$123+ Cheap flights from San Jose, CA (SJC) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Dec 9 — Dec 161
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 April, booked 70 days in advance, depart on a Wednesday or Tuesday 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 November 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 November 9, 2026.
This Frontier deal was found by Cheapflights users on 11/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:59 pm -
1 stop9h 50m
Wed 12/307:35 am -
1 stop11h 29m
Deal found 11/5![Frontier logo]()
$338
This Frontier deal was found by Cheapflights users on 11/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:10 pm -
1 stop13h 04m
Thu 11/265:15 am -
1 stop12h 15m
Deal found 11/5![Frontier logo]()
$340
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/99:54 am -
1 stop7h 06m
Sun 12/136:00 am -
1 stop30h 58m
Deal found 11/4![Alaska Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Tue 12/295:59 pm -
1 stop9h 50m
Mon 1/48:14 pm -
2 stops50h 50m
Deal found 11/8![Frontier logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/33:52 pm -
1 stop11h 07m
Sat 1/94:34 pm -
2 stops21h 38m
Deal found 11/6![Frontier logo]()
$344
This Frontier deal was found by Cheapflights users on 11/4. 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.
Thu 11/263:10 pm -
1 stop13h 04m
Mon 11/305:15 am -
1 stop12h 15m
Deal found 11/4![Frontier logo]()
$345
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/29:54 am -
1 stop7h 06m
Thu 1/72:13 pm -
1 stop8h 58m
Deal found 11/6![Alaska Airlines logo]()
$346
This Expedia deal was found by Cheapflights users on 11/4. 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.
Tue 12/1511:59 am -
1 stop10h 00m
Sat 12/195:40 am -
1 stop10h 50m
Deal found 11/4![Multiple Airlines logo]()
$347
This Travelocity deal was found by Cheapflights users on 11/4. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1011:38 am -
1 stop10h 21m
Sun 1/37:58 pm -
1 stop16h 52m
Deal found 11/4![Alaska Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 11/5. 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.
Thu 12/36:00 am -
Nonstop4h 10m
Thu 12/1010:10 am -
Nonstop4h 45m
Deal found 11/5![Southwest logo]()
$349
This United Airlines deal was found by Cheapflights users on 11/5. 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 11/266:30 am -
Nonstop4h 24m
Thu 12/39:07 am -
Nonstop4h 52m
Deal found 11/5![United Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/143:48 pm -
1 stop11h 13m
Sat 1/25:40 am -
1 stop10h 50m
Deal found 11/6![Frontier logo]()
$350
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 November 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 November 9, 2026.
This United Airlines deal was found by Cheapflights users on 11/5. 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 12/32:11 pm -
Nonstop4h 19m
Thu 12/109:07 am -
Nonstop4h 52m
Deal found 11/5![United Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 11/8. 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.
Wed 1/66:05 am -
Nonstop4h 05m
Mon 1/117:45 pm -
Nonstop4h 50m
Deal found 11/8![Southwest logo]()
$386
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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 3/295:15 pm -
1 stop17h 49m
Fri 4/22:30 pm -
1 stop6h 38m
Deal found 11/8![Alaska Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 11/8. 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 12/111:38 am -
2 stops8h 18m
Wed 12/212:34 pm -
2 stops11h 42m
Deal found 11/8![Delta logo]()
$401
This Southwest deal was found by Cheapflights users on 11/5. 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.
Mon 1/1810:55 pm -
Nonstop4h 10m
Thu 1/2111:55 am -
2 stops7h 45m
Deal found 11/5![Southwest logo]()
$388
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Wed 1/64:05 pm -
1 stop5h 53m
Mon 1/119:07 am -
Nonstop5h 02m
Deal found 11/8![United Airlines logo]()
$396
This Southwest deal was found by Cheapflights users on 11/4. 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 12/166:00 am -
Nonstop4h 10m
Sat 12/196:20 pm -
1 stop7h 35m
Deal found 11/4![Southwest logo]()
$398
This Delta deal was found by Cheapflights users on 11/5. 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 1/188:57 pm -
2 stops10h 01m
Thu 1/216:00 am -
2 stops10h 36m
Deal found 11/5![Delta logo]()
$460
This Southwest deal was found by Cheapflights users on 11/8. 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.
Mon 12/711:10 am -
Nonstop4h 05m
Fri 12/119:15 pm -
Nonstop4h 40m
Deal found 11/8![Southwest logo]()
$411
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/268:20 pm -
1 stop14h 59m
Fri 1/17:00 am -
1 stop8h 55m
Deal found 11/5![Alaska Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 11/7. 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 11/302:14 pm -
Nonstop4h 18m
Thu 12/38:40 am -
1 stop8h 28m
Deal found 11/7![United Airlines logo]()
$474
This Delta deal was found by Cheapflights users on 11/5. 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 3/298:05 pm -
2 stops10h 29m
Fri 4/26:00 am -
2 stops8h 28m
Deal found 11/5![Delta logo]()
$517
This Southwest deal was found by Cheapflights users on 11/6. 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.
Thu 12/318:10 am -
2 stops7h 10m
Mon 1/47:30 am -
1 stop8h 25m
Deal found 11/6![Southwest logo]()
$432
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Mon 11/302:14 pm -
Nonstop4h 18m
Fri 12/48:40 am -
1 stop8h 27m
Deal found 11/8![United Airlines logo]()
$484
This Southwest deal was found by Cheapflights users on 11/5. 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 12/239:40 pm -
1 stop6h 05m
Thu 12/313:55 pm -
1 stop7h 50m
Deal found 11/5![Southwest logo]()
$447
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Sat 12/124:00 pm -
1 stop5h 59m
Wed 12/169:07 am -
Nonstop4h 52m
Deal found 11/6![United Airlines logo]()
$501
This Southwest deal was found by Cheapflights users on 11/4. 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.
Mon 12/2111:00 pm -
Nonstop4h 00m
Thu 12/313:50 pm -
Nonstop4h 40m
Deal found 11/4![Southwest logo]()
$457
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/2311:00 pm -
Nonstop4h 17m
Fri 12/252:47 pm -
1 stop8h 11m
Deal found 11/6![United Airlines logo]()
$535
This Southwest deal was found by Cheapflights users on 11/6. 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.
Wed 12/234:40 pm -
1 stop6h 00m
Fri 12/2510:10 am -
Nonstop4h 45m
Deal found 11/6![Southwest logo]()
$474
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Thu 12/3111:00 pm -
Nonstop4h 17m
Mon 1/47:45 pm -
Nonstop5h 00m
Deal found 11/4![United Airlines logo]()
$538
This Southwest deal was found by Cheapflights users on 11/8. 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.
Mon 11/3011:00 pm -
Nonstop4h 00m
Fri 12/410:10 am -
Nonstop4h 45m
Deal found 11/8![Southwest logo]()
$504
This Southwest deal was found by Cheapflights users on 11/8. 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.
Mon 11/3011:00 pm -
Nonstop4h 00m
Thu 12/33:50 pm -
Nonstop4h 40m
Deal found 11/8![Southwest logo]()
$504
Last-minute flights from San Jose to ChicagoDiscover last-minute flight deals from San Jose to Chicago. Data last updated November 9, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Chicago. Data last updated November 9, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 11/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:10 pm -
1 stop13h 04m
Wed 11/255:15 am -
1 stop12h 15m
Deal found 11/5![Frontier logo]()
$340
This Frontier deal was found by Cheapflights users on 11/4. 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.
Thu 11/263:10 pm -
1 stop13h 04m
Mon 11/305:15 am -
1 stop12h 15m
Deal found 11/4![Frontier logo]()
$345
This United Airlines deal was found by Cheapflights users on 11/5. 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 11/266:30 am -
Nonstop4h 24m
Thu 12/39:07 am -
Nonstop4h 52m
Deal found 11/5![United Airlines logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/29:54 am -
1 stop7h 06m
Thu 1/72:13 pm -
1 stop8h 58m
Deal found 11/6![Alaska Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/33:52 pm -
1 stop11h 07m
Sat 1/94:34 pm -
2 stops21h 38m
Deal found 11/6![Frontier logo]()
$344
This Southwest deal was found by Cheapflights users on 11/5. 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.
Thu 12/36:00 am -
Nonstop4h 10m
Thu 12/1010:10 am -
Nonstop4h 45m
Deal found 11/5![Southwest logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/99:54 am -
1 stop7h 06m
Sun 12/136:00 am -
1 stop30h 58m
Deal found 11/4![Alaska Airlines logo]()
$341
This Priceline deal was found by Cheapflights users on 11/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1011:59 am -
1 stop10h 00m
Sun 12/132:13 pm -
1 stop8h 43m
Deal found 11/5![Alaska Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/143:48 pm -
1 stop11h 13m
Sat 1/25:40 am -
1 stop10h 50m
Deal found 11/6![Frontier logo]()
$350
This Expedia deal was found by Cheapflights users on 11/4. 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.
Tue 12/1511:59 am -
1 stop10h 00m
Sat 12/195:40 am -
1 stop10h 50m
Deal found 11/4![Multiple Airlines logo]()
$347
This Frontier deal was found by Cheapflights users on 11/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:59 pm -
1 stop9h 50m
Wed 12/307:35 am -
1 stop11h 29m
Deal found 11/5![Frontier logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Tue 12/295:59 pm -
1 stop9h 50m
Mon 1/48:14 pm -
2 stops50h 50m
Deal found 11/8![Frontier logo]()
$343
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 November 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 November 9, 2026.
This Super.com deal was found by Cheapflights users on 11/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/99:59 pm -
1 stop6h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Tue 2/912:58 pm -
2 stops21h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$126
This Super.com deal was found by Cheapflights users on 11/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/2712:58 pm -
1 stop15h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sun 1/109:59 pm -
2 stops24h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 11/4. 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 12/143:48 pm -
1 stop11h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Tue 2/912:58 pm -
2 stops20h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Tue 2/212:58 pm -
2 stops25h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$133
This Orbitz deal was found by Cheapflights users on 11/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/3112:58 pm -
1 stop15h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Frontier logo]()
$134
This Priceline deal was found by Cheapflights users on 11/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:52 pm -
1 stop11h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/42:47 pm -
2 stops12h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 1/145:25 pm -
2 stops29h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Frontier logo]()
$148
This Mytrip deal was found by Cheapflights users on 11/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:47 pm -
2 stops18h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$159
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 November 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $337 (Kiwi.com) |
One-way from | $123 (Super.com) |
Popular in | March |
Cheapest in | February |
Average price | $413 |
Good round-trip deal | $399 or less |
Good one-way deal | $210 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 7,457,451 searches. Data last updated November 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 San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Thu 12/10
11:59 am-11:59 pm
1 stop10h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$155
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Fri 12/11
3:23 pm-11:59 pm
1 stop6h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$155
Quickest round-trip
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Thu 12/3
6:00 am-12:10 pm
Nonstop4h 10m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$175
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Wed 1/20
10:20 am-10:28 pm
1 stop10h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$182
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 1/13
6:30 am-4:55 pm
1 stop8h 25m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$185
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 1/20
6:30 am-4:54 pm
1 stop8h 24m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$185
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Mon 12/14
10:30 pm-10:28 am
1 stop9h 58m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$185
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Thu 1/21
2:25 pm-11:55 pm
1 stop7h 30m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$185
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Sat 1/16
7:00 am-10:08 pm
2 stops13h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$188
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Thu 11/26
11:38 am-10:54 pm
2 stops9h 16m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$190
Showing 1-10 of 41 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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
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
What is the cheapest month to book a flight from San Jose, California to Chicago?
Currently, April is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $405). Flying from San Jose, California to Chicago in June is currently the most expensive (average of $573). 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 November 9, 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 23% on your trip compared to booking a flight at noon.
How much does it cost to fly round-trip from San Jose, California to Chicago?
Airfare is below average for this route at the moment.
San Jose, California to Chicago flights typically cost between $377 and $526 in January.The cheapest round-trip price found within the last 5 days was $337 on Frontier (Jan 6-Jan 11).
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.
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 November 9, 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.
Crew
8.6
Entertainment
7.4
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.4
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.4
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.4
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.4
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San Jose to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
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 November 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 November 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 November 9, 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 7,457,451 searches. Data last updated November 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$183 | Average$490 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$236 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$509 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$263 | Average$356 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$278 | Average$561 | FlexibilityNo cancel fee | On-time69% |