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San Jose to Chicago Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from San Jose to Chicago

Departure Arrival Travel dates Round-trip
SJO CHI Fri, Oct 10 - Sun, Oct 12 $355
SJO CHI Thu, Sep 18 - Mon, Sep 22 $512
SJO CHI Thu, Sep 18 - Mon, Sep 22 $541
SJO CHI Thu, Sep 18 - Mon, Sep 22 $544
SJO CHI Sat, Sep 27 - Sun, Oct 5 $553
SJO CHI Fri, Sep 26 - Wed, Oct 8 $614
SJO CHI Tue, Sep 16 - Thu, Oct 16 $663
SJO CHI Thu, Aug 14 - Thu, Aug 21 $664
SJO CHI Fri, Nov 21 - Tue, Dec 2 $803
SJO CHI Fri, Nov 21 - Tue, Dec 2 $855

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 1 United Airlines
    Terminal 5 United Airlines
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Cheap flights from San Jose to Chicago

Sun Mon Tue Wed Thu Fri Sat
1 2
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24 25 26 27
$357
28 29 30
31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $139

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 165 reviews

O'Hare International Airport Map

Park & Fly - Includes up to 3 nights valet parking

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 68 reviews

6500 SOUTH CICERO AVE Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $144

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.6 / 5 22 reviews

6530 S. Cicero Avenue Map

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $135

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 30 reviews

6540 S. Cicero Ave. Map

...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 $179

Chicago Marriott Midway

3 stars
3.6 / 5 11 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

...WiFi-equipped guest rooms at our Chicago Midway Airport hotel are recently renovated and offer soundproof windows, 32" flat-screen TVs and room service.... Perfect for business travel and... More

Hotel only $99

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 147 reviews

6501 N. Mannheim Road Map

Save 40% on your stay

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

August

Cheapest weekend flights in August from San Jose to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Aug 8 San Jose (SJO) Chicago (ORD) Spirit Airlines $551
Earn $5.51
Return Mon, Aug 11 Chicago (ORD) San Jose (SJO) Spirit Airlines

Lowest roundtrip airfare in August from San Jose to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Aug 27 San Jose (SJO) Chicago (ORD) Spirit Airlines $357
Earn $3.57
Return Wed, Sep 3 Chicago (ORD) San Jose (SJO) Spirit Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Aug 27 San Jose (SJO) Chicago (ORD) Spirit Airlines $357
Earn $3.57
Return Wed, Sep 3 Chicago (ORD) San Jose (SJO) Spirit Airlines
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September

Cheapest weekend flights in September from San Jose to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 18 San Jose (SJO) Chicago (ORD) Spirit Airlines $357
Earn $3.57
Return Mon, Sep 22 Chicago (ORD) San Jose (SJO) Spirit Airlines

Lowest roundtrip airfare in September from San Jose to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Sep 10 San Jose (SJO) Chicago (ORD) Spirit Airlines $357
Earn $3.57
Return Thu, Oct 16 Chicago (ORD) San Jose (SJO) Spirit Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Sep 9 San Jose (SJO) Chicago (ORD) Spirit Airlines $357
Earn $3.57
Return Tue, Sep 16 Chicago (ORD) San Jose (SJO) Spirit Airlines
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October

Cheapest weekend flights in October from San Jose to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Oct 17 San Jose (SJO) Chicago (ORD) Spirit Airlines $355
Earn $3.55
Return Sun, Oct 19 Chicago (ORD) San Jose (SJO) Spirit Airlines

Lowest roundtrip airfare in October from San Jose to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Oct 17 San Jose (SJO) Chicago (ORD) Spirit Airlines $355
Earn $3.55
Return Sun, Oct 19 Chicago (ORD) San Jose (SJO) Spirit Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 9 San Jose (SJO) Chicago (ORD) Spirit Airlines $357
Earn $3.57
Return Thu, Oct 16 Chicago (ORD) San Jose (SJO) Spirit Airlines
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San Jose to Chicago Intro 30

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Aircraft options between San Jose and Chicago

Equipment Carrier
Boeing 737-800 Passenger United Airlines