Flights from San Jose to Chicago

March 2016
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Leaving Thu, Mar 3

Returning options:

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= Cheapest round-trip flights

* Prices are round trip per person (conditions apply)

Selected fares from San Jose to Chicago

Departure
Arrival
Travel dates
Round-trip

Departure:

SJO

Arrival:

CHI

Travel dates

Tue, May 10 - Tue, May 17

Round-trip

Departure:

SJO

Arrival:

CHI

Travel dates

Thu, Feb 25 - Fri, Feb 26

Round-trip

Departure:

SJO

Arrival:

CHI

Travel dates

Sun, Feb 14 - Tue, Feb 23

Round-trip

Departure:

SJO

Arrival:

CHI

Travel dates

Sun, Feb 14 - Tue, Feb 23

Round-trip

Departure:

SJO

Arrival:

CHI

Travel dates

Sun, Feb 14 - Tue, Feb 23

Round-trip

Departure:

SJO

Arrival:

CHI

Travel dates

Tue, Jul 5 - Mon, Jul 11

Round-trip

Save more with Chicago Flight + Hotel packages

San Jose and Chicago airports and terminals

Airports in San Jose , CR

San Jose

Airports in Chicago IL, US

Chicago

  

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Featured Chicago Airport Hotels

http://www.tnetnoc.com/hotelphotos/890/40890/2631759-Hilton-Chicago-OHare-Airport-Hotel-Exterior-1-LP.jpg
O'Hare International Airport Map
3.9 / 5 128 reviews
  • Rate Includes Breakfast
  • Rate Includes Breakfast
From
$79

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

From
$79
http://www.tnetnoc.com/hotelphotos/298/23298/2631759-Holiday-Inn-Express-Suites-CHICAGO-MIDWAY-AIRPORT-Hotel-Exterior-1-LP.jpg
6500 South Cicero Avenue Map
4.1 / 5 43 reviews
From
$120

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

From
$120
http://www.tnetnoc.com/hotelphotos/815/85815/2631759-Hilton-Garden-Inn-ChicagoMidway-Airport-Hotel-Exterior-1-LP.jpg
6530 S. Cicero Avenue Map
3.7 / 5 15 reviews
  • Complimentary wired and Wi-Fi Internet Access
  • Complimentary wired and Wi-Fi Internet Access
From
$118

...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

From
$118
http://www.tnetnoc.com/hotelphotos/232/29232/2631759-Hampton-Inn-Chicago-Midway-Airport-Hotel-Exterior-2-LP.jpg
6540 S. Cicero Ave. Map
3.8 / 5 17 reviews
  • Free On The HouseT hot breakfast, Wi-Fi
  • Free On The HouseT hot breakfast, Wi-Fi
From
$118

...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

From
$118
http://www.tnetnoc.com/hotelphotos/556/170556/2631759-Chicago-Marriott-Midway-Hotel-Exterior-1-LP.jpg
6520 South Cicero Avenue Map
3.7 / 5 7 reviews
  • Rate includes breakfast
  • Rate includes breakfast
From
$159

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

From
$159

March

Cheapest weekend flights in March from San Jose to Chicago

Leave
Fri, Mar 11
San Jose
(SJO)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Sun, Mar 13
Chicago
(ORD)
San Jose
(SJO)
Spirit Airlines
Spirit Airlines
Earn $4.41

Lowest roundtrip airfare in March from San Jose to Chicago

Leave
Thu, Mar 3
San Jose
(SJO)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Tue, Mar 8
Chicago
(ORD)
San Jose
(SJO)
Spirit Airlines
Spirit Airlines
Earn $2.73

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

Leave
Sun, Mar 20
San Jose
(SJO)
Chicago
(ORD)
AeroMexico
AeroMexico
Return
Sun, Mar 27
Chicago
(ORD)
San Jose
(SJO)
AeroMexico
AeroMexico
Earn $6.05

April

Cheapest weekend flights in April from San Jose to Chicago

Leave
Thu, Apr 7
San Jose
(SJO)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Sun, Apr 10
Chicago
(ORD)
San Jose
(SJO)
Spirit Airlines
Spirit Airlines
Earn $3.57

Lowest roundtrip airfare in April from San Jose to Chicago

Leave
Tue, Apr 12
San Jose
(SJO)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Tue, Apr 26
Chicago
(ORD)
San Jose
(SJO)
Spirit Airlines
Spirit Airlines
Earn $2.73

May

Lowest roundtrip airfare in May from San Jose to Chicago

Leave
Wed, May 11
San Jose
(SJO)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Tue, May 17
Chicago
(ORD)
San Jose
(SJO)
Spirit Airlines
Spirit Airlines
Earn $2.73

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

Leave
Tue, May 10
San Jose
(SJO)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Tue, May 17
Chicago
(ORD)
San Jose
(SJO)
Spirit Airlines
Spirit Airlines
Earn $2.73

San Jose to Chicago Intro 3

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