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San Jose To Chicago Flights

  • One-Way
  • Round-Trip
  • Multi-City

From

Indira Gandhi International Airport

To

Chhatrapati Shivaji International Airport

DEPARTURE DATE

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Friday

Return Date

Book a round trip
to save more

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TRAVELLER & CLASS

1 Traveller

Economy

November
December
January
February
March
April
August
September
October

November is by far the best month, wherein you can get cheapest flights for San Jose to Chicago. Meanwhile, is perceived as the expensive month due to the varying factors. That’s why it’s highly advised to make advanced online flight booking to save huge amounts of money.

disclDisclaimer - All the mentioned fares were found within last 48 hrs. The displayed fares are based on historical data and are subject to change. The fares cannot be guaranteed at the time of booking.

Best Flight From San Jose To Chicago

Cheapest
Hawaiian Airlines
Hawaiian Airlines

SJC

19:47

San Jose Norman Y Mineta San Jose International Airport

Mon , 17 Nov 2025

08h 35m
ellipse
1 Stop

ORD

06:22

Chicago Chicago O Hare International Airport

Tue, 18 Nov 2025

$227
Alaska Airlines
Alaska Airlines

SJC

15:00

San Jose Norman Y Mineta San Jose International Airport

Tue , 18 Nov 2025

06h 59m
ellipse
1 Stop

ORD

23:59

Chicago Chicago O Hare International Airport

Tue, 18 Nov 2025

$270
Hawaiian Airlines
Hawaiian Airlines

SJC

15:00

San Jose Norman Y Mineta San Jose International Airport

Tue , 18 Nov 2025

06h 59m
ellipse
1 Stop

ORD

23:59

Chicago Chicago O Hare International Airport

Tue, 18 Nov 2025

$270
Alaska Airlines
Alaska Airlines

SJC

15:00

San Jose Norman Y Mineta San Jose International Airport

Mon , 17 Nov 2025

06h 59m
ellipse
1 Stop

ORD

23:59

Chicago Chicago O Hare International Airport

Mon, 17 Nov 2025

$279
Hawaiian Airlines
Hawaiian Airlines

SJC

15:00

San Jose Norman Y Mineta San Jose International Airport

Mon , 17 Nov 2025

06h 59m
ellipse
1 Stop

ORD

23:59

Chicago Chicago O Hare International Airport

Mon, 17 Nov 2025

$279
Alaska Airlines
Alaska Airlines

SJC

15:00

San Jose Norman Y Mineta San Jose International Airport

Sun , 16 Nov 2025

06h 59m
ellipse
1 Stop

ORD

23:59

Chicago Chicago O Hare International Airport

Sun, 16 Nov 2025

$513
United Airlines
United Airlines

SJC

06:30

San Jose Norman Y Mineta San Jose International Airport

Sun , 23 Nov 2025

04h 20m
ellipse
Non Stop

ORD

12:50

Chicago Chicago O Hare International Airport

Sun, 23 Nov 2025

$771
United Airlines
United Airlines

SJC

06:30

San Jose Norman Y Mineta San Jose International Airport

Thu , 20 Nov 2025

04h 20m
ellipse
Non Stop

ORD

12:50

Chicago Chicago O Hare International Airport

Thu, 20 Nov 2025

$779
United Airlines
United Airlines

SJC

06:30

San Jose Norman Y Mineta San Jose International Airport

Sat , 22 Nov 2025

04h 22m
ellipse
Non Stop

ORD

12:52

Chicago Chicago O Hare International Airport

Sat, 22 Nov 2025

$1036
ellipse

Early Morning Flight San Jose to Chicago

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Cheapest Flight
Found
$779
group
Average Flight
Time
04h 20m
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Date/Time
20 Nov 2025
06:30 AM
plane
Airlines
United Airlines
Ellipse

Late Night Flight San Jose to Chicago

wallet
Cheapest Flight
Found
$227
group
Average Flight
Time
08h 35m
calendar
Date/Time
17 Nov 2025
19:47 PM
plane
Airlines
Hawaiian Airlines