$169+ Cheap flights from San Jose, CA (SJC) to O'Hare Intl (ORD)
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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Oct 15 — Oct 221
Round-trip
1 adult, Economy
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Find cheap flights from San Jose to O'Hare Intl 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 O'Hare Intl are usually found in May or September, booked 56 days in advance, depart on a Wednesday or Saturday and return on a Saturday
Cheap flight deals from San Jose to O'Hare Intl
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Best
Last-minute
One-way
Cheapest flights from San Jose to O'Hare IntlExplore the most affordable flight options available from San Jose to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
Explore the most affordable flight options available from San Jose to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/17:29 am -
1 stop9h 52m
Tue 10/69:00 am -
1 stop8h 52m
Deal found 9/9![Alaska Airlines logo]()
$295
This Orbitz deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
Fri 10/162:15 pm -
1 stop14h 19m
Sun 10/183:30 pm -
1 stop23h 50m
Deal found 9/12![Frontier logo]()
$297
This Expedia deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/292:41 pm -
1 stop12h 32m
Sun 11/15:15 pm -
1 stop22h 31m
Deal found 9/10![Frontier logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:38 pm -
1 stop14h 00m
Sun 10/48:55 pm -
2 stops24h 58m
Deal found 9/9![Frontier logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/169:02 pm -
2 stops31h 32m
Wed 10/218:01 pm -
1 stop26h 06m
Deal found 9/11![Frontier logo]()
$302
This Orbitz deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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.
Thu 10/222:15 pm -
1 stop14h 19m
Sun 10/253:30 pm -
1 stop23h 50m
Deal found 9/11![Frontier logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/92:15 pm -
1 stop14h 19m
Sat 10/108:01 pm -
1 stop26h 06m
Deal found 9/10![Frontier logo]()
$304
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:11 pm -
1 stop6h 24m
Tue 10/135:00 am -
1 stop9h 09m
Deal found 9/14![American Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:38 pm -
1 stop14h 00m
Thu 10/224:41 pm -
2 stops22h 39m
Deal found 9/9![Frontier logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/192:15 pm -
1 stop14h 19m
Fri 10/238:01 pm -
2 stops43h 19m
Deal found 9/10![Frontier logo]()
$311
This Travelocity deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
Fri 10/232:15 pm -
1 stop14h 19m
Tue 10/277:00 am -
1 stop8h 18m
Deal found 9/13![Multiple Airlines logo]()
$312
This Orbitz deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Mon 11/162:41 pm -
1 stop12h 32m
Wed 11/189:30 am -
2 stops11h 25m
Deal found 9/9![Multiple Airlines logo]()
$313
Best flights from San Jose to O'Hare IntlDiscover carefully curated flight deals from San Jose to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
Discover carefully curated flight deals from San Jose to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2511:12 am -
1 stop10h 47m
Thu 10/292:21 pm -
1 stop7h 08m
Deal found 9/13![Alaska Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/111:41 am -
2 stops10h 16m
Mon 10/52:05 pm -
2 stops10h 01m
Deal found 9/9![Delta logo]()
$411
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/22:08 pm -
Nonstop4h 27m
Sat 10/109:14 am -
Nonstop4h 47m
Deal found 9/10![United Airlines logo]()
$462
This Alaska Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/53:11 pm -
1 stop6h 38m
Sun 11/82:15 pm -
1 stop10h 16m
Deal found 9/9![Alaska Airlines logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/77:37 am -
1 stop9h 22m
Sun 11/157:57 pm -
1 stop15h 24m
Deal found 9/10![Alaska Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/611:41 am -
2 stops10h 16m
Wed 11/111:30 pm -
2 stops10h 42m
Deal found 9/11![Delta logo]()
$464
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/218:45 am -
1 stop8h 47m
Mon 11/239:02 am -
Nonstop5h 00m
Deal found 9/9![United Airlines logo]()
$474
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/257:33 pm -
2 stops10h 08m
Thu 10/2911:19 am -
2 stops12h 36m
Deal found 9/13![Delta logo]()
$487
This Alaska Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:33 am -
2 stops15h 26m
Wed 10/217:00 am -
2 stops12h 41m
Deal found 9/11![Alaska Airlines logo]()
$445
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/197:00 am -
2 stops12h 47m
Sun 11/227:35 am -
2 stops8h 41m
Deal found 9/10![Delta logo]()
$487
This Alaska Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 11/99:39 am -
1 stop7h 20m
Sat 11/142:07 pm -
1 stop7h 39m
Deal found 9/12![Alaska Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 9/262:13 pm -
1 stop7h 46m
Wed 9/302:22 pm -
1 stop7h 18m
Deal found 9/11![Alaska Airlines logo]()
$467
Last-minute flights from San Jose to O'Hare IntlDiscover last-minute flight deals from San Jose to O'Hare Intl. Data last updated September 15, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to O'Hare Intl. Data last updated September 15, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/17:29 am -
1 stop9h 52m
Tue 10/69:00 am -
1 stop8h 52m
Deal found 9/9![Alaska Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:38 pm -
1 stop14h 00m
Sun 10/48:55 pm -
2 stops24h 58m
Deal found 9/9![Frontier logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:38 pm -
1 stop14h 00m
Thu 10/224:41 pm -
2 stops22h 39m
Deal found 9/9![Frontier logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/92:15 pm -
1 stop14h 19m
Sat 10/108:01 pm -
1 stop26h 06m
Deal found 9/10![Frontier logo]()
$304
This Priceline deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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.
Fri 10/99:02 pm -
1 stop6h 14m
Fri 10/167:20 am -
1 stop9h 35m
Deal found 9/11![Multiple Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:11 pm -
1 stop6h 24m
Tue 10/135:00 am -
1 stop9h 09m
Deal found 9/14![American Airlines logo]()
$305
This Orbitz deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
Fri 10/162:15 pm -
1 stop14h 19m
Sun 10/183:30 pm -
1 stop23h 50m
Deal found 9/12![Frontier logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/169:02 pm -
2 stops31h 32m
Wed 10/218:01 pm -
1 stop26h 06m
Deal found 9/11![Frontier logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/192:15 pm -
1 stop14h 19m
Fri 10/238:01 pm -
2 stops43h 19m
Deal found 9/10![Frontier logo]()
$311
This Orbitz deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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.
Thu 10/222:15 pm -
1 stop14h 19m
Sun 10/253:30 pm -
1 stop23h 50m
Deal found 9/11![Frontier logo]()
$303
This Travelocity deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
Fri 10/232:15 pm -
1 stop14h 19m
Tue 10/277:00 am -
1 stop8h 18m
Deal found 9/13![Multiple Airlines logo]()
$312
This Expedia deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/292:41 pm -
1 stop12h 32m
Sun 11/15:15 pm -
1 stop22h 31m
Deal found 9/10![Frontier logo]()
$299
One-way flights from San Jose to O'Hare IntlSearch for one-way flight options from San Jose to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
Search for one-way flight options from San Jose to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
This Frontier deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/169:02 pm -
1 stop6h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$169
This CheapOair deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/82:41 pm -
1 stop12h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/69:07 pm -
2 stops25h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:15 pm -
2 stops32h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$173
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/57:30 am -
1 stop27h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Alaska Airlines logo]()
$174
This Frontier deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/292:41 pm -
1 stop12h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 12/101:48 pm -
2 stops19h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$177
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/36:10 am -
1 stop8h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$178
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/89:02 pm -
1 stop6h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/29:03 pm -
2 stops25h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$180
This Expedia deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/78:13 pm -
1 stop15h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Alaska Airlines logo]()
$184
Find flight deals from San Jose to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to O'Hare Intl (ORD). 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 September 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $295 (Alaska Airlines) |
One-way from | $169 (Frontier) |
Popular in | June |
Cheapest in | May |
Average price | $387 |
Good round-trip deal | $397 or less |
Good one-way deal | $243 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose to O'Hare Intl 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 September 15, 2026.
Use the filters below to find and compare flights from San Jose to Chicago O'Hare Intl Airport 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
Tue 10/6
9:15 am-6:53 pm
1 stop7h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$187
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Tue 12/1
9:54 am-7:00 pm
1 stop7h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Fri 10/2
12:51 pm-11:59 pm
1 stop9h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$205
Quickest round-trip
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Sun 11/15
2:14 pm-8:32 pm
Nonstop4h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$219
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Tue 10/6
6:00 am-4:40 pm
2 stops8h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$232
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Sun 10/4
6:30 am-12:52 pm
Nonstop4h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$239
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Sun 11/8
8:32 pm-8:41 am
2 stops10h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$244
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Thu 10/29
7:00 am-8:30 pm
2 stops11h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$244
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Sat 10/10
6:30 am-12:52 pm
Nonstop4h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$249
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Fri 12/11
2:15 pm-8:34 pm
Nonstop4h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$250
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from San Jose to O'Hare Intl
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 O'Hare Intl in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Jose, California-Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose, California-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Jose, California-Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from San Jose with our price prediction graph.
SJC-ORD
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 O'Hare Intl Airport
Prices
Airlines
How far ahead should I book a flight from San Jose, California to Chicago O'Hare Intl Airport?
Booking 55 days in advance of your planned departure date is, on average, the best time to get cheap flights from San Jose, California to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from San Jose, California to Chicago O'Hare Intl Airport?
Currently, May is the cheapest month in which you can book a flight from San Jose, California to Chicago O'Hare Intl Airport (average of $379). Flying from San Jose, California to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $577). 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 ORD?
Find hourly flight availability from San Jose to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from San Jose, California to Chicago O'Hare Intl Airport as you normally would.
The best insider tips for San Jose to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport trip
Our travel experts
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated September 15, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andDelta from San Jose to Chicago O'Hare Intl Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
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 O'Hare Intl. 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 O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsBenton Harbor
Rosemont
Des Plaines
Lake Geneva
Naperville
Glenview
Schaumburg
Oakbrook Terrace
Delavan
Oak Brook
Libertyville
Rockford
Hoffman Estates
Aurora
Beloit
Orland Park
South Holland
Elgin
Racine
Janesville
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Other flights to O'Hare Intl
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 15, 2026.
San Jose and O'Hare Intl flights
Browse other San Jose and O'Hare Intl flight options. Last updated on September 15, 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 September 15, 2026.
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Top 5 airlines flying from San Jose to O'Hare Intl
Discover the top 5 airlines that operate flights from San Jose to O'Hare Intl. 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 September 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$131 | Average$490 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$236 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$346 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$256 | Average$480 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$278 | Average$550 | FlexibilityNo cancel fee | On-time69% |