$142+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Jul 6 — Jul 131
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 February or September, booked 80 days in advance, depart on a Wednesday or Saturday and return on a Wednesday
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 June 6, 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 6, 2026.
This Expedia deal was found by Cheapflights users on 6/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:37 pm
SJC
- ORD
1 stop8h 23m
Alaska Airlines
Tue 7/147:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$313
This SmartFares deal was found by Cheapflights users on 6/1. 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 SmartFares 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 8/46:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$314
This Alaska Airlines deal was found by Cheapflights users on 6/2. 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 8/16:37 pm
SJC
- ORD
1 stop8h 23m
Alaska Airlines
Thu 8/66:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/2![Alaska Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Thu 8/205:55 am
ORD
- SJC
1 stop9h 13m
United Airlines
Deal found 6/2![United Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 6/1. 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 6/234:00 pm
SJC
- ORD
1 stop6h 44m
United Airlines
Tue 6/306:30 am
ORD
- SJC
1 stop7h 33m
United Airlines
Deal found 6/1![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 6/2. 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 7/1410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 7/218:55 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 6/2![Southwest logo]()
$330
This Alaska Airlines deal was found by Cheapflights users on 6/3. 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.
Tue 6/303:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Fri 7/102:20 pm
ORD
- SJC
1 stop6h 51m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$330
This Expedia deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/68:00 am
SJC
- ORD
1 stop19h 00m
Multiple Airlines
Sun 8/169:13 pm
ORD
- SJC
1 stop24h 15m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/38:23 pm
SJC
- ORD
2 stops31h 14m
Frontier
Sat 8/89:13 pm
ORD
- SJC
1 stop24h 15m
Frontier
Deal found 6/3![Frontier logo]()
$332
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:12 pm
SJC
- ORD
2 stops12h 18m
Delta
Tue 7/146:30 am
ORD
- SJC
1 stop7h 31m
Delta
Deal found 6/1![Delta logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:12 pm
SJC
- ORD
1 stop12h 55m
Frontier
Tue 7/79:57 pm
ORD
- SJC
2 stops47h 31m
Frontier
Deal found 6/2![Frontier logo]()
$335
This Southwest deal was found by Cheapflights users on 6/2. 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.
Wed 8/2611:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Mon 8/316:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 6/2![Southwest 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 June 6, 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 6, 2026.
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Tue 9/223:30 pm
MDW
- SJC
1 stop7h 20m
Southwest
Deal found 6/2![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:00 am
SJC
- MDW
2 stops10h 18m
Delta
Thu 8/65:10 pm
MDW
- SJC
1 stop7h 48m
Delta
Deal found 6/2![Delta logo]()
$351
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Fri 8/212:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Tue 9/18:59 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 6/2![United Airlines logo]()
$430
This Alaska Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 6/189:09 am
SJC
- ORD
1 stop7h 48m
Alaska Airlines
Mon 6/296:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/5![Alaska Airlines logo]()
$483
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 10/162:24 pm
SJC
- RFD
2 stops27h 44m
Multiple Airlines
Sun 11/18:53 pm
RFD
- SJC
1 stop18h 36m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$499
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:30 pm
SJC
- MDW
1 stop7h 10m
Southwest
Thu 9/248:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 6/2![Southwest logo]()
$348
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 9/2912:46 pm
SJC
- MDW
1 stop7h 39m
Delta
Sun 10/41:47 pm
MDW
- SJC
1 stop8h 46m
Delta
Deal found 6/5![Delta logo]()
$355
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 9/279:20 pm
SJC
- MDW
1 stop6h 20m
Southwest
Tue 10/1310:30 am
MDW
- SJC
1 stop7h 50m
Southwest
Deal found 6/5![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:46 pm
SJC
- MDW
1 stop7h 39m
Delta
Mon 9/219:49 am
MDW
- SJC
2 stops9h 24m
Delta
Deal found 6/1![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
Sun 9/278:25 pm
SJC
- MDW
2 stops10h 25m
Delta
Tue 10/136:00 am
MDW
- SJC
1 stop7h 56m
Delta
Deal found 6/5![Delta logo]()
$360
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/56:30 am
SJC
- ORD
Nonstop4h 24m
United Airlines
Sat 8/87:58 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 6/4![United Airlines logo]()
$438
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:35 pm
SJC
- MDW
1 stop7h 05m
Southwest
Tue 7/75:25 am
MDW
- SJC
1 stop7h 35m
Southwest
Deal found 6/5![Southwest logo]()
$370
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/2112:37 pm
SJC
- MDW
1 stop7h 59m
Delta
Tue 9/16:05 am
MDW
- SJC
1 stop7h 22m
Delta
Deal found 6/5![Delta logo]()
$360
This Southwest deal was found by Cheapflights users on 6/2. 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 7/1410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sun 7/196:10 am
MDW
- SJC
1 stop6h 20m
Southwest
Deal found 6/2![Southwest logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 6/3. 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.
Wed 6/246:17 am
SJC
- ORD
2 stops20h 43m
Alaska Airlines
Thu 7/166:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$499
This United Airlines deal was found by Cheapflights users on 6/1. 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.
Thu 6/251:10 pm
SJC
- ORD
1 stop8h 05m
United Airlines
Mon 6/297:55 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 6/1![United Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 10/16:10 pm
SJC
- MDW
2 stops12h 57m
Delta
Fri 10/21:47 pm
MDW
- SJC
1 stop8h 46m
Delta
Deal found 6/5![Delta logo]()
$368
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/66:30 am
SJC
- ORD
Nonstop4h 24m
United Airlines
Sun 8/168:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 6/5![United Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:00 am
SJC
- ORD
2 stops9h 57m
Delta
Wed 7/82:02 pm
ORD
- SJC
2 stops10h 11m
Delta
Deal found 6/1![Delta logo]()
$437
This United Airlines deal was found by Cheapflights users on 6/2. 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 8/48:45 am
SJC
- ORD
1 stop6h 20m
United Airlines
Wed 8/128:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 6/2![United Airlines logo]()
$555
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:30 am
SJC
- ORD
Nonstop4h 24m
United Airlines
Thu 7/97:58 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 6/2![United Airlines logo]()
$562
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/97:00 am
SJC
- ORD
2 stops9h 57m
Delta
Sun 7/127:45 am
ORD
- SJC
1 stop7h 00m
Delta
Deal found 6/2![Delta logo]()
$541
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/276:12 pm
SJC
- ORD
2 stops11h 47m
Delta
Sun 8/27:45 am
ORD
- SJC
1 stop7h 00m
Delta
Deal found 6/5![Delta logo]()
$618
Last-minute flights from San Jose to ChicagoDiscover last-minute flight deals from San Jose to Chicago. Data last updated June 6, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Chicago. Data last updated June 6, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/1. 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 6/234:00 pm
SJC
- ORD
1 stop6h 44m
United Airlines
Tue 6/306:30 am
ORD
- SJC
1 stop7h 33m
United Airlines
Deal found 6/1![United Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:12 pm
SJC
- ORD
1 stop12h 55m
Frontier
Tue 7/79:57 pm
ORD
- SJC
2 stops47h 31m
Frontier
Deal found 6/2![Frontier logo]()
$335
This Alaska Airlines deal was found by Cheapflights users on 6/3. 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.
Tue 6/303:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Fri 7/102:20 pm
ORD
- SJC
1 stop6h 51m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$330
This Southwest deal was found by Cheapflights users on 6/1. 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 7/410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 7/76:10 am
MDW
- SJC
1 stop7h 15m
Southwest
Deal found 6/1![Southwest logo]()
$340
This Alaska Airlines deal was found by Cheapflights users on 6/3. 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.
Sat 7/49:09 am
SJC
- ORD
1 stop8h 28m
Alaska Airlines
Wed 7/156:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:12 pm
SJC
- ORD
2 stops12h 18m
Delta
Tue 7/146:30 am
ORD
- SJC
1 stop7h 31m
Delta
Deal found 6/1![Delta logo]()
$334
This Expedia deal was found by Cheapflights users on 6/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:37 pm
SJC
- ORD
1 stop8h 23m
Alaska Airlines
Tue 7/147:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 6/2. 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 7/1410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 7/218:55 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 6/2![Southwest logo]()
$330
This Expedia deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Sat 8/17:15 am
ORD
- SJC
1 stop8h 02m
Frontier
Deal found 6/2![Frontier logo]()
$338
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/204:20 pm
SJC
- MDW
1 stop6h 00m
Southwest
Wed 7/298:55 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 6/2![Southwest logo]()
$336
This SmartFares deal was found by Cheapflights users on 6/1. 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 SmartFares 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 8/46:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$314
This Alaska Airlines deal was found by Cheapflights users on 6/2. 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 7/307:13 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Thu 8/66:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 6/2![Alaska Airlines logo]()
$318
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 6, 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 6, 2026.
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:20 am
SJC
- MDW
2 stops10h 05m
Delta
Deal found 6/2![Delta logo]()
$142
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/189:34 am
SJC
- ORD
2 stops10h 24m
Delta
Deal found 6/2![Delta logo]()
$142
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Deal found 6/1![Delta logo]()
$145
This Delta deal was found by Cheapflights users on 6/2. 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.
Mon 8/176:59 am
SJC
- ORD
1 stop8h 41m
Delta
Deal found 6/2![Delta logo]()
$145
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/78:59 pm
SJC
- MDW
2 stops9h 38m
Delta
Deal found 6/5![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
SJC
- ORD
2 stops8h 23m
Delta
Deal found 6/4![Delta logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 6/1. 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.
Sun 8/168:23 pm
SJC
- ORD
1 stop31h 54m
Frontier
Deal found 6/1![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 6/2. 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 7/38:25 pm
SJC
- ORD
1 stop31h 54m
Frontier
Deal found 6/2![Frontier logo]()
$149
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:59 am
SJC
- ORD
2 stops12h 48m
Delta
Deal found 6/1![Delta logo]()
$150
This Trip.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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.
Sat 7/188:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 6/6![Frontier logo]()
$151
This Trip.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:25 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 6/3![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/118:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 6/4![Frontier logo]()
$154
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 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $313 (CheapOair) |
One-way from | $142 (Delta) |
Popular in | March |
Cheapest in | February |
Average price | $464 |
Good round-trip deal | $497 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 June 6, 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
Thu 9/17
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Tue 9/22
3:30 pm-8:50 pm
1 stop7h 20m
$336
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 9/17
8:30 pm-5:40 am
1 stop7h 10m
Chicago Midway
Thu 9/24
8:50 pm-11:20 pm
Nonstop4h 30m
$348
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 7/28
6:00 am-6:18 pm
2 stops10h 18m
Chicago Midway
Thu 8/6
5:10 pm-10:58 pm
1 stop7h 48m
$351
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 9/29
12:46 pm-10:25 pm
1 stop7h 39m
Chicago Midway
Sun 10/4
1:47 pm-8:33 pm
1 stop8h 46m
$355
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sun 9/27
9:20 pm-5:40 am
1 stop6h 20m
Chicago Midway
Tue 10/13
10:30 am-4:20 pm
1 stop7h 50m
$355
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 9/17
12:46 pm-10:25 pm
1 stop7h 39m
Chicago Midway
Mon 9/21
9:49 am-5:13 pm
2 stops9h 24m
$359
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sun 9/27
8:25 pm-8:50 am
2 stops10h 25m
Chicago Midway
Tue 10/13
6:00 am-11:56 am
1 stop7h 56m
$360
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 8/21
12:37 pm-10:36 pm
1 stop7h 59m
Chicago Midway
Tue 9/1
6:05 am-11:27 am
1 stop7h 22m
$360
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 10/1
6:10 pm-9:07 am
2 stops12h 57m
Chicago Midway
Fri 10/2
1:47 pm-8:33 pm
1 stop8h 46m
$368
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 6/30
7:35 pm-4:40 am
1 stop7h 05m
Chicago Midway
Tue 7/7
5:25 am-11:00 am
1 stop7h 35m
$370
Showing 1-10 of 53 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 | |
| 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 6, 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 6, 2026.
The most flights from SJC to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 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 3 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 6, 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.
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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
Lansing
Merrillville
Hammond
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 June 6, 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 June 6, 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 6, 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 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$131 | Average$390 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$424 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$235 | Average$339 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$236 | Average$371 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$517 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$280 | Average$559 | FlexibilityNo cancel fee | On-time69% |