Winnipeg To Chicago Flights

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

From

Indira Gandhi International Airport

To

Chhatrapati Shivaji International Airport

DEPARTURE DATE

calender

Friday

Return Date

Book a round trip
to save more

calender

TRAVELLER & CLASS

1 Traveller

Economy

August
September
October
November
December
January
February
March
April

June 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

Air Canada
Air Canada

Winnipeg

15:20

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 29 Jun 2026

06h 45m
ellipse
1 Stop

Chicago

22:05

Chicago O Hare International Airport [ORD]

Mon, 29 Jun 2026

$403
Air Canada
Air Canada

Winnipeg

05:10

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 29 Jun 2026

06h 11m
ellipse
1 Stop

Chicago

11:21

Chicago O Hare International Airport [ORD]

Mon, 29 Jun 2026

$431
United Airlines
United Airlines

Winnipeg

05:10

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 29 Jun 2026

06h 11m
ellipse
1 Stop

Chicago

11:21

Chicago O Hare International Airport [ORD]

Mon, 29 Jun 2026

$433
WestJet Airlines
WestJet Airlines

Winnipeg

06:40

Winnipeg James Armstrong Richardson International Airport [YWG]

Tue , 30 Jun 2026

04h 51m
ellipse
1 Stop

Chicago

11:31

Chicago O Hare International Airport [ORD]

Tue, 30 Jun 2026

$471
United Airlines
United Airlines

Winnipeg

07:00

Winnipeg James Armstrong Richardson International Airport [YWG]

Tue , 30 Jun 2026

02h 34m
ellipse
Non Stop

Chicago

09:34

Chicago O Hare International Airport [ORD]

Tue, 30 Jun 2026

$489
Delta Airlines
Delta Airlines

Winnipeg

12:46

Winnipeg James Armstrong Richardson International Airport [YWG]

Tue , 30 Jun 2026

04h 16m
ellipse
1 Stop

Chicago

17:02

Chicago O Hare International Airport [ORD]

Tue, 30 Jun 2026

$504
American Airlines
American Airlines

Winnipeg

20:45

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 29 Jun 2026

11h 50m
ellipse
1 Stop

Chicago

08:35

Chicago O Hare International Airport [ORD]

Tue, 30 Jun 2026

$504
United Airlines
United Airlines

Winnipeg

05:10

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 29 Jun 2026

08h 12m
ellipse
1 Stop

Chicago

13:22

Chicago O Hare International Airport [ORD]

Mon, 29 Jun 2026

$523
WestJet Airlines
WestJet Airlines

Winnipeg

07:00

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 29 Jun 2026

09h 40m
ellipse
1 Stop

Chicago

16:40

Chicago O Hare International Airport [ORD]

Mon, 29 Jun 2026

$539
Air Canada
Air Canada

Winnipeg

07:00

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 29 Jun 2026

02h 34m
ellipse
Non Stop

Chicago

09:34

Chicago O Hare International Airport [ORD]

Mon, 29 Jun 2026

$556
Delta Airlines
Delta Airlines

Winnipeg

12:46

Winnipeg James Armstrong Richardson International Airport [YWG]

Mon , 29 Jun 2026

04h 16m
ellipse
1 Stop

Chicago

17:02

Chicago O Hare International Airport [ORD]

Mon, 29 Jun 2026

$675
ellipse

Early Morning Flight Winnipeg to Chicago

wallet
Cheapest Flight
Found
$431
group
Average Flight
Time
06h 11m
calendra
Date/Time
29 Jun 2026
05:10 AM
plane
Airlines
Air Canada
Ellipse

Late Night Flight Winnipeg to Chicago

wallet
Cheapest Flight
Found
$403
group
Average Flight
Time
06h 45m
calendar
Date/Time
29 Jun 2026
15:20 PM
plane
Airlines
Air Canada