One Way

Popular Filters

+ 1 more

One Way Price

KWD 131 KWD 400

Duration

2 h 31 m 29 h 30 m

Stops From Winnipeg

Departure From Winnipeg

Before 6 AM

KWD 145.09

6 AM - 12 PM

KWD 131.09

12 PM - 6 PM

KWD 131.09

After 6 PM

KWD 145.09

Arrival at Chicago

6 AM - 12 PM

KWD 145.09

12 PM - 6 PM

KWD 131.09

After 6 PM

KWD 131.09

Alliances & Airlines

Oneworld

(1)

SkyTeam

(10)

Star Alliance

(38)

Layover Airports

+ 4 more

Layover Duration

39 m 24 h 0 m

Winnipeg To Chicago Flights

Book Winnipeg to Chicago flight tickets at lowest price. Get best deals on your upcoming Winnipeg to Chicago flights only on MakeMyTrip. Also Book Chicago to Winnipeg Flights. Currently 60 flights flying from Winnipeg to Chicago. To save maximum on flight booking click on below Fare Calendar button and choose your dates.

Sorted By:
Departure
Duration
Arrival
Price
WestJet

More Timing Options

KWD 134

KWD 131.09

Winnipeg to Chicago , 30 Sep

WestJet WS | 6333 | Operated By Delta Air Lines

06:40

Tue, 30 Sep 25

Winnipeg, Canada

01 h 34 m

08:14

Tue, 30 Sep 25

Terminal T1

Minneapolis, United States

BAGGAGE : CHECK INCABIN

Information not available

WestJet WS | 8204 | Operated By Delta Air Lines

10:30

Tue, 30 Sep 25

Terminal T1

Minneapolis, United States

01 h 30 m

12:00

Tue, 30 Sep 25

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

WestJet

KWD 140

KWD 137.09

Winnipeg to Chicago-Midway , 30 Sep

WestJet WS | 546

10:45

Tue, 30 Sep 25

Winnipeg, Canada

02 h 27 m

14:12

Tue, 30 Sep 25

Terminal T3

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

WestJet WS | 6767 | Operated By Delta Air Lines

16:12

Tue, 30 Sep 25

Terminal T3

Toronto, Canada

01 h 19 m

17:31

Tue, 30 Sep 25

Terminal M

Detroit, United States

BAGGAGE : CHECK INCABIN

Information not available

WestJet WS | 7056 | Operated By Delta Air Lines

18:20

Tue, 30 Sep 25

Terminal M

Detroit, United States

01 h 15 m

18:35

Tue, 30 Sep 25

Chicago-Midway, United States

BAGGAGE : CHECK INCABIN

Information not available

United Airlines

More Timing Options

KWD 148

KWD 145.09

Winnipeg to Chicago , 30 Sep

United Airlines UA | 8444 | Operated By Air Canada

05:00

Tue, 30 Sep 25

Winnipeg, Canada

02 h 25 m

08:25

Tue, 30 Sep 25

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

United Airlines UA | 3605

13:00

Tue, 30 Sep 25

Terminal T1

Toronto, Canada

02 h 01 m

14:01

Tue, 30 Sep 25

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Air Canada

More Timing Options

KWD 150

KWD 147.09

Winnipeg to Chicago , 30 Sep

Air Canada AC | 4135 | Operated By United Airlines

07:00

Tue, 30 Sep 25

Winnipeg, Canada

02 h 31 m

09:31

Tue, 30 Sep 25

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines

More Timing Options

KWD 151

KWD 148.09

Winnipeg to Chicago , 30 Sep

Delta Air Lines DL | 3660

06:40

Tue, 30 Sep 25

Winnipeg, Canada

01 h 34 m

08:14

Tue, 30 Sep 25

Terminal T1

Minneapolis, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL | 1567

10:30

Tue, 30 Sep 25

Terminal T1

Minneapolis, United States

01 h 30 m

12:00

Tue, 30 Sep 25

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines

More Timing Options

KWD 152

KWD 149.09

Winnipeg to Chicago , 30 Sep

Delta Air Lines DL | 3526

08:35

Tue, 30 Sep 25

Winnipeg, Canada

01 h 34 m

10:09

Tue, 30 Sep 25

Terminal T1

Minneapolis, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL | 1533

13:28

Tue, 30 Sep 25

Terminal T1

Minneapolis, United States

01 h 33 m

15:01

Tue, 30 Sep 25

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Air Canada

More Timing Options

KWD 153

KWD 150.09

Winnipeg to Chicago , 30 Sep

Air Canada AC | 256

05:00

Tue, 30 Sep 25

Winnipeg, Canada

02 h 25 m

08:25

Tue, 30 Sep 25

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC | 8903

10:00

Tue, 30 Sep 25

Terminal T1

Toronto, Canada

01 h 53 m

10:53

Tue, 30 Sep 25

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Air Canada

More Timing Options

KWD 159

KWD 156.09

Winnipeg to Chicago , 30 Sep

Air Canada AC | 256

05:00

Tue, 30 Sep 25

Winnipeg, Canada

02 h 25 m

08:25

Tue, 30 Sep 25

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC | 5588 | Operated By United Airlines

13:00

Tue, 30 Sep 25

Terminal T1

Toronto, Canada

02 h 01 m

14:01

Tue, 30 Sep 25

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

WestJet

KWD 174

KWD 171.09

Winnipeg to Chicago , 30 Sep

WestJet WS | 261

08:30

Tue, 30 Sep 25

Winnipeg, Canada

02 h 14 m

09:44

Tue, 30 Sep 25

Calgary, Canada

BAGGAGE : CHECK INCABIN

Information not available

WestJet WS | 1588

12:15

Tue, 30 Sep 25

Calgary, Canada

03 h 28 m

16:43

Tue, 30 Sep 25

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

WestJet

KWD 183

KWD 180.09

Winnipeg to Chicago , 30 Sep

WestJet WS | 223

06:30

Tue, 30 Sep 25

Winnipeg, Canada

02 h 14 m

07:44

Tue, 30 Sep 25

Calgary, Canada

BAGGAGE : CHECK INCABIN

Information not available

WestJet WS | 1588

12:15

Tue, 30 Sep 25

Calgary, Canada

03 h 28 m

16:43

Tue, 30 Sep 25

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Winnipeg to Chicago Flights Information:-

Looking for Winnipeg to Chicago Flight? Hereโ€™s all you need to know! For convenience and to save time, pick the airport that is closest to your destination. The nearest airport to Chicago is Chicago Midway Intl and the IATA code for the same is CHI.
Currently, there are 6 airlines operating flights between the two destinations and approximately 60 flights take off from Winnipeg to Chicago every week.

Need information on Winnipeg to Chicago airfare?

The minimum airfare for a Winnipeg to Chicago flight would be 131, which may go up to 340 depending on the route, booking time and availability.
It is recommended that you book a round-trip, since it always works out to be more economical.

Flight Details for Winnipeg to Chicago

If you are looking for Winnipeg to Chicago flights, there is no dearth of options to choose from. Several reputed airlines currently offer both direct and indirect flights between the two destinations. Some of these are Air Canada, Alaska Airlines, Delta Air Lines, Porter Airlines, United Airlines, WestJet. Out of these, only 4 airlines operate direct flights. Indirect flights may involve more travel time, but they usually cost lesser than direct flights.

The number of flights operated by each airline is as follows:Air Canada : 19, Alaska Airlines : 19, Delta Air Lines : 19, Porter Airlines : 19, United Airlines : 19, WestJet : 19

To board the first Winnipeg to Chicago flight, choose United Airlines, which departs at 05:00 The last flight for this route is Air Canada, departing at 20:10

Chicago Airport Information

Chicago Midway Intl

About Winnipeg (YWG)

Winnipeg

Winnipeg Address

About Chicago (CHI)

The most populous city in the U.S. State of Illinois and the third most populous city in United States, Chicago is the city full of glittering lights and joyous atmosphere. It is a huge vibrant city with metropolitan luxuries of theater, shopping and fine dining. Chicago is one of the world's great cities with the asset of iconic sights and neighborhoods. The meaning of Chicago is found in movement through elevated tracks and subways, in the honor of tired feet and eyes raised once more towards the sky. It is a city full of world-class museums of art and science, sandy beaches, huge parks, public art and one of the finest collections of architectures in the entire world. The Adler Planetarium has all the information for space and astronomy, the Field Museum of Natural History has all the information of Egyptian treasures and Shedd Aquarium has the best collection of marine life, together called as Museum campus is one the most beautiful spot along the lake. The Art Institute of Chicago has an exclusive collection of Impressions, modern and classical art, and tons of historical artifacts. It is a place of beaches and waterfront parks where you can go for a quite picnic and enjoy the calm and peaceful evening away from the crowded city. It is a delightful snow-filled wonderland and even referred to as a very passionate sports town. Chicago is a place for shoppers where you can buy things on a budget or in luxury. The most famous shopping street is The Magnificent Mile which includes designer boutiques and multi-storey malls. State Street is great for department stores. It is one of the great restaurant towns and you can find every cuisine which reflects the city's ethnic and working class roots. It is a major transport hub and has the third largest inter-modal port. Start planning your trip and get your tickets booked from MakeMyTrip.com. The website offers you with a host of services such as hotel deals, flight deals and holiday packages. You have the freedom to book cheap air tickets and hotels to any destinations in the world according to your budget and need.

Chicago Address