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Cheap flights from Winnipeg to Chicago from C$ 239

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 5/6. 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
9:05 p.m. - 4:40 p.m.
YWG
-
ORD
19h 35m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 457WestJet
Thu, 10 Sep - Sun, 13 Sep
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$ 466WestJet
Thu, 20 Aug - Sun, 23 Aug
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$ 492WestJet
Sat, 23 May - Mon, 25 May
Multiple Airlines Logo
8:10 p.m. - 9:35 a.m.
YWG
-
MDW
13h 25m
1 stop
Multiple Airlines Logo
3:20 p.m. - 12:55 a.m.
MDW
-
YWG
9h 35m
1 stop
C$ 547Multiple Airlines
Fri, 5 Jun - Fri, 12 Jun
WestJet Logo
10:30 p.m. - 4:40 p.m.
YWG
-
ORD
18h 10m
2 stops
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 555WestJet
Thu, 10 Sep - Sun, 13 Sep
Multiple Airlines Logo
9:05 p.m. - 11:12 a.m.
YWG
-
MDW
14h 07m
2 stops
Multiple Airlines Logo
10:15 a.m. - 9:45 a.m.
MDW
-
YWG
23h 30m
1 stop
C$ 561Multiple Airlines
Mon, 8 Jun - Tue, 16 Jun
Multiple Airlines Logo
6:05 p.m. - 9:35 a.m.
YWG
-
MDW
15h 30m
1 stop
Multiple Airlines Logo
10:15 a.m. - 9:45 a.m.
MDW
-
YWG
23h 30m
1 stop
C$ 563Multiple Airlines
Mon, 8 Jun - Wed, 17 Jun
Multiple Airlines Logo
8:10 p.m. - 9:35 a.m.
YWG
-
MDW
13h 25m
1 stop
Multiple Airlines Logo
3:20 p.m. - 12:55 a.m.
MDW
-
YWG
9h 35m
1 stop
C$ 565Multiple Airlines
Fri, 5 Jun - Fri, 12 Jun
Porter Airlines Logo
8:45 p.m. - 9:35 a.m.
YWG
-
MDW
12h 50m
1 stop
Porter Airlines Logo
10:15 a.m. - 5:58 p.m.
MDW
-
YWG
7h 43m
2 stops
C$ 619Porter Airlines
Fri, 5 Jun - Fri, 12 Jun
Porter Airlines Logo
8:45 p.m. - 9:35 a.m.
YWG
-
MDW
12h 50m
1 stop
Porter Airlines Logo
10:15 a.m. - 5:58 p.m.
MDW
-
YWG
7h 43m
2 stops
C$ 630Porter Airlines
Fri, 5 Jun - Fri, 12 Jun

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
10 Sep
YWG9:05 p.m.Winnipeg
19h 35m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
13 Sep
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 457
WestJet
20 Aug
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
23 Aug
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 466
WestJet
23 May
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
25 May
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 492

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets
Porter Airlines
5 Jun
YWG8:45 p.m.Winnipeg
12h 50m
1 stop
MDW9:35 a.m.Chicago Midway
12 Jun
MDW10:15 a.m.Chicago Midway
7h 43m
2 stops
YWG5:58 p.m.Winnipeg
C$ 619
Porter Airlines
5 Jun
YWG8:45 p.m.Winnipeg
12h 50m
1 stop
MDW9:35 a.m.Chicago Midway
12 Jun
MDW10:15 a.m.Chicago Midway
7h 43m
2 stops
YWG5:58 p.m.Winnipeg
C$ 630
Porter Airlines
17 Oct
YWG9:20 a.m.Winnipeg
6h 35m
1 stop
ORD3:55 p.m.Chicago O'Hare Intl
21 Oct
ORD7:00 a.m.Chicago O'Hare Intl
10h 58m
2 stops
YWG5:58 p.m.Winnipeg
C$ 666

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 11 May 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

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/9

9:05 p.m.-4:40 p.m.

1 stop19h 35m

Chicago O'Hare Intl

Sun 13/9

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

1 stop7h 25m

C$ 457
Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 20/8

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

1 stop9h 40m

Chicago O'Hare Intl

Sun 23/8

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

1 stop7h 25m

C$ 466

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 23/5

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 25/5

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

1 stop7h 25m

C$ 492

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 5/6

8:10 p.m.-9:35 a.m.

1 stop13h 25m

Chicago Midway

Fri 12/6

3:20 p.m.-12:55 a.m.

1 stop9h 35m

C$ 547

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/9

10:30 p.m.-4:40 p.m.

2 stops18h 10m

Chicago O'Hare Intl

Sun 13/9

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

1 stop7h 25m

C$ 555

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 8/6

9:05 p.m.-11:12 a.m.

2 stops14h 07m

Chicago Midway

Tue 16/6

10:15 a.m.-9:45 a.m.

1 stop23h 30m

C$ 561

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 8/6

6:05 p.m.-9:35 a.m.

1 stop15h 30m

Chicago Midway

Wed 17/6

10:15 a.m.-9:45 a.m.

1 stop23h 30m

C$ 563

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 5/6

8:10 p.m.-9:35 a.m.

1 stop13h 25m

Chicago Midway

Fri 12/6

3:20 p.m.-12:55 a.m.

1 stop9h 35m

C$ 565

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 5/6

8:45 p.m.-9:35 a.m.

1 stop12h 50m

Chicago Midway

Fri 12/6

10:15 a.m.-5:58 p.m.

2 stops7h 43m

C$ 619

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 5/6

8:45 p.m.-9:35 a.m.

1 stop12h 50m

Chicago Midway

Fri 12/6

10:15 a.m.-5:58 p.m.

2 stops7h 43m

C$ 630

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 typical price of a round-trip flight between Winnipeg and Chicago?

What is the cheapest month to fly to Chicago?

The month of May is another great option to travel to Chicago, with average flight prices from Winnipeg averaging around C$ 123.

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$ 780. 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 Monday because tickets tend to average around C$ 1,082. 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$ 835. 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$ 950 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

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 May 2026, prices for Winnipeg to Chicago flights are approximately 17% 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$ 331

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is C$ 331. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 598.
The fastest flight from Winnipeg to Chicago takes 2h 21m
Direct flights go from Winnipeg to Chicago every day.
There are 3 airports in Chicago. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Winnipeg to Chicago

  • 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$ 268Free CancellationRating
7.2
3,332 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 361Free CancellationRating
7.1
11,017 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 481Free CancellationRating
7.4
9,699 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$ 768, 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 9,699 reviews.

  • Air Canada Flights From Winnipeg to Chicago

    Air Canada (7.1/10 from 11,017 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 759, with deals from around C$ 361 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
Merrillville
Hammond
Munster

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