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Winnipeg 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

April
August
September
October
November
December
January
February
March

April is by far the best month, wherein you can get cheapest flights for Winnipeg 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 Winnipeg To Chicago

WestJet Airlines
WestJet Airlines

Winnipeg

07:00

Winnipeg James Armstrong Richardson International Airport [YWG]

Thu , 30 Apr 2026

09h 40m
ellipse
1 Stop

Chicago

16:40

Chicago O Hare International Airport [ORD]

Thu, 30 Apr 2026

$157
Porter Airlines
Porter Airlines

Winnipeg

12:10

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 06 Apr 2026

07h 07m
ellipse
1 Stop

Chicago

19:17

Chicago O Hare International Airport [ORD]

Mon, 06 Apr 2026

$217
Porter Airlines
Porter Airlines

Winnipeg

06:00

Winnipeg James Armstrong Richardson International Airport [YWG]

Sat , 11 Apr 2026

06h 43m
ellipse
1 Stop

Chicago

12:43

Chicago O Hare International Airport [ORD]

Sat, 11 Apr 2026

$217
Air Canada
Air Canada

Winnipeg

13:30

Winnipeg James Armstrong Richardson International Airport [YWG]

Sat , 11 Apr 2026

05h 55m
ellipse
1 Stop

Chicago

19:25

Chicago O Hare International Airport [ORD]

Sat, 11 Apr 2026

$313
United Airlines
United Airlines

Winnipeg

14:00

Winnipeg James Armstrong Richardson International Airport [YWG]

Thu , 30 Apr 2026

02h 35m
ellipse
Non Stop

Chicago

16:35

Chicago O Hare International Airport [ORD]

Thu, 30 Apr 2026

$323
United Airlines
United Airlines

Winnipeg

14:00

Winnipeg James Armstrong Richardson International Airport [YWG]

Sat , 11 Apr 2026

02h 35m
ellipse
Non Stop

Chicago

16:35

Chicago O Hare International Airport [ORD]

Sat, 11 Apr 2026

$323
Air Canada
Air Canada

Winnipeg

07:05

Winnipeg James Armstrong Richardson International Airport [YWG]

Thu , 30 Apr 2026

06h 00m
ellipse
1 Stop

Chicago

13:05

Chicago O Hare International Airport [ORD]

Thu, 30 Apr 2026

$327
Air Canada
Air Canada

Winnipeg

13:30

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 06 Apr 2026

05h 55m
ellipse
1 Stop

Chicago

19:25

Chicago O Hare International Airport [ORD]

Mon, 06 Apr 2026

$336
Porter Airlines
Porter Airlines

Winnipeg

12:10

Winnipeg James Armstrong Richardson International Airport [YWG]

Thu , 30 Apr 2026

07h 22m
ellipse
1 Stop

Chicago

19:32

Chicago O Hare International Airport [ORD]

Thu, 30 Apr 2026

$353
American Airlines
American Airlines

Winnipeg

06:00

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 06 Apr 2026

06h 35m
ellipse
1 Stop

Chicago

12:35

Chicago O Hare International Airport [ORD]

Mon, 06 Apr 2026

$356
WestJet Airlines
WestJet Airlines

Winnipeg

06:15

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 06 Apr 2026

07h 20m
ellipse
1 Stop

Chicago

13:35

Chicago O Hare International Airport [ORD]

Mon, 06 Apr 2026

$356
ellipse

Early Morning Flight Winnipeg to Chicago

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Cheapest Flight
Found
$356
group
Average Flight
Time
06h 35m
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Date/Time
06 Apr 2026
06:00 AM
plane
Airlines
American Airlines
Ellipse

Late Night Flight Winnipeg to Chicago

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Cheapest Flight
Found
$323
group
Average Flight
Time
02h 35m
calendar
Date/Time
11 Apr 2026
14:00 PM
plane
Airlines
United Airlines