Flights from San Jose to Chicago

Selected fares from San Jose to Chicago

Departure Arrival Travel dates Round-trip
SJO CHI Thu, Oct 8 - Wed, Oct 14 $463
SJO CHI Mon, May 11 - Tue, May 12 $568
SJO CHI Sat, Jul 11 - Sat, Jul 18 $650
SJO CHI Thu, May 14 - Mon, May 18 $664
SJO CHI Thu, May 14 - Mon, May 18 $679
SJO CHI Wed, Dec 23 - Wed, Jan 13 $690
SJO CHI Thu, Oct 8 - Wed, Oct 14 $722
SJO CHI Thu, May 14 - Mon, May 18 $732
SJO CHI Thu, May 14 - Mon, May 18 $732
SJO CHI Wed, Dec 23 - Wed, Jan 13 $801

San Jose and Chicago airports and terminals

Airports in San Jose , CR

map of airports in San Jose
  • 1

    Juan Santamaria Intl (SJO)

    Distance from City Center: 10 miles

    Terminals and carriers for flights from SJO to CHI

    Terminal Carriers
    Terminal M United Airlines
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Airports in Chicago IL, US

map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from SJO to ORD

    Terminal Carriers
    Terminal 5 United Airlines
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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $79

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 128 reviews

O'Hare International Airport Map

Rate Includes Breakfast

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Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 43 reviews

6500 South Cicero Avenue Map

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Hilton Garden Inn Chicago/Midway Airport

3 stars
3.7 / 5 15 reviews

6530 S. Cicero Avenue Map

Complimentary wired and Wi-Fi Internet Access

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Hotel only $118

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 17 reviews

6540 S. Cicero Ave. Map

Free On The HouseT hot breakfast, Wi-Fi

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $159

Chicago Marriott Midway

3 stars
3.7 / 5 7 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

Perfect for business travel and weekend getaways, the renovated Marriott Chicago Midway is just two blocks from MDW airport and offers a free 24-hr shuttle.... More

June

Cheapest weekend flights in June from San Jose to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jun 11 San Jose (SJO) Chicago (ORD) Spirit Airlines $509
Earn $5.09
Return Mon, Jun 15 Chicago (ORD) San Jose (SJO) Spirit Airlines

Lowest roundtrip airfare in June from San Jose to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jun 6 San Jose (SJO) Chicago (ORD) Spirit Airlines $448
Earn $4.48
Return Tue, Jul 7 Chicago (ORD) San Jose (SJO) Spirit Airlines

Best one-week trip in June from San Jose to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jun 13 San Jose (SJO) Chicago (ORD) Spirit Airlines $505
Earn $5.05
Return Sat, Jun 20 Chicago (ORD) San Jose (SJO) Spirit Airlines
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July

Lowest roundtrip airfare in July from San Jose to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jul 30 San Jose (SJO) Chicago (ORD) Spirit Airlines $505
Earn $5.05
Return Sun, Aug 30 Chicago (ORD) San Jose (SJO) Spirit Airlines

Best one-week trip in July from San Jose to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jul 11 San Jose (SJO) Chicago (ORD) Spirit Airlines $516
Earn $5.16
Return Sat, Jul 18 Chicago (ORD) San Jose (SJO) Spirit Airlines
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San Jose to Chicago Intro 12

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Flight schedule for flights from San Jose to Chicago on Mon, May 4, 2015

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
British Airways/British Airways BA5340/BA1636 SJO 6:26 AM ORD 4:18 PM 757/738 8hr 52min
British Airways/British Airways BA5100/BA4496 SJO 7:40 AM ORD 6:54 PM 757/M80 10hr 14min
American Airlines/American Airlines AA2444/AA314 SJO 1:10 PM ORD 10:22 PM 738/738 8hr 12min
American Airlines/US Airways AA2444/US314 SJO 1:10 PM ORD 10:22 PM 738/738 8hr 12min
US Airways/American Airlines US2444/AA314 SJO 1:10 PM ORD 10:22 PM 738/738 8hr 12min
US Airways/US Airways US2444/US314 SJO 1:10 PM ORD 10:22 PM 738/738 8hr 12min
American Airlines/American Airlines AA1706/AA1788 SJO 2:35 PM ORD 11:21 PM 319/757 7hr 46min
American Airlines/US Airways AA1706/US1788 SJO 2:35 PM ORD 11:21 PM 319/752 7hr 46min
US Airways/American Airlines US1706/AA1788 SJO 2:35 PM ORD 11:21 PM 319/757 7hr 46min
US Airways/US Airways US1706/US1788 SJO 2:35 PM ORD 11:21 PM 319/752 7hr 46min
American Airlines/American Airlines AA2444/AA1065 SJO 1:10 PM ORD 11:51 PM 738/738 9hr 41min
American Airlines/US Airways AA2444/US1065 SJO 1:10 PM ORD 11:51 PM 738/738 9hr 41min
US Airways/American Airlines US2444/AA1065 SJO 1:10 PM ORD 11:51 PM 738/738 9hr 41min