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Cheap flights from Winnipeg to Chicago from C$ 201

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Chicago departing on 29/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:55 p.m. - 4:40 p.m.
YWG
-
ORD
21h 45m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 349WestJet
Sat, 25 Apr - Thu, 30 Apr
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
2 stops
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 353WestJet
Fri, 5 Jun - Tue, 9 Jun
WestJet Logo
9:00 p.m. - 4:40 p.m.
YWG
-
ORD
19h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 354WestJet
Sat, 25 Apr - Thu, 30 Apr
WestJet Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m
1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
C$ 356WestJet
Fri, 6 Mar - Mon, 9 Mar
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 360WestJet
Fri, 5 Jun - Tue, 9 Jun
WestJet Logo
12:55 p.m. - 4:40 p.m.
YWG
-
ORD
27h 45m
2 stops
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 391WestJet
Sat, 25 Apr - Thu, 30 Apr
Multiple Airlines Logo
7:30 a.m. - 11:16 a.m.
YWG
-
ORD
27h 46m
1 stop
Multiple Airlines Logo
7:41 p.m. - 12:40 a.m.
ORD
-
YWG
28h 59m
2 stops
C$ 392Multiple Airlines
Fri, 6 Mar - Tue, 10 Mar
Multiple Airlines Logo
7:30 a.m. - 11:16 a.m.
YWG
-
ORD
27h 46m
1 stop
Multiple Airlines Logo
7:41 p.m. - 3:09 p.m.
ORD
-
YWG
19h 28m
1 stop
C$ 395Multiple Airlines
Fri, 6 Mar - Tue, 10 Mar
WestJet Logo
5:00 p.m. - 4:40 p.m.
YWG
-
ORD
23h 40m
2 stops
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 396WestJet
Sat, 25 Apr - Thu, 30 Apr
WestJet Logo
9:00 p.m. - 1:35 p.m.
YWG
-
ORD
16h 35m
1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
C$ 399WestJet
Thu, 5 Mar - Mon, 9 Mar

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
25 Apr
YWG6:55 p.m.Winnipeg
21h 45m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 349
WestJet
5 Jun
YWG7:00 a.m.Winnipeg
9h 40m
2 stops
ORD4:40 p.m.Chicago O'Hare Intl
9 Jun
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 353
WestJet
25 Apr
YWG9:00 p.m.Winnipeg
19h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 354

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets
Porter Airlines
3 Mar
YWG12:10 p.m.Winnipeg
7h 07m
1 stop
ORD7:17 p.m.Chicago O'Hare Intl
8 Mar
ORD1:22 p.m.Chicago O'Hare Intl
10h 13m
1 stop
YWG11:35 p.m.Winnipeg
C$ 677
Porter Airlines
3 Mar
YWG12:10 p.m.Winnipeg
7h 07m
1 stop
ORD7:17 p.m.Chicago O'Hare Intl
8 Mar
ORD1:22 p.m.Chicago O'Hare Intl
10h 13m
1 stop
YWG11:35 p.m.Winnipeg
C$ 679
Porter Airlines
6 Mar
YWG4:25 p.m.Winnipeg
19h 25m
2 stops
MDW11:50 a.m.Chicago Midway
9 Mar
MDW11:00 a.m.Chicago Midway
24h 13m
2 stops
YWG11:13 a.m.Winnipeg
C$ 889

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 29 January 2026.
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

6:55 p.m.-4:40 p.m.

1 stop21h 45m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 349

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/6

7:00 a.m.-4:40 p.m.

2 stops9h 40m

Chicago O'Hare Intl

Tue 9/6

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 353

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

9:00 p.m.-4:40 p.m.

1 stop19h 40m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 354

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 6/3

6:15 a.m.-1:35 p.m.

1 stop7h 20m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 356

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/6

7:00 a.m.-4:40 p.m.

1 stop9h 40m

Chicago O'Hare Intl

Tue 9/6

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 360

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

12:55 p.m.-4:40 p.m.

2 stops27h 45m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 391

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 6/3

7:30 a.m.-11:16 a.m.

1 stop27h 46m

Chicago O'Hare Intl

Tue 10/3

7:41 p.m.-12:40 a.m.

2 stops28h 59m

C$ 392

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 6/3

7:30 a.m.-11:16 a.m.

1 stop27h 46m

Chicago O'Hare Intl

Tue 10/3

7:41 p.m.-3:09 p.m.

1 stop19h 28m

C$ 395

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

5:00 p.m.-4:40 p.m.

2 stops23h 40m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 396

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/3

9:00 p.m.-1:35 p.m.

1 stop16h 35m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 399

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Winnipeg to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of October is another great option to travel to Chicago, with average flight prices from Winnipeg averaging around C$ 486.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 771. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 1,010. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the morning is the cheapest time of day to fly from Winnipeg to Chicago when you can find flight prices for as low as C$ 833. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 912 per ticket.

What is the cheapest Winnipeg to Chicago flight route?

Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Chicago flight prices

What cabin class options are available on Winnipeg to Chicago flights?

There are 4 cabin classes available to choose from on Winnipeg to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Winnipeg to Chicago flights?

You could potentially save up to 64% on your flight if you consider stops on a Winnipeg to Chicago flight.

How have Winnipeg to Chicago flight prices changed over time?

As of January 2026, prices for Winnipeg to Chicago flights are approximately 52% more expensive when compared to flights at the same time last year.

When to book flights from Winnipeg to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Winnipeg to Chicago (YWG to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago

Best price found

C$ 257

Fastest flight time

2h 21m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is C$ 257. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 674.
The fastest flight from Winnipeg to Chicago takes 2h 21m
Direct flights go from Winnipeg to Chicago on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • How far is Winnipeg to Chicago by plane?

    A flight from Winnipeg to Chicago will travel around 1153.0 km. 2h 21m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Winnipeg Airport to Chicago?

    Prices for flights from Winnipeg Airport to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Winnipeg Airport to Chicago?

  • How old do you have to be to fly from Winnipeg Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Winnipeg Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Winnipeg to Chicago?

  • What is the most popular airline from Winnipeg to Chicago?

Best airlines flying from Winnipeg to Chicago

Compare and see reviews for airlines that fly from Winnipeg to Chicago with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 196Free CancellationRating
7.2
3,253 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 355Free CancellationRating
7.1
10,667 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 478Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights

  • United Airlines Flights From Winnipeg to Chicago

    United Airlines operates around 7 flights from Winnipeg to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 639, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 478 round-trip. United Airlines has been scored 7.4/10 in 9,215 reviews.

  • Air Canada Flights From Winnipeg to Chicago

    Air Canada (7.1/10 from 10,667 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 716, with deals from around C$ 355 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Chicago?

Finding the right flight to Chicago from Winnipeg is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Winnipeg which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Winnipeg to Chicago?

Once you have performed a search for Winnipeg to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Winnipeg. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport