$144+ Cheap flights from San Jose, CA (SJC) to O'Hare Intl (ORD)
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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Jun 9 — Jun 161
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
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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 September or May, booked 4 days in advance, depart on a Wednesday or Saturday and return on a Wednesday
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 May 10, 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 May 10, 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 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 6/212:45 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 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
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 7/155:02 pm
SJC
- ORD
1 stop18h 19m
Multiple Airlines
Mon 7/207:15 am
ORD
- SJC
1 stop8h 02m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$289
This Frontier deal was found by Cheapflights users on 5/9. 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 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
Mon 6/297:20 am
ORD
- SJC
1 stop7h 57m
Frontier
Deal found 5/9![Frontier logo]()
$290
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
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 May 10, 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 May 10, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/161:40 pm
SJC
- ORD
1 stop6h 17m
Delta
Tue 6/237:45 am
ORD
- SJC
1 stop6h 53m
Delta
Deal found 5/5![Delta 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 United Airlines deal was found by Cheapflights users on 5/10. 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.
Sun 11/16:40 am
SJC
- ORD
Nonstop4h 20m
United Airlines
Sun 11/85:00 am
ORD
- SJC
1 stop6h 51m
United Airlines
Deal found 5/10![United Airlines logo]()
$417
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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.
Mon 6/87:06 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Sat 6/135:59 pm
ORD
- SJC
1 stop7h 55m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$347
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/301:40 pm
SJC
- ORD
1 stop6h 17m
Delta
Fri 7/105:30 am
ORD
- SJC
1 stop8h 00m
Delta
Deal found 5/5![Delta logo]()
$352
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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.
Tue 7/146:37 pm
SJC
- ORD
1 stop8h 23m
Alaska Airlines
Thu 7/306:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$347
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:00 am
SJC
- ORD
2 stops9h 58m
Delta
Fri 6/127:45 am
ORD
- SJC
2 stops11h 32m
Delta
Deal found 5/5![Delta logo]()
$362
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 9/301:05 pm
SJC
- ORD
1 stop7h 31m
United Airlines
Thu 10/18:00 pm
ORD
- SJC
Nonstop4h 36m
United Airlines
Deal found 5/6![United Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 5/9. 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.
Tue 6/306:00 am
SJC
- ORD
2 stops8h 26m
Delta
Mon 7/67:45 am
ORD
- SJC
1 stop6h 53m
Delta
Deal found 5/9![Delta logo]()
$440
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 8/266:30 am
SJC
- ORD
Nonstop4h 23m
United Airlines
Mon 8/317:55 pm
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 5/6![United Airlines logo]()
$505
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 7/71:10 pm
SJC
- ORD
1 stop9h 35m
United Airlines
Wed 7/157:55 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 5/8![United Airlines logo]()
$527
This Delta deal was found by Cheapflights users on 5/9. 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.
Mon 6/89:54 am
SJC
- ORD
1 stop11h 24m
Delta
Sun 6/146:30 am
ORD
- SJC
1 stop7h 35m
Delta
Deal found 5/9![Delta logo]()
$507
Last-minute flights from San Jose to O'Hare IntlDiscover last-minute flight deals from San Jose to O'Hare Intl. Data last updated May 10, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to O'Hare Intl. Data last updated May 10, 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 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 6/212:45 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 5/7. 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 6/210:00 pm
SJC
- ORD
1 stop10h 16m
Delta
Wed 6/107:45 am
ORD
- SJC
1 stop6h 53m
Delta
Deal found 5/7![Delta logo]()
$287
This Alaska 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 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
Sat 6/69:00 am
ORD
- SJC
1 stop7h 13m
Alaska Airlines
Deal found 5/7![Alaska Airlines logo]()
$300
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.
Thu 6/42:00 pm
SJC
- ORD
1 stop7h 55m
Multiple Airlines
Thu 6/117:20 am
ORD
- SJC
1 stop7h 57m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$299
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 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
This Expedia 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 Expedia 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
Tue 6/237:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 5/7![Alaska Airlines logo]()
$302
This Frontier deal was found by Cheapflights users on 5/9. 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 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
Mon 6/297:20 am
ORD
- SJC
1 stop7h 57m
Frontier
Deal found 5/9![Frontier logo]()
$290
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 May 10, 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 May 10, 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
Deal found 5/7![Southwest logo]()
$144
This Frontier deal was found by Cheapflights users on 5/9. 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 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 5/9![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 6/152:12 pm
SJC
- ORD
1 stop12h 55m
Frontier
Deal found 5/6![Frontier logo]()
$151
This Booking.com deal was found by Cheapflights users on 5/9. 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 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 5/9![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 United Airlines deal was found by Cheapflights users on 5/9. 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.
Tue 8/182:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 5/9![United Airlines logo]()
$155
This CheapOair deal was found by Cheapflights users on 5/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3012:57 pm
SJC
- ORD
1 stop15h 37m
Frontier
Deal found 5/9![Frontier logo]()
$156
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.
Sat 5/302:00 pm
SJC
- ORD
1 stop7h 55m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$157
This Booking.com deal was found by Cheapflights users on 5/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:57 pm
SJC
- ORD
1 stop15h 22m
Frontier
Deal found 5/10![Frontier logo]()
$158
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 May 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $273 (Expedia) |
One-way from | $144 (Southwest) |
Popular in | November |
Cheapest in | September |
Average price | $371 |
Good round-trip deal | $448 or less |
Good one-way deal | $318 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 2,558,603 searches. Data last updated May 10, 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 - ORD
SJCORD
San Jose
Tue 6/16
1:40 pm-9:57 pm
1 stop6h 17m
Chicago O'Hare Intl
Tue 6/23
7:45 am-12:38 pm
1 stop6h 53m
$277
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 6/2
1:14 pm-10:59 pm
1 stop7h 45m
Chicago O'Hare Intl
Wed 6/3
2:10 pm-7:22 pm
1 stop7h 12m
$277
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 6/8
7:06 am-6:50 pm
1 stop9h 44m
Chicago O'Hare Intl
Sat 6/13
5:59 pm-11:54 pm
1 stop7h 55m
$347
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 7/14
6:37 pm-5:00 am
1 stop8h 23m
Chicago O'Hare Intl
Thu 7/30
6:20 am-11:24 am
1 stop7h 04m
$347
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 6/30
1:40 pm-9:57 pm
1 stop6h 17m
Chicago O'Hare Intl
Fri 7/10
5:30 am-11:30 am
1 stop8h 00m
$352
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 6/9
7:00 am-6:58 pm
2 stops9h 58m
Chicago O'Hare Intl
Fri 6/12
7:45 am-5:17 pm
2 stops11h 32m
$362
San JoseChicago
SJC - ORD
SJCORD
San Jose
Sun 11/1
6:40 am-1:00 pm
Nonstop4h 20m
Chicago O'Hare Intl
Sun 11/8
5:00 am-9:51 am
1 stop6h 51m
$417
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 6/30
6:00 am-4:26 pm
2 stops8h 26m
Chicago O'Hare Intl
Mon 7/6
7:45 am-12:38 pm
1 stop6h 53m
$440
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 9/30
1:05 pm-10:36 pm
1 stop7h 31m
Chicago O'Hare Intl
Thu 10/1
8:00 pm-10:36 pm
Nonstop4h 36m
$442
Quickest round-trip
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 8/26
6:30 am-12:53 pm
Nonstop4h 23m
Chicago O'Hare Intl
Mon 8/31
7:55 pm-10:41 pm
Nonstop4h 46m
$505
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 May.
| 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 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
How far ahead should I book a flight from San Jose, California to Chicago O'Hare Intl Airport?
Booking 3 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, September is the cheapest month in which you can book a flight from San Jose, California to Chicago O'Hare Intl Airport (average of $360). Flying from San Jose, California to Chicago O'Hare Intl Airport in November 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 May 10, 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 May 10, 2026.
Read reviews from past customers who have flown Alaska Airlines,Southwest, 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.
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
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 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 locationsRosemont
Schaumburg
Naperville
Benton Harbor
Delavan
Oakbrook Terrace
Lake Geneva
Gurnee
Downers Grove
Des Plaines
Hoffman Estates
Oak Brook
South Holland
Libertyville
Warrenville
Elk Grove Village
Bridgeview
Great Lakes
Arlington Heights
Northbrook
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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 May 10, 2026.
San Jose and O'Hare Intl flights
Browse other San Jose and O'Hare Intl flight options. Last updated on May 10, 2026.
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Browse through other flights departing from San Jose. Flights are based on user searches made on Cheapflights and were last updated on May 10, 2026.
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Top 7 airlines flying from San Jose to O'Hare Intl
Discover the top 7 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 2,558,603 searches. Data last updated May 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$239 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$294 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$424 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$235 | Average$334 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$236 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$496 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$278 | Average$548 | FlexibilityNo cancel fee | On-time69% |