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Chicago To Winnipeg 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

January
February
March
April
August
September
October
November
December

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

Air Canada
Air Canada

Chicago

14:00

Chicago O Hare International Airport [ORD]

Thu , 22 Jan 2026

05h 34m
ellipse
1 Stop

Winnipeg

19:34

Winnipeg James Armstrong Richardson International Airport [YWG]

Thu, 22 Jan 2026

$264
WestJet Airlines
WestJet Airlines

Chicago

14:20

Chicago O Hare International Airport [ORD]

Fri , 23 Jan 2026

08h 21m
ellipse
1 Stop

Winnipeg

22:41

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri, 23 Jan 2026

$268
United Airlines
United Airlines

Chicago

09:10

Chicago O Hare International Airport [ORD]

Thu , 22 Jan 2026

02h 47m
ellipse
Non Stop

Winnipeg

11:57

Winnipeg James Armstrong Richardson International Airport [YWG]

Thu, 22 Jan 2026

$321
Porter Airlines
Porter Airlines

Chicago

08:07

Chicago O Hare International Airport [ORD]

Thu , 22 Jan 2026

07h 23m
ellipse
1 Stop

Winnipeg

15:30

Winnipeg James Armstrong Richardson International Airport [YWG]

Thu, 22 Jan 2026

$337
Air Canada
Air Canada

Chicago

09:10

Chicago O Hare International Airport [ORD]

Thu , 22 Jan 2026

02h 47m
ellipse
Non Stop

Winnipeg

11:57

Winnipeg James Armstrong Richardson International Airport [YWG]

Thu, 22 Jan 2026

$359
Porter Airlines
Porter Airlines

Chicago

08:07

Chicago O Hare International Airport [ORD]

Mon , 26 Jan 2026

07h 23m
ellipse
1 Stop

Winnipeg

15:30

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon, 26 Jan 2026

$609
Porter Airlines
Porter Airlines

Chicago

08:07

Chicago O Hare International Airport [ORD]

Fri , 23 Jan 2026

07h 23m
ellipse
1 Stop

Winnipeg

15:30

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri, 23 Jan 2026

$614
United Airlines
United Airlines

Chicago

09:10

Chicago O Hare International Airport [ORD]

Mon , 26 Jan 2026

02h 47m
ellipse
Non Stop

Winnipeg

11:57

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon, 26 Jan 2026

$628
Air Canada
Air Canada

Chicago

09:10

Chicago O Hare International Airport [ORD]

Fri , 23 Jan 2026

02h 47m
ellipse
Non Stop

Winnipeg

11:57

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri, 23 Jan 2026

$747
United Airlines
United Airlines

Chicago

09:10

Chicago O Hare International Airport [ORD]

Fri , 23 Jan 2026

02h 47m
ellipse
Non Stop

Winnipeg

11:57

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri, 23 Jan 2026

$768
American Airlines
American Airlines

Chicago

15:37

Chicago O Hare International Airport [ORD]

Fri , 23 Jan 2026

07h 58m
ellipse
1 Stop

Winnipeg

23:35

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri, 23 Jan 2026

$854
ellipse

Early Morning Flight Chicago to Winnipeg

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Cheapest Flight
Found
$337
group
Average Flight
Time
07h 23m
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Date/Time
22 Jan 2026
08:07 AM
plane
Airlines
Porter Airlines
Ellipse

Late Night Flight Chicago to Winnipeg

wallet
Cheapest Flight
Found
$268
group
Average Flight
Time
08h 21m
calendar
Date/Time
23 Jan 2026
14:20 PM
plane
Airlines
WestJet Airlines