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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

January
February
March
April
August
September
October
November
December

January 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

06:15

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri , 30 Jan 2026

07h 20m
ellipse
1 Stop

Chicago

13:35

Chicago O Hare International Airport [ORD]

Fri, 30 Jan 2026

$166
United Airlines
United Airlines

Winnipeg

14:20

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri , 30 Jan 2026

02h 43m
ellipse
Non Stop

Chicago

17:03

Chicago O Hare International Airport [ORD]

Fri, 30 Jan 2026

$274
Air Canada
Air Canada

Winnipeg

05:30

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri , 30 Jan 2026

07h 31m
ellipse
1 Stop

Chicago

13:01

Chicago O Hare International Airport [ORD]

Fri, 30 Jan 2026

$288
Air Canada
Air Canada

Winnipeg

14:20

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri , 30 Jan 2026

02h 43m
ellipse
Non Stop

Chicago

17:03

Chicago O Hare International Airport [ORD]

Fri, 30 Jan 2026

$301
Porter Airlines
Porter Airlines

Winnipeg

12:10

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri , 30 Jan 2026

07h 54m
ellipse
1 Stop

Chicago

20:04

Chicago O Hare International Airport [ORD]

Fri, 30 Jan 2026

$315
American Airlines
American Airlines

Winnipeg

12:10

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri , 30 Jan 2026

07h 54m
ellipse
1 Stop

Chicago

20:04

Chicago O Hare International Airport [ORD]

Fri, 30 Jan 2026

$339
United Airlines
United Airlines

Winnipeg

14:20

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 02 Feb 2026

02h 43m
ellipse
Non Stop

Chicago

17:03

Chicago O Hare International Airport [ORD]

Mon, 02 Feb 2026

$519
Porter Airlines
Porter Airlines

Winnipeg

12:10

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 02 Feb 2026

07h 54m
ellipse
1 Stop

Chicago

20:04

Chicago O Hare International Airport [ORD]

Mon, 02 Feb 2026

$534
Air Canada
Air Canada

Winnipeg

07:05

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 02 Feb 2026

05h 56m
ellipse
1 Stop

Chicago

13:01

Chicago O Hare International Airport [ORD]

Mon, 02 Feb 2026

$536
Porter Airlines
Porter Airlines

Winnipeg

06:00

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 02 Feb 2026

06h 30m
ellipse
1 Stop

Chicago

12:30

Chicago O Hare International Airport [ORD]

Mon, 02 Feb 2026

$699
WestJet Airlines
WestJet Airlines

Winnipeg

05:00

Winnipeg James Armstrong Richardson International Airport [YWG]

Fri , 30 Jan 2026

07h 08m
ellipse
1 Stop

Chicago

12:08

Chicago O Hare International Airport [ORD]

Fri, 30 Jan 2026

$891
ellipse

Early Morning Flight Winnipeg to Chicago

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Cheapest Flight
Found
$891
group
Average Flight
Time
07h 08m
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Date/Time
30 Jan 2026
05:00 AM
plane
Airlines
WestJet Airlines
Ellipse

Late Night Flight Winnipeg to Chicago

wallet
Cheapest Flight
Found
$274
group
Average Flight
Time
02h 43m
calendar
Date/Time
30 Jan 2026
14:20 PM
plane
Airlines
United Airlines