One Way
Lowest Fare Finder Chrome Extension

Popular Filters

+ 1 more

One Way Price

AED 1,455 AED 3,900

Duration

2 h 28 m 22 h 0 m

Stops From Winnipeg

Departure From Winnipeg

6 AM - 12 PM

AED 1,609

12 PM - 6 PM

AED 1,604

After 6 PM

AED 1,455

Arrival at Chicago

6 AM - 12 PM

AED 1,623

12 PM - 6 PM

AED 1,604

After 6 PM

AED 1,455

Alliances & Airlines

Oneworld

()

SkyTeam

(25)

Star Alliance

(41)

Layover Airports

+ 3 more

Layover Duration

41 m 13 h 30 m

Winnipeg to Chicago Flight @AED 1495, Up To 20% Off

Book Winnipeg to Chicago flight tickets at lowest price. Get best deals on your upcoming Winnipeg to Chicago flight only on MakeMyTrip. Also book Chicago to Winnipeg Flight. Currently 69 flights flying from Winnipeg to Chicago. To save maximum on flight booking click on below Fare Calendar button and choose your dates. Use coupon code : “FLYAE” and Get Up To AED 150 OFF* on your flight booking with MakeMyTrip. 100% Refund on Flight cancellations with MMT Zero Cancellation.

Sorted By:
Departure
Duration
Arrival
Price
WestJet

AED 1,495

AED 1,455

FLYAE coupon applied

Winnipeg to Chicago , 28 Apr

WestJet WS | 205

21:05

Mon, 28 Apr 25

Winnipeg, Canada

02 h 12 m

22:17

Mon, 28 Apr 25

Calgary, Canada

BAGGAGE : CHECK INCABIN

Information not available

WestJet WS | 1992

00:30

Tue, 29 Apr 25

Calgary, Canada

04 h 24 m

06:54

Tue, 29 Apr 25

Terminal I

Atlanta, United States

BAGGAGE : CHECK INCABIN

Information not available

WestJet WS | 6651 | Operated By Delta Air Lines

17:50

Tue, 29 Apr 25

Terminal S

Atlanta, United States

02 h 10 m

19:00

Tue, 29 Apr 25

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate Change

Econo

Fare offered by airline.

1 Piece
Hand baggage only
Non-refundable fare
Date Change Fee starting
AED 696

AED 1,495AED 1,455

United Airlines

AED 1,644

AED 1,604

FLYAE coupon applied

Winnipeg to Chicago , 28 Apr

United Airlines UA | 5639

14:20

Mon, 28 Apr 25

Winnipeg, Canada

02 h 28 m

16:48

Mon, 28 Apr 25

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeat

MMT Value 1

Fare offered by airline.

1 Piece
Hand baggage only
Non-refundable fare
Date Change Fee starting
AED 696
----

AED 1,644AED 1,604

Economy

Fare offered by airline.

7 kg
Hand baggage only
Non-refundable fare
Free date change allowed
Free seats available

AED 1,653AED 1,613

Economy fully refundable

Fare offered by airline.

7 kg
Hand baggage only
No airline cancellation fee
Free date change allowed
Free seats available

AED 1,876AED 1,836

Economy plus

Fare offered by airline.

7 kg
Hand baggage only
Non-refundable fare
Free date change allowed
Free seats available

AED 1,910AED 1,870

Delta Air Lines

AED 1,649

AED 1,609

FLYAE coupon applied

Winnipeg to Chicago , 28 Apr

Delta Air Lines DL | 6936 | Operated By WestJet

08:30

Mon, 28 Apr 25

Winnipeg, Canada

02 h 11 m

09:41

Mon, 28 Apr 25

Calgary, Canada

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL | 7137 | Operated By WestJet

12:15

Mon, 28 Apr 25

Calgary, Canada

03 h 29 m

16:44

Mon, 28 Apr 25

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeatMeal

Main Cabin

Fare offered by airline.

1 Piece
Hand baggage only
Non-refundable fare
Date Change Fee starting
AED 699
----
----

AED 1,649AED 1,609

Main cabin

Fare offered by airline.

7 kg
Hand baggage only
Non-refundable fare
Free date change allowed
Free seats available
Complimentary meals (No meal will be served if flight duration is less than 2 hours)

AED 1,670AED 1,630

Refundable main cabin

Fare offered by airline.

7 kg
Hand baggage only
No airline cancellation fee
Free date change allowed
Free seats available
Complimentary meals (No meal will be served if flight duration is less than 2 hours)

AED 1,950AED 1,910

Air Canada

AED 1,651

AED 1,611

FLYAE coupon applied

Winnipeg to Chicago , 28 Apr

Air Canada AC | 3920 | Operated By United Airlines

14:20

Mon, 28 Apr 25

Winnipeg, Canada

02 h 28 m

16:48

Mon, 28 Apr 25

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeatMeal

Standard

Fare offered by airline.

1 Piece
Hand baggage only
Non-refundable fare
Date Change Fee starting
AED 630
----
----

AED 1,651AED 1,611

Standard

Fare offered by airline.

7 kg
Hand baggage only
Non-refundable fare
Date Change Fee starting
AED 265
----
Chargeable

AED 1,653AED 1,613

Flex

Fare offered by airline.

7 kg
23 kg (1 Pc.)
Non-refundable fare
Free date change allowed
----
Chargeable

AED 1,876AED 1,836

Latitude

Fare offered by airline.

7 kg
46 kg (2 Pc.)
No airline cancellation fee
Free date change allowed
Free seats available
No Meals

AED 3,510AED 3,470

Air Canada

More Timing Options

AED 1,659

AED 1,619

FLYAE coupon applied

Winnipeg to Chicago , 28 Apr

Air Canada AC | 260

07:30

Mon, 28 Apr 25

Winnipeg, Canada

02 h 31 m

11:01

Mon, 28 Apr 25

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC | 503

12:20

Mon, 28 Apr 25

Terminal T1

Toronto, Canada

01 h 55 m

13:15

Mon, 28 Apr 25

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeatMeal

Fare Option 1

Fare offered by airline.

Not allowed
Hand baggage only
Non-refundable fare
Date Change Fee starting
AED 545
Chargeable
No Meals

AED 1,659AED 1,619

Standard

Fare offered by airline.

0 kg
Hand baggage only
Non-refundable fare
Date Change Fee starting
AED 265
----
Chargeable

AED 1,696AED 1,656

Flex

Fare offered by airline.

0 kg
23 kg (1 Pc.)
Non-refundable fare
Free date change allowed
----
Chargeable

AED 1,920AED 1,880

Comfort

Fare offered by airline.

0 kg
46 kg (2 Pc.)
No airline cancellation fee
Free date change allowed
----
Chargeable

AED 2,170AED 2,130

Latitude

Fare offered by airline.

0 kg
46 kg (2 Pc.)
No airline cancellation fee
Free date change allowed
----
Complimentary meals (No meal will be served if flight duration is less than 2 hours)

AED 3,668AED 3,628

Winnipeg to Chicago Flights Information:-

Looking for Winnipeg to Chicago Flight? Here’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 4 airlines operating flights between the two destinations and approximately 69 flights take off from Winnipeg to Chicago every week. You can easily check the Winnipeg to Chicago Flight Schedule on Makemytrip.

Need information on Winnipeg to Chicago airfare?

The minimum airfare for a Winnipeg to Chicago flight would be 1455, which may go up to 3835 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, Delta Air Lines, United Airlines, WestJet. Out of these, only 2 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, Delta Air Lines : 19, United Airlines : 19, WestJet : 19

To board the first Winnipeg to Chicago flight, choose WestJet, which departs at 06:30 The last flight for this route is WestJet, departing at 21:05

Chicago Airport Information

Chicago Midway Intl

Frequently Asked Questions - Winnipeg to Chicago Flights

Q: Can I carry food on my Winnipeg to Chicago flight?

A: Airlines have varying rules on allowing passengers to carry their own food on the flight. Please check with the specific airline for further clarity on the same. Book Winnipeg to Chicago Flight now.

Q: What are the latest flight offers at MakeMyTrip for Winnipeg to Chicago?

A: MakeMyTrip offers cashback and instant discounts for Winnipeg to Chicago flights. Check the flights booking page for the exciting deals or you can check UAE Flight Offers here.

Q: Which is the cheapest airline on Winnipeg to Chicago flight route?

A: WestJet offers the cheapest flights from Winnipeg to Chicago. Book Winnipeg to Chicago Flight at discounted price.

Q: Which is the last flight on Winnipeg to Chicago route?

A: The last flight from Winnipeg to Chicago route is WestJet at 21:05. Book Winnipeg to Chicago Flight.

Q: What are the most booked classes for a Winnipeg to Chicago flight?

A: For Winnipeg to Chicago flights, most travellers prefer economy or business class tickets.

Q: Can I cancel my flight for free?

A: Yes, we provide zero cancellation fee, which will help you get a 100% refund on your flight cancellation, subject to some terms and conditions. So #BreakTheBookingRoutine now and book with no worries.

Q: Do I have to present an ID proof during check-in?

A: Yes, you need to present your passport during check-in for your international flight.

Q: Which are the most preferred airlines from Winnipeg to Chicago ?

A: Air Canada, Delta Air Lines, United Airlines, WestJet are the most preferred airlines on Winnipeg to Chicago flight route. Book Winnipeg to Chicago Flight at best price.

Q: Which are the most preferred airlines in the world?

A: The most preferred airlines in the world are Qatar Airways, Emirates, Lufthansa, Singapore Airlines, Oman Air and AirAsia. Lowest airfare for Winnipeg to Chicago Flight.

Q: Do airlines from Winnipeg to Chicago offer sleeping areas?

A: Several airlines flying from Winnipeg to Chicago provide space for sleeping. In most cases, this service is available on a pay per use basis. Book Winnipeg to Chicago Flight at MakeMyTrip.

Q: How many flights fly from Winnipeg to Chicago on the daily basis?

A: Around 69 flights are flying daily from Winnipeg to Chicago. Out of which 2 are direct flights on this route. Some major airlines between this route are Air Canada, Delta Air Lines, United Airlines, WestJet. Book Winnipeg to Chicago Flight at best price.

Q: What is today's cheapest fare from Winnipeg to Chicago?

A: Today lowest airfare on Winnipeg to Chicago flight route is AED1455 offered by WestJet at 21:05. Book Cheap Flight from Winnipeg to Chicago.

Q: What are the name and codes for Winnipeg and Chicago airports?

A: The name of Winnipeg airport is Winnipeg Intl and its code is YWG and name of Chicago Airport is Chicago Midway Intl, its code is CHI. Buy Winnipeg to Chicago Flight Ticket at cheapest rate.

Q: When does the first flight leave from Winnipeg to Chicago?

A: The first flight from Winnipeg to Chicago is WestJet at 06:30. Book Winnipeg to Chicago Flight at lowest airfare.

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

Hide

More Deals For You!

More discounts for your flight

Get Flat

12% OFF

MMTWELCOME

Grab Up to AED 60 OFF
*Applicable for First times user only.


Get Up To

20% OFF

FLYSUPER

Grab Up to AED 120 OFF
*T&C Applied


Get Up To

AED 150 OFF*

FLYAE

BIG Offer on Flights!
*T&C Applied


Show