$129+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Jun 8 — Jun 151
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 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 May 9, 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 May 9, 2026.
This Expedia deal was found by Cheapflights users on 5/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:03 am
SJC
- ORD
1 stop6h 54m
Multiple Airlines
Mon 8/177:15 am
ORD
- SJC
1 stop8h 02m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 5/5. 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.
Wed 6/102:10 pm
SJC
- MDW
1 stop7h 40m
Southwest
Tue 6/166:00 am
MDW
- SJC
1 stop7h 25m
Southwest
Deal found 5/5![Southwest logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:14 pm
SJC
- ORD
1 stop7h 45m
Alaska Airlines
Wed 6/32:10 pm
ORD
- SJC
1 stop7h 12m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$277
This CheapOair deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:57 pm
SJC
- ORD
1 stop15h 37m
Frontier
Wed 5/278:46 pm
ORD
- SJC
1 stop17h 13m
Frontier
Deal found 5/8![Frontier logo]()
$280
This Mytrip deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:57 pm
SJC
- ORD
1 stop15h 22m
Frontier
Sun 8/309:07 pm
ORD
- SJC
1 stop16h 55m
Frontier
Deal found 5/7![Frontier logo]()
$281
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/21:45 pm
SJC
- MDW
1 stop6h 15m
Southwest
Wed 6/35:30 pm
MDW
- SJC
2 stops7h 30m
Southwest
Deal found 5/8![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/212:45 pm
SJC
- ORD
2 stops8h 10m
Southwest
Wed 6/34:50 pm
ORD
- SJC
1 stop7h 25m
Southwest
Deal found 5/8![Southwest logo]()
$282
This Expedia deal was found by Cheapflights users on 5/5. 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.
Tue 7/143:15 pm
SJC
- ORD
1 stop6h 21m
Multiple Airlines
Sat 7/189:13 pm
ORD
- SJC
1 stop24h 26m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$284
This Expedia deal was found by Cheapflights users on 5/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:06 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Wed 6/107:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$285
This Southwest deal was found by Cheapflights users on 5/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:45 am
SJC
- MDW
2 stops7h 45m
Southwest
Tue 6/95:25 am
MDW
- SJC
2 stops8h 00m
Southwest
Deal found 5/6![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/211:45 am
SJC
- ORD
1 stop10h 10m
Delta
Wed 6/37:45 am
ORD
- SJC
1 stop7h 03m
Delta
Deal found 5/8![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 5/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:00 am
SJC
- ORD
2 stops12h 57m
Delta
Tue 6/232:09 pm
ORD
- SJC
2 stops10h 07m
Delta
Deal found 5/6![Delta logo]()
$288
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 May 9, 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 May 9, 2026.
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/212:45 pm
SJC
- ORD
2 stops8h 10m
Southwest
Wed 6/34:50 pm
ORD
- SJC
1 stop8h 10m
Southwest
Deal found 5/7![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 5/4. 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.
Mon 9/285:45 pm
SJC
- MDW
2 stops12h 53m
Delta
Wed 9/306:00 am
MDW
- SJC
2 stops12h 15m
Delta
Deal found 5/4![Delta logo]()
$352
This Alaska Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/282:25 pm
SJC
- ORD
1 stop7h 32m
Alaska Airlines
Thu 10/19:00 am
ORD
- SJC
1 stop8h 51m
Alaska Airlines
Deal found 5/8![Alaska Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 7/141:10 pm
SJC
- ORD
1 stop9h 35m
United Airlines
Mon 7/207:55 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 5/8![United Airlines logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Thu 6/412:57 pm
SJC
- RFD
2 stops29h 23m
Multiple Airlines
Sun 6/141:13 pm
RFD
- SJC
1 stop26h 04m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 5/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/411:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Tue 9/88:35 am
MDW
- SJC
2 stops7h 55m
Southwest
Deal found 5/4![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:00 am
SJC
- ORD
2 stops10h 30m
Delta
Mon 7/208:52 am
ORD
- SJC
2 stops10h 20m
Delta
Deal found 5/8![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 5/4. 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.
Wed 6/36:00 am
SJC
- ORD
2 stops10h 05m
Delta
Sun 6/76:30 am
ORD
- SJC
2 stops11h 23m
Delta
Deal found 5/4![Delta logo]()
$372
This United Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 9/296:40 am
SJC
- ORD
Nonstop4h 20m
United Airlines
Thu 10/18:00 pm
ORD
- SJC
Nonstop4h 36m
United Airlines
Deal found 5/4![United Airlines logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 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
Sun 9/139:29 pm
RFD
- SJC
2 stops24h 39m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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
Mon 9/2110:15 am
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/8![Southwest logo]()
$407
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 5/198:15 pm
SJC
- ORD
1 stop8h 05m
Alaska Airlines
Wed 5/209:00 am
ORD
- SJC
1 stop7h 13m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$451
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:55 pm
SJC
- ORD
2 stops12h 35m
Delta
Sun 7/196:30 am
ORD
- SJC
2 stops11h 16m
Delta
Deal found 5/8![Delta logo]()
$383
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:09 pm
SJC
- ORD
Nonstop4h 23m
United Airlines
Tue 9/18:40 am
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 5/6![United Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 7/2410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sun 7/269:25 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/8![Southwest logo]()
$407
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/2212:46 pm
SJC
- MDW
1 stop7h 31m
Delta
Wed 7/16:00 am
MDW
- SJC
1 stop7h 36m
Delta
Deal found 5/7![Delta logo]()
$385
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/2010:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sat 7/258:25 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/7![Southwest logo]()
$407
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/202:32 pm
SJC
- ORD
1 stop8h 12m
United Airlines
Sat 7/257:55 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 5/7![United Airlines logo]()
$455
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/192:12 pm
SJC
- RFD
2 stops20h 02m
Multiple Airlines
Sun 6/211:13 pm
RFD
- SJC
1 stop26h 04m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$537
This Southwest deal was found by Cheapflights users on 5/5. 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.
Sat 9/511:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Tue 9/83:30 pm
MDW
- SJC
1 stop7h 20m
Southwest
Deal found 5/5![Southwest logo]()
$411
This Delta deal was found by Cheapflights users on 5/4. 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.
Fri 9/259:05 am
SJC
- ORD
2 stops10h 29m
Delta
Sat 9/263:50 pm
ORD
- SJC
1 stop7h 03m
Delta
Deal found 5/4![Delta logo]()
$432
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:40 am
SJC
- ORD
Nonstop4h 20m
United Airlines
Thu 10/18:00 pm
ORD
- SJC
Nonstop4h 36m
United Airlines
Deal found 5/6![United Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/202:12 pm
SJC
- RFD
1 stop20h 11m
Multiple Airlines
Wed 6/248:50 pm
RFD
- SJC
2 stops18h 27m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$557
This Southwest deal was found by Cheapflights users on 5/5. 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.
Sat 6/62:05 pm
SJC
- MDW
1 stop5h 50m
Southwest
Sun 6/75:25 am
MDW
- SJC
1 stop7h 10m
Southwest
Deal found 5/5![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/115:00 pm
SJC
- MDW
1 stop6h 25m
Southwest
Tue 6/168:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/8![Southwest logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 5/232:12 pm
SJC
- RFD
1 stop20h 09m
Multiple Airlines
Wed 5/278:55 pm
RFD
- SJC
2 stops41h 04m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$657
Last-minute flights from San Jose to ChicagoDiscover last-minute flight deals from San Jose to Chicago. Data last updated May 9, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Chicago. Data last updated May 9, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:57 pm
SJC
- ORD
1 stop15h 37m
Frontier
Wed 5/278:46 pm
ORD
- SJC
1 stop17h 13m
Frontier
Deal found 5/8![Frontier logo]()
$280
This CheapOair deal was found by Cheapflights users on 5/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2412:57 pm
SJC
- ORD
1 stop15h 37m
Frontier
Sat 5/308:46 pm
ORD
- SJC
1 stop17h 13m
Frontier
Deal found 5/6![Frontier logo]()
$290
This Booking.com deal was found by Cheapflights users on 5/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2512:57 pm
SJC
- ORD
1 stop15h 37m
Frontier
Thu 5/288:46 pm
ORD
- SJC
1 stop17h 13m
Frontier
Deal found 5/5![Frontier logo]()
$294
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:14 pm
SJC
- ORD
1 stop7h 45m
Alaska Airlines
Wed 6/32:10 pm
ORD
- SJC
1 stop7h 12m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/21:45 pm
SJC
- MDW
1 stop6h 15m
Southwest
Wed 6/35:30 pm
MDW
- SJC
2 stops7h 30m
Southwest
Deal found 5/8![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/212:45 pm
SJC
- ORD
2 stops8h 10m
Southwest
Wed 6/34:50 pm
ORD
- SJC
1 stop7h 25m
Southwest
Deal found 5/8![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:05 pm
SJC
- MDW
2 stops10h 37m
Delta
Wed 6/31:22 pm
MDW
- SJC
2 stops10h 52m
Delta
Deal found 5/8![Delta logo]()
$298
This Expedia deal was found by Cheapflights users on 5/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:06 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Wed 6/107:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$285
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Sat 6/67:06 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Tue 6/97:40 am
ORD
- SJC
1 stop8h 00m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 5/5. 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.
Wed 6/102:10 pm
SJC
- MDW
1 stop7h 40m
Southwest
Tue 6/235:30 am
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 5/5![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 5/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/102:10 pm
SJC
- MDW
1 stop7h 40m
Southwest
Tue 6/168:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/4![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 5/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:00 am
SJC
- ORD
2 stops12h 57m
Delta
Tue 6/232:09 pm
ORD
- SJC
2 stops10h 07m
Delta
Deal found 5/6![Delta logo]()
$288
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 May 9, 2026.
Search for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Data last updated May 9, 2026.
This Delta deal was found by Cheapflights users on 5/4. 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 5/2610:00 pm
SJC
- MDW
1 stop10h 00m
Delta
Deal found 5/4![Delta logo]()
$129
This Delta deal was found by Cheapflights users on 5/4. 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 5/2612:12 pm
SJC
- ORD
1 stop8h 15m
Delta
Deal found 5/4![Delta logo]()
$129
This Frontier deal was found by Cheapflights users on 5/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/152:12 pm
SJC
- ORD
1 stop12h 55m
Frontier
Deal found 5/4![Frontier logo]()
$131
This Delta deal was found by Cheapflights users on 5/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:00 pm
SJC
- MDW
1 stop10h 00m
Delta
Deal found 5/6![Delta logo]()
$144
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/212:45 pm
SJC
- ORD
2 stops9h 10m
Southwest
Deal found 5/8![Southwest logo]()
$144
This Frontier deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/178:25 pm
SJC
- ORD
1 stop7h 52m
Frontier
Deal found 5/7![Frontier logo]()
$145
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:45 pm
SJC
- ORD
2 stops12h 51m
Delta
Deal found 5/7![Delta logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Mon 6/112:57 pm
SJC
- ORD
2 stops29h 35m
Frontier
Deal found 5/5![Frontier logo]()
$150
This Frontier deal was found by Cheapflights users on 5/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/222:12 pm
SJC
- ORD
1 stop12h 55m
Frontier
Deal found 5/6![Frontier logo]()
$151
This Booking.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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.
Sun 5/3112:57 pm
SJC
- ORD
1 stop15h 37m
Frontier
Deal found 5/8![Frontier logo]()
$152
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/163:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$154
This Mytrip deal was found by Cheapflights users on 5/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:57 pm
SJC
- ORD
1 stop15h 22m
Frontier
Deal found 5/6![Frontier logo]()
$155
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 May 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $273 (Expedia) |
One-way from | $129 (Delta) |
Popular in | March |
Cheapest in | February |
Average price | $462 |
Good round-trip deal | $434 or less |
Good one-way deal | $203 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 May 9, 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
Tue 6/2
12:45 pm-10:55 pm
2 stops8h 10m
Chicago O'Hare Intl
Wed 6/3
4:50 pm-11:00 pm
1 stop8h 10m
$282
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 9/4
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Tue 9/8
8:35 am-2:30 pm
2 stops7h 55m
$337
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 9/28
5:45 pm-8:38 am
2 stops12h 53m
Chicago Midway
Wed 9/30
6:00 am-4:15 pm
2 stops12h 15m
$352
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 9/28
2:25 pm-11:57 pm
1 stop7h 32m
Chicago O'Hare Intl
Thu 10/1
9:00 am-3:51 pm
1 stop8h 51m
$357
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 7/15
7:00 am-7:30 pm
2 stops10h 30m
Chicago O'Hare Intl
Mon 7/20
8:52 am-5:12 pm
2 stops10h 20m
$362
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 6/3
6:00 am-6:05 pm
2 stops10h 05m
Chicago O'Hare Intl
Sun 6/7
6:30 am-3:53 pm
2 stops11h 23m
$372
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 7/15
5:55 pm-8:30 am
2 stops12h 35m
Chicago O'Hare Intl
Sun 7/19
6:30 am-3:46 pm
2 stops11h 16m
$383
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 6/22
12:46 pm-10:17 pm
1 stop7h 31m
Chicago Midway
Wed 7/1
6:00 am-11:36 am
1 stop7h 36m
$385
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 7/14
1:10 pm-12:45 am
1 stop9h 35m
Chicago O'Hare Intl
Mon 7/20
7:55 pm-10:40 pm
Nonstop4h 45m
$396
Quickest round-trip
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 9/17
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Mon 9/21
10:15 am-12:45 pm
Nonstop4h 30m
$407
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 May.
| 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-MDW
SJC-ORD
SJC-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Jose to Chicago
SJC-CHI
SJC-MDW
SJC-ORD
SJC-RFD
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 88 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.
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 December is currently the most expensive (average of $258). 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 May 9, 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 12% 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 May 9, 2026.
The most flights from SJC to CHI are scheduled on a Monday (3 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?
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 May 9, 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.
Boarding
8.1
Overall
7.9
Entertainment
7.0
Crew
8.5
Comfort
7.8
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Entertainment
7.0
Crew
8.5
Comfort
7.8
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Entertainment
7.0
Crew
8.5
Comfort
7.8
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Entertainment
7.0
Crew
8.5
Comfort
7.8
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Entertainment
7.0
Crew
8.5
Comfort
7.8
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Entertainment
7.0
Crew
8.5
Comfort
7.8
Food
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
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 May 9, 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 May 9, 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 May 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from San Jose to Chicago
Discover the top 7 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 May 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$239 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$337 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$324 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$200 | Average$424 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$208 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$517 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$272 | Average$536 | FlexibilityNo cancel fee | On-time69% |