 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 June 21, 2026.
This Booking.com deal was found by Cheapflights users on 6/17. 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 Booking.com 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
Multiple Airlines
Sun 8/239:07 pm
ORD
- SJC
1 stop16h 55m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$332
This Expedia deal was found by Cheapflights users on 6/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:23 pm
SJC
- ORD
1 stop7h 54m
Multiple Airlines
Mon 7/137:59 pm
ORD
- SJC
1 stop15h 27m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$333
This Alaska Airlines deal was found by Cheapflights users on 6/17. 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 7/227:13 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Fri 7/246:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/17![Alaska Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 6/19. 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 8/2611:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Sat 8/292:05 pm
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 6/19![Southwest logo]()
$335
This Alaska Airlines deal was found by Cheapflights users on 6/19. 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.
Fri 8/143:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Thu 8/206:01 am
ORD
- SJC
1 stop6h 58m
Alaska Airlines
Deal found 6/19![Alaska Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Mon 8/108:23 pm
SJC
- ORD
2 stops22h 29m
Frontier
Wed 8/199:20 pm
ORD
- SJC
1 stop24h 08m
Frontier
Deal found 6/19![Frontier logo]()
$337
This Frontier deal was found by Cheapflights users on 6/20. 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 7/162:12 pm
SJC
- ORD
1 stop13h 25m
Frontier
Fri 7/247:15 am
ORD
- SJC
1 stop8h 02m
Frontier
Deal found 6/20![Frontier logo]()
$338
This Southwest deal was found by Cheapflights users on 6/19. 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 7/228:55 pm
SJC
- MDW
1 stop6h 30m
Southwest
Sat 7/258:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 6/19![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 6/19. 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 8/511:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Wed 8/122:05 pm
MDW
- SJC
2 stops8h 15m
Southwest
Deal found 6/19![Southwest logo]()
$340
This Booking.com deal was found by Cheapflights users on 6/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:12 pm
SJC
- ORD
1 stop13h 25m
Multiple Airlines
Sat 7/116:20 am
ORD
- SJC
1 stop7h 04m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$340
This Expedia deal was found by Cheapflights users on 6/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:00 am
SJC
- ORD
1 stop19h 00m
Alaska Airlines
Tue 8/117:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$341
This Frontier deal was found by Cheapflights users on 6/19. 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.
Fri 7/102:12 pm
SJC
- ORD
1 stop13h 25m
Frontier
Mon 7/137:15 am
ORD
- SJC
1 stop8h 02m
Frontier
Deal found 6/19![Frontier logo]()
$343
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 June 21, 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 June 21, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/17. 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.
Sun 10/255:18 pm
SJC
- ORD
1 stop18h 07m
Alaska Airlines
Thu 10/292:21 pm
ORD
- SJC
1 stop10h 30m
Alaska Airlines
Deal found 6/17![Alaska Airlines logo]()
$347
This United Airlines deal was found by Cheapflights users on 6/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:20 am
SJC
- ORD
Nonstop4h 25m
United Airlines
Mon 8/242:42 pm
ORD
- SJC
1 stop8h 15m
United Airlines
Deal found 6/20![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 6/19. 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.
Sat 7/1810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sat 7/2512:20 pm
MDW
- SJC
2 stops7h 35m
Southwest
Deal found 6/19![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 6/20. 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.
Tue 9/298:53 pm
SJC
- MDW
2 stops9h 55m
Delta
Fri 10/210:48 am
MDW
- SJC
1 stop10h 09m
Delta
Deal found 6/20![Delta logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/139:10 am
SJC
- RFD
1 stop9h 29m
Multiple Airlines
Sun 9/209:29 pm
RFD
- SJC
1 stop18h 00m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$395
This United Airlines deal was found by Cheapflights users on 6/16. 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 8/46:30 am
SJC
- ORD
Nonstop4h 24m
United Airlines
Thu 8/67:58 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 6/16![United Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 6/18. 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 8/2511:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Thu 8/276:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 6/18![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 6/20. 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.
Fri 8/2112:35 pm
SJC
- MDW
1 stop8h 01m
Delta
Tue 9/19:59 am
MDW
- SJC
2 stops8h 07m
Delta
Deal found 6/20![Delta logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:10 am
SJC
- RFD
1 stop9h 29m
Multiple Airlines
Mon 9/218:44 pm
RFD
- SJC
2 stops25h 24m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$398
This Alaska Airlines deal was found by Cheapflights users on 6/20. 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.
Tue 9/226:46 pm
SJC
- ORD
2 stops9h 34m
Alaska Airlines
Wed 9/232:18 pm
ORD
- SJC
1 stop6h 51m
Alaska Airlines
Deal found 6/20![Alaska Airlines logo]()
$398
This Delta deal was found by Cheapflights users on 6/20. 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.
Fri 8/146:12 pm
SJC
- MDW
2 stops13h 05m
Delta
Tue 8/181:25 pm
MDW
- SJC
2 stops10h 48m
Delta
Deal found 6/20![Delta logo]()
$398
This Southwest deal was found by Cheapflights users on 6/17. 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.
Thu 8/1311:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Mon 8/178:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 6/17![Southwest logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 6/17. 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.
Tue 7/145:02 pm
SJC
- ORD
1 stop18h 19m
Alaska Airlines
Sun 7/196:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/17![Alaska Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 6/19. 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.
Thu 9/312:51 pm
SJC
- ORD
1 stop9h 08m
United Airlines
Tue 9/88:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 6/19![United Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Sat 8/152:12 pm
SJC
- RFD
1 stop20h 22m
Multiple Airlines
Thu 8/209:35 pm
RFD
- SJC
1 stop17h 47m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 6/20. 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.
Mon 8/242:59 pm
SJC
- ORD
1 stop6h 49m
Delta
Sun 9/206:00 am
ORD
- SJC
2 stops10h 14m
Delta
Deal found 6/20![Delta logo]()
$410
This Southwest deal was found by Cheapflights users on 6/18. 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.
Sun 9/133:20 pm
SJC
- MDW
2 stops7h 35m
Southwest
Sun 9/207:10 am
MDW
- SJC
1 stop8h 05m
Southwest
Deal found 6/18![Southwest logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Sat 8/152:12 pm
SJC
- RFD
1 stop20h 22m
Multiple Airlines
Wed 8/192:13 pm
RFD
- SJC
2 stops23h 54m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$441
This United Airlines deal was found by Cheapflights users on 6/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Sat 8/298:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 6/20![United Airlines logo]()
$446
This Delta deal was found by Cheapflights users on 6/19. 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.
Thu 8/67:05 am
SJC
- ORD
2 stops12h 25m
Delta
Fri 8/147:48 am
ORD
- SJC
2 stops11h 24m
Delta
Deal found 6/19![Delta logo]()
$415
This Southwest deal was found by Cheapflights users on 6/16. 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.
Sun 12/1310:00 am
SJC
- MDW
2 stops8h 05m
Southwest
Mon 12/145:45 am
MDW
- SJC
2 stops8h 20m
Southwest
Deal found 6/16![Southwest logo]()
$429
This Delta deal was found by Cheapflights users on 6/18. 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 9/56:10 am
SJC
- MDW
1 stop7h 47m
Delta
Sat 9/126:05 am
MDW
- SJC
1 stop7h 31m
Delta
Deal found 6/18![Delta logo]()
$419
This Southwest deal was found by Cheapflights users on 6/16. 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 10/1511:45 am
SJC
- MDW
Nonstop4h 05m
Southwest
Sun 10/1810:10 am
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 6/16![Southwest logo]()
$445
This Delta deal was found by Cheapflights users on 6/19. 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.
Mon 7/208:25 pm
SJC
- ORD
2 stops10h 05m
Delta
Sat 7/257:29 am
ORD
- SJC
1 stop8h 43m
Delta
Deal found 6/19![Delta logo]()
$432
This Southwest deal was found by Cheapflights users on 6/19. 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.
Fri 9/187:50 am
SJC
- MDW
1 stop6h 50m
Southwest
Fri 9/186:15 pm
MDW
- SJC
1 stop6h 50m
Southwest
Deal found 6/19![Southwest logo]()
$447
This Southwest deal was found by Cheapflights users on 6/17. 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.
Fri 11/138:30 am
SJC
- MDW
2 stops7h 15m
Southwest
Sun 11/154:45 pm
MDW
- SJC
1 stop6h 25m
Southwest
Deal found 6/17![Southwest logo]()
$448
Last-minute flights from San Jose to ChicagoDiscover last-minute flight deals from San Jose to Chicago. Data last updated June 21, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Chicago. Data last updated June 21, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 6/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:12 pm
SJC
- ORD
1 stop13h 25m
Multiple Airlines
Sat 7/116:20 am
ORD
- SJC
1 stop7h 04m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$340
This Expedia deal was found by Cheapflights users on 6/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:12 pm
SJC
- ORD
1 stop13h 25m
Multiple Airlines
Tue 7/146:20 am
ORD
- SJC
1 stop7h 04m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$345
This Expedia deal was found by Cheapflights users on 6/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:12 pm
SJC
- ORD
1 stop13h 25m
Frontier
Mon 7/137:15 am
ORD
- SJC
1 stop8h 02m
Frontier
Deal found 6/19![Frontier logo]()
$349
This Expedia deal was found by Cheapflights users on 6/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:23 pm
SJC
- ORD
1 stop7h 54m
Multiple Airlines
Mon 7/137:59 pm
ORD
- SJC
1 stop15h 27m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$333
This Frontier deal was found by Cheapflights users on 6/19. 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.
Fri 7/102:12 pm
SJC
- ORD
1 stop13h 25m
Frontier
Mon 7/137:15 am
ORD
- SJC
1 stop8h 02m
Frontier
Deal found 6/19![Frontier logo]()
$343
This Alaska Airlines deal was found by Cheapflights users on 6/20. 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.
Mon 7/133:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Wed 7/226:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/20![Alaska Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 6/20. 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 7/1410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 7/215:25 am
MDW
- SJC
2 stops8h 00m
Southwest
Deal found 6/20![Southwest logo]()
$344
This Frontier deal was found by Cheapflights users on 6/20. 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 7/162:12 pm
SJC
- ORD
1 stop13h 25m
Frontier
Fri 7/247:15 am
ORD
- SJC
1 stop8h 02m
Frontier
Deal found 6/20![Frontier logo]()
$338
This Alaska Airlines deal was found by Cheapflights users on 6/17. 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 7/227:13 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Fri 7/246:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/17![Alaska Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 6/19. 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 7/228:55 pm
SJC
- MDW
1 stop6h 30m
Southwest
Sat 7/258:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 6/19![Southwest logo]()
$339
This Alaska Airlines deal was found by Cheapflights users on 6/17. 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 7/256:47 pm
SJC
- ORD
1 stop8h 13m
Alaska Airlines
Wed 8/56:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/17![Alaska Airlines logo]()
$344
This Expedia deal was found by Cheapflights users on 6/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:00 am
SJC
- ORD
1 stop19h 00m
Alaska Airlines
Tue 8/117:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$341
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 June 21, 2026.
Search for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Data last updated June 21, 2026.
This Frontier deal was found by Cheapflights users on 6/20. 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.
Mon 7/208:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 6/20![Frontier logo]()
$144
This Alaska Airlines deal was found by Cheapflights users on 6/19. 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.
Tue 7/143:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Deal found 6/19![Alaska Airlines logo]()
$145
This Frontier deal was found by Cheapflights users on 6/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:24 pm
SJC
- ORD
1 stop13h 18m
Frontier
Deal found 6/18![Frontier logo]()
$146
This Expedia deal was found by Cheapflights users on 6/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:12 pm
SJC
- ORD
1 stop15h 09m
Alaska Airlines
Deal found 6/20![Alaska Airlines logo]()
$150
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 6/17![Frontier logo]()
$151
This Super.com deal was found by Cheapflights users on 6/20. 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.
Fri 7/178:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 6/20![Frontier logo]()
$152
This Frontier deal was found by Cheapflights users on 6/20. 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 7/168:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 6/20![Frontier logo]()
$154
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:02 pm
SJC
- ORD
1 stop28h 00m
Frontier
Deal found 6/17![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Fri 7/38:25 pm
SJC
- ORD
1 stop31h 54m
Frontier
Deal found 6/17![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:03 pm
SJC
- MDW
2 stops22h 55m
Frontier
Deal found 6/21![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 6/19. 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 8/132:12 pm
SJC
- ORD
1 stop13h 25m
Frontier
Deal found 6/19![Frontier logo]()
$160
This Alaska Airlines deal was found by Cheapflights users on 6/17. 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 9/210:12 am
SJC
- ORD
1 stop7h 09m
Alaska Airlines
Deal found 6/17![Alaska Airlines logo]()
$161
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 June 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $332 (Booking.com) |
One-way from | $144 (Frontier) |
Popular in | December |
Cheapest in | September |
Average price | $472 |
Good round-trip deal | $472 or less |
Good one-way deal | $226 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 June 21, 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 - ORD
SJCORD
San Jose
Sun 10/25
5:18 pm-1:25 pm
1 stop18h 07m
Chicago O'Hare Intl
Thu 10/29
2:21 pm-10:51 pm
1 stop10h 30m
$347
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 8/13
6:20 am-12:45 pm
Nonstop4h 25m
Chicago O'Hare Intl
Mon 8/24
2:42 pm-8:57 pm
1 stop8h 15m
$373
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sat 7/18
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Sat 7/25
12:20 pm-5:55 pm
2 stops7h 35m
$379
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 8/4
6:30 am-12:54 pm
Nonstop4h 24m
Chicago O'Hare Intl
Thu 8/6
7:58 pm-10:43 pm
Nonstop4h 45m
$380
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 8/25
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Thu 8/27
6:15 am-10:30 am
1 stop6h 15m
$386
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 9/29
8:53 pm-8:48 am
2 stops9h 55m
Chicago Midway
Fri 10/2
10:48 am-6:57 pm
1 stop10h 09m
$393
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 8/21
12:35 pm-10:36 pm
1 stop8h 01m
Chicago Midway
Tue 9/1
9:59 am-4:06 pm
2 stops8h 07m
$393
San JoseChicago
SJC - RFD
SJCRFD
San Jose
Sun 9/13
9:10 am-8:39 pm
1 stop9h 29m
Chicago Greater Rockford
Sun 9/20
9:29 pm-1:29 pm
1 stop18h 00m
$395
San JoseChicago
SJC - RFD
SJCRFD
San Jose
Thu 9/17
9:10 am-8:39 pm
1 stop9h 29m
Chicago Greater Rockford
Mon 9/21
8:44 pm-8:08 pm
2 stops25h 24m
$398
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 9/22
6:46 pm-6:20 am
2 stops9h 34m
Chicago O'Hare Intl
Wed 9/23
2:18 pm-7:09 pm
1 stop6h 51m
$398
Showing 1-10 of 56 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 June.
| 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-ORD
SJC-MDW
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-ORD
SJC-MDW
SJC-RFD
What is the cheapest month to book a flight from San Jose, California to Chicago?
Currently, March is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $95). Flying from San Jose, California to Chicago in April is currently the most expensive (average of $265). 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 June 21, 2026.
A simple way to save on the total cost of your ticket is to fly from San Jose, California to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight in the evening.
Weekly flight availability from San Jose, California to Chicago
Explore weekly flight availability from San Jose 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 June 21, 2026.
The most flights from SJC to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from San Jose, California to Chicago?
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 78 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 June 21, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Southwest, 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
7.8
Crew
8.5
Food
7.0
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Crew
8.5
Food
7.0
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Crew
8.5
Food
7.0
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Crew
8.5
Food
7.0
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Crew
8.5
Food
7.0
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
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 June 21, 2026.
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San Jose and Chicago flights
Browse other San Jose and Chicago flight options. Last updated on June 21, 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 June 21, 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 June 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$131 | Average$337 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$346 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$236 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$253 | Average$424 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$270 | Average$519 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$294 | Average$564 | FlexibilityNo cancel fee | On-time69% |