What is the cheapest airline that flies from Winnipeg to Chicago?

Porter Airlines is the most popular carrier operating from Winnipeg to Chicago

How many flights depart from Winnipeg to Chicago on average per week?

As of October 2026, there are 52 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.

How many flights depart from Winnipeg to Chicago on average per day?

As of October 2026, 7 flights take off from Winnipeg and land in Chicago each day. The most common flight departure time for this route is 2:00p.m., with 53% of daily flights taking off in the afternoon.

Which airlines fly to Chicago?

United Airlines, Air Canada and WestJet are the top three most popular airlines that fly to Chicago from Winnipeg according to our data. United Airlines is the first choice among our users, with 35% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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?

As of October 2026, there are 3 operators available to choose from 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.

C$ 273 Cheap Flights from Winnipeg to Chicago in 2026/27

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Find the cheapest flights from Winnipeg to Chicago

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Cheap round-trip flights

Enter your travel dates to find the best prices.

9:35 p.m. - 2:30 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 55m2 stops Calgary Atlanta Hartsfield-Jackson

6:00 a.m. - 2:40 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 40m1 stop Atlanta Hartsfield-Jackson

C$ 522Multiple Airlines

Mon, 14 Dec - Wed, 6 Jan

7:00 a.m. - 11:23 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 23m1 stop Atlanta Hartsfield-Jackson

6:00 a.m. - 2:40 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 40m1 stop Atlanta Hartsfield-Jackson

C$ 544Multiple Airlines

Fri, 12 Feb - Wed, 17 Feb

7:00 a.m. - 9:42 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

14h 42m1 stop Atlanta Hartsfield-Jackson

6:00 a.m. - 2:40 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 40m1 stop Atlanta Hartsfield-Jackson

C$ 558Multiple Airlines

Mon, 14 Dec - Wed, 6 Jan

1:45 p.m. - 12:46 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

23h 01m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

2:25 p.m. - 2:47 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

24h 22m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl

C$ 960United Airlines

Wed, 24 Feb - Sun, 28 Feb

6:15 a.m. - 11:57 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

5h 42m1 stop Toronto Pearson Intl

12:55 p.m. - 12:44 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

11h 49m2 stops Newark Toronto Pearson Intl

C$ 1,012Air Canada

Fri, 4 Dec - Tue, 8 Dec

6:15 a.m. - 6:20 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

12h 05m2 stops Toronto Pearson Intl Ottawa

1:57 p.m. - 10:24 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 27m1 stop Toronto Pearson Intl

C$ 1,012Air Canada

Wed, 2 Dec - Tue, 8 Dec

1:45 p.m. - 11:25 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

21h 40m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

6:08 p.m. - 3:09 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

21h 01m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl

C$ 1,070United Airlines

Tue, 15 Dec - Wed, 16 Dec

12:45 p.m. - 9:04 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

20h 19m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

6:20 p.m. - 1:48 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

19h 28m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl

C$ 1,074United Airlines

Thu, 15 Apr - Mon, 19 Apr

9:35 p.m. - 12:24 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

14h 49m2 stops Calgary Atlanta Hartsfield-Jackson

3:47 p.m. - 12:39 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 52m1 stop Minneapolis St Paul

C$ 1,102WestJet

Mon, 30 Nov - Sat, 5 Dec

5:45 p.m. - 7:39 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

25h 54m1 stop Minneapolis St Paul

7:25 a.m. - 5:25 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

34h 00m2 stops Salt Lake City Calgary

C$ 1,110WestJet

Sun, 29 Nov - Thu, 3 Dec

Cheap last-minute flights

Enter your travel dates to find the best prices.

9:05 p.m. - 11:32 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

14h 27m2 stops Calgary Atlanta Hartsfield-Jackson

6:10 a.m. - 6:45 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

12h 35m1 stop Cancun

C$ 1,148Multiple Airlines

Fri, 23 Oct - Mon, 26 Oct

9:05 p.m. - 6:31 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

21h 26m2 stops Calgary Atlanta Hartsfield-Jackson

6:10 a.m. - 6:45 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

12h 35m1 stop Cancun

C$ 1,227Multiple Airlines

Sat, 24 Oct - Mon, 26 Oct

8:10 p.m. - 8:39 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

12h 29m1 stop Toronto Pearson Intl

8:00 a.m. - 9:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

25h 15m2 stops Fort Lauderdale Toronto Pearson Intl

C$ 1,279Multiple Airlines

Fri, 23 Oct - Fri, 30 Oct

9:05 p.m. - 12:13 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

15h 08m2 stops Calgary Atlanta Hartsfield-Jackson

11:21 a.m. - 1:10 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

13h 49m2 stops Atlanta Hartsfield-Jackson Calgary

C$ 1,405WestJet

Fri, 23 Oct - Mon, 26 Oct

5:40 p.m. - 11:47 a.m.YWG Winnipeg-MDW Chicago Midway

18h 07m1 stop Minneapolis St Paul

5:31 p.m. - 11:19 p.m.MDW Chicago Midway-YWG Winnipeg

5h 48m1 stop Minneapolis St Paul

C$ 1,405WestJet

Sat, 24 Oct - Mon, 26 Oct

6:00 a.m. - 6:00 p.m.YWG Winnipeg-MDW Chicago Midway

12h 00m2 stops Calgary Detroit Metropolitan Wayne County

10:12 a.m. - 4:50 p.m.MDW Chicago Midway-YWG Winnipeg

6h 38m1 stop Minneapolis St Paul

C$ 1,405WestJet

Sat, 24 Oct - Mon, 26 Oct

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

8:40 a.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

12h 17m1 stop Denver Intl

C$ 1,556United Airlines

Fri, 23 Oct - Fri, 30 Oct

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

8:40 a.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

12h 17m1 stop Denver Intl

C$ 1,638United Airlines

Tue, 20 Oct - Wed, 21 Oct

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

C$ 1,686Air Canada

Tue, 20 Oct - Wed, 21 Oct

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

10:55 a.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

10h 02m1 stop Denver Intl

C$ 1,727Air Canada

Wed, 21 Oct - Sat, 24 Oct

Cheap direct flights

Enter your travel dates to find the best prices.

8:00 a.m. - 9:31 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 31mdirect

3:50 p.m. - 7:41 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 51mdirect

C$ 1,081United Airlines

Thu, 25 Feb - Sun, 28 Feb

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

C$ 1,094United Airlines

Wed, 25 Nov - Sat, 28 Nov

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

C$ 1,098United Airlines

Sat, 21 Nov - Sun, 22 Nov

8:00 a.m. - 9:31 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 31mdirect

3:50 p.m. - 7:41 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 51mdirect

C$ 1,112United Airlines

Fri, 12 Feb - Wed, 17 Feb

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

C$ 1,132Lufthansa

Thu, 19 Nov - Sun, 22 Nov

3:15 p.m. - 5:00 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 45mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

C$ 1,217Air Canada

Tue, 1 Dec - Sat, 5 Dec

3:15 p.m. - 5:00 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 45mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

C$ 1,217Multiple Airlines

Fri, 4 Dec - Mon, 7 Dec

3:15 p.m. - 5:00 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 45mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

C$ 1,220Air Canada

Tue, 1 Dec - Sat, 5 Dec

3:15 p.m. - 5:02 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 47mdirect

10:00 a.m. - 1:52 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 52mdirect

C$ 1,225Multiple Airlines

Wed, 23 Dec - Wed, 30 Dec

3:15 p.m. - 5:02 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 47mdirect

10:00 a.m. - 1:52 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 52mdirect

C$ 1,225Air Canada

Wed, 23 Dec - Tue, 29 Dec

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American Airlines flights from Winnipeg to Chicago

Our best American Airlines deals on Winnipeg to Chicago flight tickets

American Airlines

1 Dec

YWG7:00 a.m.Winnipeg

6h 10m

1 stop

ORD1:10 p.m.Chicago O'Hare Intl

7 Dec

ORD2:50 p.m.Chicago O'Hare Intl

8h 07m

1 stop

YWG10:57 p.m.Winnipeg

C$ 769

American Airlines

1 Dec

YWG7:00 a.m.Winnipeg

6h 10m

1 stop

ORD1:10 p.m.Chicago O'Hare Intl

5 Dec

ORD2:50 p.m.Chicago O'Hare Intl

8h 07m

1 stop

YWG10:57 p.m.Winnipeg

C$ 770

American Airlines

12 Nov

YWG7:00 a.m.Winnipeg

7h 37m

1 stop

ORD2:37 p.m.Chicago O'Hare Intl

17 Nov

ORD2:50 p.m.Chicago O'Hare Intl

8h 02m

1 stop

YWG10:52 p.m.Winnipeg

C$ 773

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets

Porter Airlines

25 Nov

YWG7:00 a.m.Winnipeg

6h 10m

1 stop

ORD1:10 p.m.Chicago O'Hare Intl

28 Nov

ORD2:50 p.m.Chicago O'Hare Intl

8h 02m

1 stop

YWG10:52 p.m.Winnipeg

C$ 777

Porter Airlines

2 Dec

YWG7:00 a.m.Winnipeg

7h 42m

1 stop

ORD2:42 p.m.Chicago O'Hare Intl

5 Dec

ORD2:50 p.m.Chicago O'Hare Intl

8h 07m

1 stop

YWG10:57 p.m.Winnipeg

C$ 779

Porter Airlines

28 Nov

YWG7:00 a.m.Winnipeg

6h 10m

1 stop

ORD1:10 p.m.Chicago O'Hare Intl

5 Dec

ORD2:50 p.m.Chicago O'Hare Intl

8h 07m

1 stop

YWG10:57 p.m.Winnipeg

C$ 794

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 14/12

9:35 p.m.-2:30 p.m.

2 stops16h 55m

Chicago O'Hare Intl

Wed 6/1

6:00 a.m.-2:40 p.m.

1 stop8h 40m

C$ 522

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 12/2

7:00 a.m.-11:23 p.m.

1 stop16h 23m

Chicago O'Hare Intl

Wed 17/2

6:00 a.m.-2:40 p.m.

1 stop8h 40m

C$ 544

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 14/12

7:00 a.m.-9:42 p.m.

1 stop14h 42m

Chicago O'Hare Intl

Wed 6/1

6:00 a.m.-2:40 p.m.

1 stop8h 40m

C$ 558

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 24/2

1:45 p.m.-12:46 p.m.

2 stops23h 01m

Chicago O'Hare Intl

Sun 28/2

2:25 p.m.-2:47 p.m.

2 stops24h 22m

C$ 960

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 4/12

6:15 a.m.-11:57 a.m.

1 stop5h 42m

Chicago O'Hare Intl

Tue 8/12

12:55 p.m.-12:44 a.m.

2 stops11h 49m

C$ 1,012

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 2/12

6:15 a.m.-6:20 p.m.

2 stops12h 05m

Chicago O'Hare Intl

Tue 8/12

1:57 p.m.-10:24 p.m.

1 stop8h 27m

C$ 1,012

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 15/12

1:45 p.m.-11:25 a.m.

2 stops21h 40m

Chicago O'Hare Intl

Wed 16/12

6:08 p.m.-3:09 p.m.

2 stops21h 01m

C$ 1,070

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 15/4

12:45 p.m.-9:04 a.m.

2 stops20h 19m

Chicago O'Hare Intl

Mon 19/4

6:20 p.m.-1:48 p.m.

2 stops19h 28m

C$ 1,074

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 30/11

9:35 p.m.-12:24 p.m.

2 stops14h 49m

Chicago O'Hare Intl

Sat 5/12

3:47 p.m.-12:39 a.m.

1 stop8h 52m

C$ 1,102

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 29/11

5:45 p.m.-7:39 p.m.

1 stop25h 54m

Chicago O'Hare Intl

Thu 3/12

7:25 a.m.-5:25 p.m.

2 stops34h 00m

C$ 1,110

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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

Prices are currently low for flights on this route.

Typical prices usually range from C$ 670 to C$ 988.
The lowest price recently found on this route was C$ 522.

What is the cheapest month to fly to Chicago?

The month of January is another great option to travel to Chicago, with average flight prices from Winnipeg averaging around C$ 728.

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 Wednesday when prices can be found for as low as C$ 868. 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$ 1,197. 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 afternoon is the cheapest time of day to fly from Winnipeg to Chicago when you can find flight prices for as low as C$ 869. Flying to Chicago in the afternoon 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$ 1,040 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 31% 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 October 2026, prices for Winnipeg to Chicago flights are approximately 23% 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$ 273
Fastest flight time	1h 31m
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$ 273. 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 1h 31m

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. 1h 31m 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?
As of October 2026, there are 3 operators available to choose from 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Winnipeg to Chicago is Embraer 175 (Enhanced Winglets) (88.19% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (5.51%), Boeing 737-700 Passenger/BBJ1 (winglets) (1.57%), and Boeing 737-800 Passenger/BBJ2 (winglets) (1.57%).
What is the most popular airline from Winnipeg to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Winnipeg to Chicago is Air Canada (46% of total bookings). The next most popular airlines are United Airlines (27%) and WestJet (26%).

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
WestJet	PriceFrom C$ 277	Free Cancellation	Rating 7.2 3,447 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 701	Free Cancellation	Rating 7.3 10,389 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 720	Free Cancellation	Rating 7.1 11,782 reviews	Search Air Canada flights

United Airlines Flights From Winnipeg to Chicago
United Airlines operates around 12 flights from Winnipeg to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 978, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 701 round-trip. United Airlines has been scored 7.3/10 in 10,388 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 11,782 reviews) operates around 14 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 889, with deals from around C$ 720 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.

Merrillville

Benton Harbor

Hammond

Munster

Valparaiso

Portage

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.

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Fly into one of these airports located in Chicago

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Cheap flights from Winnipeg to Chicago from C$ 273

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 15/1. 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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Cheap last-minute flights

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American Airlines flights from Winnipeg to Chicago

Our best American Airlines deals on Winnipeg to Chicago flight tickets

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets

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Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Winnipeg to Chicago

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

What is the cheapest month to fly to Chicago?

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

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

What is the cheapest Winnipeg to Chicago flight route?

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

Can stopping save me money on Winnipeg to Chicago flights?

How have Winnipeg to Chicago flight prices changed over time?

What is the cheapest airline that flies from Winnipeg to Chicago?

Which airlines fly to Chicago?

How many flights depart from Winnipeg to Chicago on average per day?

How many flights depart from Winnipeg to Chicago on average per week?

When to book flights from Winnipeg to Chicago

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

Best price found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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

Travelling to a place near Chicago?

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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

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular Cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Winnipeg

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year