$150+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Aug 3 — Aug 101
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
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 July 4, 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 July 4, 2026.
This Southwest deal was found by Cheapflights users on 6/29. 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.
Sat 9/127:10 am
SJC
- MDW
Nonstop4h 05m
Southwest
Fri 9/186:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 6/29![Southwest logo]()
$328
This Frontier deal was found by Cheapflights users on 6/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:24 pm
SJC
- ORD
1 stop13h 18m
Frontier
Thu 10/16:50 am
ORD
- SJC
1 stop8h 39m
Frontier
Deal found 6/29![Frontier logo]()
$328
This Southwest deal was found by Cheapflights users on 6/30. 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.
Sat 9/511:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Tue 9/88:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 6/30![Southwest logo]()
$329
This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:23 pm
SJC
- ORD
1 stop7h 54m
Multiple Airlines
Tue 7/212:20 pm
ORD
- SJC
1 stop6h 51m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$329
This Trip.com deal was found by Cheapflights users on 6/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:13 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Fri 8/216:01 am
ORD
- SJC
1 stop9h 44m
Alaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/38:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Sat 8/87:29 am
ORD
- SJC
2 stops13h 59m
Frontier
Deal found 7/2![Frontier logo]()
$331
This Southwest deal was found by Cheapflights users on 6/30. 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 7/288:55 pm
SJC
- MDW
1 stop6h 30m
Southwest
Thu 7/308:50 pm
MDW
- SJC
Nonstop4h 40m
Southwest
Deal found 6/30![Southwest logo]()
$332
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/72:32 pm
SJC
- ORD
1 stop8h 12m
United Airlines
Sat 8/158:59 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 7/1![United Airlines logo]()
$332
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2310:12 am
SJC
- ORD
1 stop7h 09m
Alaska Airlines
Mon 8/246:01 am
ORD
- SJC
1 stop6h 58m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$333
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/243:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Tue 7/286:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Wed 8/192:41 pm
ORD
- SJC
2 stops30h 38m
Frontier
Deal found 7/1![Frontier logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Tue 9/299:03 pm
SJC
- ORD
2 stops34h 58m
Frontier
Mon 10/56:50 am
ORD
- SJC
1 stop8h 39m
Frontier
Deal found 6/29![Frontier logo]()
$336
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 July 4, 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 July 4, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:29 am
SJC
- ORD
1 stop8h 52m
Alaska Airlines
Sun 8/306:01 am
ORD
- SJC
1 stop6h 58m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$333
This United Airlines deal was found by Cheapflights users on 6/29. 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
Wed 9/99:00 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 6/29![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 6/29. 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 10/212:46 pm
SJC
- MDW
1 stop7h 59m
Delta
Tue 10/61:00 pm
MDW
- SJC
1 stop10h 25m
Delta
Deal found 6/29![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:35 pm
SJC
- MDW
1 stop7h 05m
Southwest
Sat 8/15:10 pm
MDW
- SJC
1 stop7h 45m
Southwest
Deal found 7/2![Southwest logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 10/152:24 pm
SJC
- RFD
2 stops19h 03m
Multiple Airlines
Sun 10/189:33 pm
RFD
- SJC
1 stop17h 56m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$421
This United Airlines deal was found by Cheapflights users on 6/30. 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 10/206:30 am
SJC
- ORD
Nonstop4h 22m
United Airlines
Wed 10/217:55 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 6/30![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:35 pm
SJC
- MDW
1 stop8h 01m
Delta
Tue 9/11:51 pm
MDW
- SJC
1 stop8h 33m
Delta
Deal found 7/2![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/811:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Sat 8/152:05 pm
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 7/3![Southwest logo]()
$365
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/239:09 am
SJC
- ORD
1 stop7h 48m
Alaska Airlines
Tue 7/286:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:30 pm
SJC
- MDW
1 stop7h 10m
Southwest
Mon 8/178:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/3![Southwest logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:10 am
SJC
- RFD
1 stop9h 29m
Multiple Airlines
Mon 9/148:44 pm
RFD
- SJC
2 stops25h 24m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 7/1. 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.
Fri 8/218:29 am
SJC
- ORD
1 stop8h 52m
Alaska Airlines
Tue 9/12:22 pm
ORD
- SJC
2 stops10h 34m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 6/29. 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 8/122:59 pm
SJC
- MDW
2 stops17h 00m
Delta
Mon 8/175:10 pm
MDW
- SJC
1 stop7h 48m
Delta
Deal found 6/29![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Tue 9/88:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/2![United Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 6/30. 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 10/16:15 am
SJC
- MDW
2 stops7h 00m
Southwest
Mon 10/55:20 pm
MDW
- SJC
1 stop7h 10m
Southwest
Deal found 6/30![Southwest logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 9/109:10 am
SJC
- RFD
1 stop9h 29m
Multiple Airlines
Thu 9/179:29 pm
RFD
- SJC
1 stop18h 00m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Fri 8/212:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Tue 9/14:20 pm
ORD
- SJC
1 stop6h 37m
United Airlines
Deal found 6/29![United Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Tue 10/64:35 pm
MDW
- SJC
1 stop6h 50m
Southwest
Deal found 7/3![Southwest logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 10/19:10 am
SJC
- RFD
1 stop9h 03m
Multiple Airlines
Thu 10/298:20 pm
RFD
- SJC
1 stop19h 09m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$458
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:10 am
SJC
- MDW
Nonstop4h 05m
Southwest
Sun 8/308:40 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/3![Southwest logo]()
$393
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:32 pm
SJC
- ORD
1 stop6h 47m
United Airlines
Fri 8/77:58 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 7/1![United Airlines logo]()
$450
This Southwest deal was found by Cheapflights users on 6/29. 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.
Sat 8/89:55 am
SJC
- MDW
2 stops7h 35m
Southwest
Tue 8/112:05 pm
MDW
- SJC
2 stops8h 15m
Southwest
Deal found 6/29![Southwest logo]()
$394
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:51 pm
SJC
- ORD
1 stop9h 08m
United Airlines
Tue 8/189:00 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 7/3![United Airlines logo]()
$454
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Sun 9/279:10 am
SJC
- RFD
1 stop9h 29m
Multiple Airlines
Sun 10/49:36 pm
RFD
- SJC
1 stop17h 53m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$506
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:55 pm
SJC
- MDW
1 stop7h 35m
Southwest
Tue 8/182:05 pm
MDW
- SJC
2 stops8h 15m
Southwest
Deal found 7/3![Southwest logo]()
$404
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Mon 8/318:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/3![United Airlines logo]()
$483
Last-minute flights from San Jose to ChicagoDiscover last-minute flight deals from San Jose to Chicago. Data last updated July 4, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Chicago. Data last updated July 4, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:23 pm
SJC
- ORD
1 stop7h 54m
Multiple Airlines
Tue 7/212:20 pm
ORD
- SJC
1 stop6h 51m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$329
This Alaska Airlines deal was found by Cheapflights users on 6/30. 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.
Fri 7/247:13 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Wed 7/296:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 6/30. 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 7/288:55 pm
SJC
- MDW
1 stop6h 30m
Southwest
Thu 7/308:50 pm
MDW
- SJC
Nonstop4h 40m
Southwest
Deal found 6/30![Southwest logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/38:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Sat 8/87:29 am
ORD
- SJC
2 stops13h 59m
Frontier
Deal found 7/2![Frontier logo]()
$331
This Expedia deal was found by Cheapflights users on 6/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/62:12 pm
SJC
- ORD
1 stop13h 25m
Frontier
Sun 8/99:13 pm
ORD
- SJC
1 stop24h 15m
Frontier
Deal found 6/29![Frontier logo]()
$328
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/72:32 pm
SJC
- ORD
1 stop8h 12m
United Airlines
Sat 8/158:59 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 7/1![United Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:55 pm
SJC
- MDW
1 stop7h 35m
Southwest
Sat 8/152:05 pm
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 7/1![Southwest logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 8/88:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Tue 8/115:30 pm
ORD
- SJC
2 stops45h 47m
Frontier
Deal found 6/29![Frontier logo]()
$336
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Wed 8/198:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/1![United Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Wed 8/192:41 pm
ORD
- SJC
2 stops30h 38m
Frontier
Deal found 7/1![Frontier logo]()
$335
This Trip.com deal was found by Cheapflights users on 6/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:13 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Fri 8/216:01 am
ORD
- SJC
1 stop9h 44m
Alaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$330
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:29 am
SJC
- ORD
1 stop9h 52m
Alaska Airlines
Thu 8/276:01 am
ORD
- SJC
1 stop6h 58m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$333
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 July 4, 2026.
Search for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Data last updated July 4, 2026.
This Expedia deal was found by Cheapflights users on 6/30. 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 Expedia 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 6/30![Frontier logo]()
$150
This Super.com deal was found by Cheapflights users on 7/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 7/1![Frontier logo]()
$151
This Super.com deal was found by Cheapflights users on 6/29. 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 Super.com 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 6/29![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Mon 8/318:14 pm
SJC
- ORD
2 stops39h 22m
Frontier
Deal found 6/30![Frontier logo]()
$158
This Expedia deal was found by Cheapflights users on 6/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/302:12 pm
SJC
- ORD
1 stop13h 25m
Frontier
Deal found 6/30![Frontier logo]()
$160
This United Airlines deal was found by Cheapflights users on 6/29. 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 7/221:10 pm
SJC
- ORD
1 stop9h 35m
United Airlines
Deal found 6/29![United Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:03 pm
SJC
- MDW
2 stops22h 55m
Frontier
Deal found 7/2![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/18:23 pm
SJC
- MDW
2 stops22h 09m
Frontier
Deal found 7/3![Frontier logo]()
$163
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 7/1![Southwest logo]()
$165
This United Airlines deal was found by Cheapflights users on 7/1. 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 8/152:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/1![United Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:14 pm
SJC
- ORD
1 stop8h 03m
Frontier
Deal found 7/2![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 8/158:23 pm
SJC
- MDW
2 stops22h 09m
Frontier
Deal found 6/29![Frontier 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 July 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $328 (Southwest) |
One-way from | $150 (Expedia) |
Popular in | December |
Cheapest in | September |
Average price | $502 |
Good round-trip deal | $472 or less |
Good one-way deal | $236 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 July 4, 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
Sat 8/22
8:29 am-7:21 pm
1 stop8h 52m
Chicago O'Hare Intl
Sun 8/30
6:01 am-10:59 am
1 stop6h 58m
$333
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 9/2
2:10 pm-8:35 pm
Nonstop4h 25m
Chicago O'Hare Intl
Wed 9/9
9:00 am-11:46 am
Nonstop4h 46m
$337
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 10/20
6:30 am-12:52 pm
Nonstop4h 22m
Chicago O'Hare Intl
Wed 10/21
7:55 pm-10:42 pm
Nonstop4h 47m
$337
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 10/2
12:46 pm-10:45 pm
1 stop7h 59m
Chicago Midway
Tue 10/6
1:00 pm-9:25 pm
1 stop10h 25m
$342
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 8/21
12:35 pm-10:36 pm
1 stop8h 01m
Chicago Midway
Tue 9/1
1:51 pm-8:24 pm
1 stop8h 33m
$342
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 7/28
7:35 pm-4:40 am
1 stop7h 05m
Chicago Midway
Sat 8/1
5:10 pm-10:55 pm
1 stop7h 45m
$362
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sat 8/8
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Sat 8/15
2:05 pm-6:15 pm
1 stop6h 10m
$365
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 8/13
8:30 pm-5:40 am
1 stop7h 10m
Chicago Midway
Mon 8/17
8:50 pm-11:20 pm
Nonstop4h 30m
$369
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 10/1
6:15 am-3:15 pm
2 stops7h 00m
Chicago Midway
Mon 10/5
5:20 pm-10:30 pm
1 stop7h 10m
$384
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 7/23
9:09 am-6:57 pm
1 stop7h 48m
Chicago O'Hare Intl
Tue 7/28
6:20 am-11:24 am
1 stop7h 04m
$387
Showing 1-10 of 55 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 July.
| 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 July 4, 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 18% on your trip compared to booking a flight in the evening.
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 July 4, 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.
Food
7.1
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Dec 2025
SJC - SEA
Food
7.1
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Dec 2025
SJC - SEA
Food
7.1
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Dec 2025
SJC - SEA
Food
7.1
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Dec 2025
SJC - SEA
Food
7.1
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Dec 2025
SJC - SEA
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
Hammond
Lansing
Merrillville
Valparaiso
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from San Jose
Popular flights
Alternative routes for San Jose to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 4, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San Jose to Chicago by cabin class
Find flights from San Jose to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Jose and Chicago flights
Browse other San Jose and Chicago flight options. Last updated on July 4, 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 July 4, 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 July 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$157 | Average$490 | 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$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$270 | Average$525 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$294 | Average$563 | FlexibilityNo cancel fee | On-time69% |