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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 15/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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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
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$ 294WestJet
Thu, 21 May - Sun, 24 May
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$ 371WestJet
Mon, 20 Apr - Fri, 24 Apr
WestJet Logo
10:55 a.m. - 1:35 p.m.
YWG
-
ORD
26h 40m
1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
C$ 413WestJet
Sun, 19 Apr - Fri, 24 Apr
Multiple Airlines Logo
7:30 a.m. - 8:07 p.m.
YWG
-
MDW
12h 37m
1 stop
Multiple Airlines Logo
6:10 a.m. - 12:40 a.m.
MDW
-
YWG
18h 30m
2 stops
C$ 421Multiple Airlines
Wed, 8 Apr - Wed, 15 Apr
Multiple Airlines Logo
7:30 a.m. - 8:07 p.m.
YWG
-
MDW
12h 37m
1 stop
Multiple Airlines Logo
6:10 a.m. - 3:09 p.m.
MDW
-
YWG
8h 59m
1 stop
C$ 424Multiple Airlines
Wed, 8 Apr - Wed, 15 Apr
Multiple Airlines Logo
7:30 a.m. - 10:39 p.m.
YWG
-
ORD
15h 09m
1 stop
Multiple Airlines Logo
11:07 a.m. - 12:40 a.m.
ORD
-
YWG
13h 33m
2 stops
C$ 430Multiple Airlines
Wed, 8 Apr - Wed, 15 Apr
Multiple Airlines Logo
9:05 p.m. - 2:20 p.m.
YWG
-
ORD
17h 15m
2 stops
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 431Multiple Airlines
Thu, 21 May - Sun, 24 May
Multiple Airlines Logo
7:30 a.m. - 8:07 p.m.
YWG
-
MDW
12h 37m
1 stop
Multiple Airlines Logo
6:10 a.m. - 12:40 a.m.
MDW
-
YWG
18h 30m
2 stops
C$ 436Multiple Airlines
Wed, 8 Apr - Wed, 15 Apr
Multiple Airlines Logo
7:30 a.m. - 8:07 p.m.
YWG
-
MDW
12h 37m
1 stop
Multiple Airlines Logo
6:10 a.m. - 3:09 p.m.
MDW
-
YWG
8h 59m
1 stop
C$ 440Multiple Airlines
Wed, 8 Apr - Wed, 15 Apr
Multiple Airlines Logo
7:30 a.m. - 10:39 p.m.
YWG
-
ORD
15h 09m
1 stop
Multiple Airlines Logo
11:07 a.m. - 12:40 a.m.
ORD
-
YWG
13h 33m
2 stops
C$ 445Multiple Airlines
Wed, 8 Apr - Wed, 15 Apr

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
21 May
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
24 May
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 294
WestJet
20 Apr
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
24 Apr
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
C$ 371
WestJet
19 Apr
YWG10:55 a.m.Winnipeg
26h 40m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
24 Apr
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
C$ 413

United Airlines flights from Winnipeg to Chicago

Our best United Airlines deals on Winnipeg to Chicago flight tickets
United Airlines
2 Mar
YWG2:20 p.m.Winnipeg
2h 25m
ORD4:45 p.m.Chicago O'Hare Intl
4 Mar
ORD9:15 a.m.Chicago O'Hare Intl
2h 42m
YWG11:57 a.m.Winnipeg
C$ 1,074
United Airlines
2 Mar
YWG2:20 p.m.Winnipeg
2h 25m
ORD4:45 p.m.Chicago O'Hare Intl
4 Mar
ORD9:15 a.m.Chicago O'Hare Intl
2h 42m
YWG11:57 a.m.Winnipeg
C$ 1,124
United Airlines
2 Mar
YWG2:20 p.m.Winnipeg
2h 25m
ORD4:45 p.m.Chicago O'Hare Intl
4 Mar
ORD9:15 a.m.Chicago O'Hare Intl
2h 42m
YWG11:57 a.m.Winnipeg
C$ 1,126

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 22 February 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

Thu 21/5

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

1 stop9h 40m

Chicago O'Hare Intl

Sun 24/5

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

1 stop7h 25m

C$ 294

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 20/4

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

1 stop7h 20m

Chicago O'Hare Intl

Fri 24/4

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

1 stop8h 20m

C$ 371

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 19/4

10:55 a.m.-1:35 p.m.

1 stop26h 40m

Chicago O'Hare Intl

Fri 24/4

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

1 stop8h 20m

C$ 413

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/4

7:30 a.m.-8:07 p.m.

1 stop12h 37m

Chicago Midway

Wed 15/4

6:10 a.m.-12:40 a.m.

2 stops18h 30m

C$ 421

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/4

7:30 a.m.-8:07 p.m.

1 stop12h 37m

Chicago Midway

Wed 15/4

6:10 a.m.-3:09 p.m.

1 stop8h 59m

C$ 424

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 8/4

7:30 a.m.-10:39 p.m.

1 stop15h 09m

Chicago O'Hare Intl

Wed 15/4

11:07 a.m.-12:40 a.m.

2 stops13h 33m

C$ 430

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 21/5

9:05 p.m.-2:20 p.m.

2 stops17h 15m

Chicago O'Hare Intl

Sun 24/5

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

1 stop7h 25m

C$ 431

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/4

7:30 a.m.-8:07 p.m.

1 stop12h 37m

Chicago Midway

Wed 15/4

6:10 a.m.-12:40 a.m.

2 stops18h 30m

C$ 436

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/4

7:30 a.m.-8:07 p.m.

1 stop12h 37m

Chicago Midway

Wed 15/4

6:10 a.m.-3:09 p.m.

1 stop8h 59m

C$ 440

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 8/4

7:30 a.m.-10:39 p.m.

1 stop15h 09m

Chicago O'Hare Intl

Wed 15/4

11:07 a.m.-12:40 a.m.

2 stops13h 33m

C$ 445

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$ 490.

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$ 763. 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$ 1,020. 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$ 924 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 42% 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 February 2026, prices for Winnipeg to Chicago flights are approximately 11% cheaper 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$ 315

Fastest flight time

2h 21m

Direct flights

Mon, Tue, 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$ 315. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 522.
The fastest flight from Winnipeg to Chicago takes 2h 21m
Direct flights go from Winnipeg to Chicago on Monday, Tuesday, 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$ 198Free CancellationRating
7.2
3,270 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 357Free CancellationRating
7.1
10,738 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 481Free CancellationRating
7.4
9,341 reviews
Search United Airlines flights

  • United Airlines Flights From Winnipeg to Chicago

    United Airlines operates around 6 flights from Winnipeg to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 644, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 481 round-trip. United Airlines has been scored 7.4/10 in 9,341 reviews.

  • Air Canada Flights From Winnipeg to Chicago

    Air Canada (7.1/10 from 10,738 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 696, with deals from around C$ 357 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