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

As of October 2026, there are 6 flights per day flying from Chicago to Winnipeg. The most common time of day flights depart is 7:00p.m., with 53% of flights taking off in the evening.

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

As of October 2026, 47 flights take off from Chicago and land in Winnipeg each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.

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

Prices for flights from Chicago to Winnipeg Airport are updated daily.

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

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 Chicago to Winnipeg Airport.

What documentation or ID do you need to fly to Winnipeg Airport?

The necessary travel and health documents for your Winnipeg Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

C$ 276 Cheap Flights from Chicago to Winnipeg in 2026/27

Find the cheapest flights from Chicago to Winnipeg

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 a.m. - 3:40 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 40m1 stop Atlanta Hartsfield-Jackson

9:35 p.m. - 10:23 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

25h 48m2 stops Calgary Atlanta Hartsfield-Jackson

C$ 645Multiple Airlines

Fri, 15 Jan - Sun, 17 Jan

7:49 a.m. - 2:10 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

17h 21m2 stops Atlanta Hartsfield-Jackson Calgary

7:55 p.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

21h 45m1 stop Toronto Pearson Intl

C$ 670Multiple Airlines

Thu, 26 Nov - Sun, 29 Nov

6:20 p.m. - 11:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 55m1 stop Toronto Island

7:55 p.m. - 10:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

15h 40m1 stop Toronto Pearson Intl

C$ 683Multiple Airlines

Thu, 26 Nov - Sun, 29 Nov

7:35 p.m. - 11:55 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

27h 20m2 stops Atlanta Hartsfield-Jackson Calgary

9:35 p.m. - 5:30 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

20h 55m2 stops Calgary Atlanta Hartsfield-Jackson

C$ 693Multiple Airlines

Tue, 10 Nov - Tue, 17 Nov

7:35 p.m. - 2:10 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

29h 35m2 stops Atlanta Hartsfield-Jackson Calgary

9:35 p.m. - 4:07 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

19h 32m3 stops Calgary Atlanta Hartsfield-Jackson Orlando

C$ 768Multiple Airlines

Tue, 10 Nov - Tue, 17 Nov

6:00 a.m. - 3:40 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 40m1 stop Atlanta Hartsfield-Jackson

9:05 p.m. - 10:40 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

14h 35m1 stop Toronto Pearson Intl

C$ 784Multiple Airlines

Fri, 15 Jan - Sun, 17 Jan

5:26 p.m. - 9:45 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

27h 19m2 stops Atlanta Hartsfield-Jackson Calgary

9:35 p.m. - 12:44 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 09m2 stops Calgary Atlanta Hartsfield-Jackson

C$ 791Multiple Airlines

Sat, 21 Nov - Wed, 25 Nov

8:40 p.m. - 1:05 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 25m1 stop Toronto Pearson Intl

6:00 a.m. - 6:58 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

13h 58m1 stop Toronto Pearson Intl

C$ 804Multiple Airlines

Sat, 28 Nov - Sat, 5 Dec

7:50 p.m. - 2:10 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

29h 20m2 stops Atlanta Hartsfield-Jackson Calgary

10:00 a.m. - 5:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

8h 35m2 stops Regina Minneapolis St Paul

C$ 807Multiple Airlines

Thu, 5 Nov - Thu, 12 Nov

8:40 p.m. - 1:05 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 25m1 stop Toronto Pearson Intl

6:00 a.m. - 6:52 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

13h 52m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

C$ 812Multiple Airlines

Sat, 28 Nov - Sat, 5 Dec

Cheap last-minute flights

Enter your travel dates to find the best prices.

11:45 a.m. - 7:50 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 05m1 stop Toronto Pearson Intl

9:20 a.m. - 4:14 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

6h 54m1 stop Toronto Pearson Intl

C$ 1,658Porter Airlines

Tue, 20 Oct - Sat, 24 Oct

11:45 a.m. - 7:50 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 05m1 stop Toronto Pearson Intl

4:15 p.m. - 8:39 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 24m2 stops Ottawa Toronto Pearson Intl

C$ 1,793Porter Airlines

Tue, 20 Oct - Sat, 24 Oct

11:45 a.m. - 7:50 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 05m1 stop Toronto Pearson Intl

4:15 p.m. - 8:39 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 24m2 stops Ottawa Toronto Pearson Intl

C$ 1,796Porter Airlines

Tue, 20 Oct - Sat, 24 Oct

11:45 a.m. - 7:50 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 05m1 stop Toronto Pearson Intl

9:20 a.m. - 8:39 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

23h 19m1 stop Toronto Pearson Intl

C$ 1,796Porter Airlines

Tue, 20 Oct - Sat, 24 Oct

8:06 a.m. - 3:20 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 14m1 stop Toronto Pearson Intl

6:55 p.m. - 8:39 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

13h 44m1 stop Toronto Pearson Intl

C$ 1,814Porter Airlines

Sat, 17 Oct - Sun, 18 Oct

10:00 a.m. - 12:37 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

7:20 a.m. - 5:05 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 45m1 stop Calgary

C$ 1,840Air Canada

Tue, 20 Oct - Sat, 24 Oct

12:30 p.m. - 4:50 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

4h 20m1 stop Minneapolis St Paul

10:30 p.m. - 5:16 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

30h 46m2 stops Edmonton Las Vegas Harry Reid Intl

C$ 1,898Multiple Airlines

Sat, 17 Oct - Sun, 18 Oct

11:45 a.m. - 10:43 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

22h 58m2 stops Toronto Pearson Intl Ottawa

4:15 p.m. - 8:39 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 24m2 stops Ottawa Toronto Pearson Intl

C$ 1,918Porter Airlines

Tue, 20 Oct - Sat, 24 Oct

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

2h 39mdirect

5:00 a.m. - 12:00 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

7h 00m1 stop Toronto Pearson Intl

C$ 1,920Air Canada

Tue, 20 Oct - Sat, 24 Oct

10:00 a.m. - 12:37 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

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

2h 35mdirect

C$ 1,964United Airlines

Tue, 20 Oct - Sat, 24 Oct

Cheap direct flights

Enter your travel dates to find the best prices.

9:35 a.m. - 2:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

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

1h 35mdirect

C$ 1,350Air Canada

Thu, 26 Nov - Sun, 29 Nov

9:35 a.m. - 2:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

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

1h 35mdirect

C$ 1,350Air Canada

Tue, 10 Nov - Tue, 17 Nov

9:15 a.m. - 11:39 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 24mdirect

2:15 p.m. - 4:36 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 21mdirect

C$ 1,360Air Canada

Tue, 13 Apr - Mon, 19 Apr

9:29 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 54mdirect

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

1h 35mdirect

C$ 1,386Air Canada

Wed, 28 Oct - Mon, 2 Nov

9:35 a.m. - 2:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

3:15 p.m. - 4:00 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 45mdirect

C$ 1,389Air Canada

Wed, 25 Nov - Wed, 2 Dec

9:35 a.m. - 2:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

3:15 p.m. - 4:00 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

1h 45mdirect

C$ 1,389Air Canada

Tue, 24 Nov - Tue, 1 Dec

9:15 a.m. - 11:39 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 24mdirect

2:15 p.m. - 4:36 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 21mdirect

C$ 1,389Air Canada

Fri, 2 Apr - Tue, 6 Apr

9:35 a.m. - 2:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

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

1h 35mdirect

C$ 1,389Air Canada

Wed, 11 Nov - Mon, 16 Nov

9:35 a.m. - 2:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

3h 48mdirect

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

1h 35mdirect

C$ 1,420United Airlines

Sat, 14 Nov - Sun, 15 Nov

9:15 a.m. - 11:39 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 24mdirect

2:15 p.m. - 4:36 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 21mdirect

C$ 1,460United Airlines

Fri, 2 Apr - Tue, 6 Apr

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Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

Porter Airlines

31 Oct

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

7h 07m

1 stop

YWG9:57 p.m.Winnipeg

10 Nov

YWG7:00 a.m.Winnipeg

7h 37m

1 stop

ORD1:37 p.m.Chicago O'Hare Intl

C$ 867

Porter Airlines

31 Oct

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

7h 07m

1 stop

YWG9:57 p.m.Winnipeg

9 Nov

YWG7:00 a.m.Winnipeg

7h 37m

1 stop

ORD1:37 p.m.Chicago O'Hare Intl

C$ 877

Porter Airlines

11 Nov

ORD9:42 a.m.Chicago O'Hare Intl

25h 00m

1 stop

YWG11:42 a.m.Winnipeg

16 Nov

YWG7:00 a.m.Winnipeg

7h 37m

1 stop

ORD1:37 p.m.Chicago O'Hare Intl

C$ 884

American Airlines flights from Chicago to Winnipeg

Our best American Airlines deals on Chicago to Winnipeg flight tickets

American Airlines

10 Nov

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

8h 02m

1 stop

YWG11:52 p.m.Winnipeg

17 Nov

YWG7:00 a.m.Winnipeg

6h 01m

1 stop

ORD12:01 p.m.Chicago O'Hare Intl

C$ 980

American Airlines

4 Nov

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

7h 02m

1 stop

YWG10:52 p.m.Winnipeg

11 Nov

YWG7:00 a.m.Winnipeg

7h 37m

1 stop

ORD1:37 p.m.Chicago O'Hare Intl

C$ 983

American Airlines

4 Nov

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

8h 02m

1 stop

YWG11:52 p.m.Winnipeg

11 Nov

YWG7:00 a.m.Winnipeg

7h 37m

1 stop

ORD1:37 p.m.Chicago O'Hare Intl

C$ 985

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 15/1

6:00 a.m.-3:40 p.m.

1 stop8h 40m

Winnipeg

Sun 17/1

9:35 p.m.-10:23 p.m.

2 stops25h 48m

C$ 645

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 26/11

7:49 a.m.-2:10 a.m.

2 stops17h 21m

Winnipeg

Sun 29/11

7:55 p.m.-4:40 p.m.

1 stop21h 45m

C$ 670

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 26/11

6:20 p.m.-11:15 a.m.

1 stop15h 55m

Winnipeg

Sun 29/11

7:55 p.m.-10:35 a.m.

1 stop15h 40m

C$ 683

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 10/11

7:35 p.m.-11:55 p.m.

2 stops27h 20m

Winnipeg

Tue 17/11

9:35 p.m.-5:30 p.m.

2 stops20h 55m

C$ 693

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 10/11

7:35 p.m.-2:10 a.m.

2 stops29h 35m

Winnipeg

Tue 17/11

9:35 p.m.-4:07 p.m.

3 stops19h 32m

C$ 768

Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 15/1

6:00 a.m.-3:40 p.m.

1 stop8h 40m

Winnipeg

Sun 17/1

9:05 p.m.-10:40 a.m.

1 stop14h 35m

C$ 784

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 21/11

5:26 p.m.-9:45 p.m.

2 stops27h 19m

Winnipeg

Wed 25/11

9:35 p.m.-12:44 p.m.

2 stops16h 09m

C$ 791

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 28/11

8:40 p.m.-1:05 p.m.

1 stop15h 25m

Winnipeg

Sat 5/12

6:00 a.m.-6:58 p.m.

1 stop13h 58m

C$ 804

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 5/11

7:50 p.m.-2:10 a.m.

2 stops29h 20m

Winnipeg

Thu 12/11

10:00 a.m.-5:35 p.m.

2 stops8h 35m

C$ 807

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 28/11

8:40 p.m.-1:05 p.m.

1 stop15h 25m

Winnipeg

Sat 5/12

6:00 a.m.-6:52 p.m.

2 stops13h 52m

C$ 812

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 Chicago to Winnipeg

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

Other information

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

Prices are currently typical for flights on this route.

Typical prices usually range from C$ 635 to C$ 1,163.
The lowest price recently found on this route was C$ 645.

What is the cheapest month to fly to Winnipeg?

The cheapest month to fly to Winnipeg from Chicago is in September. Flight prices, which tend to average around C$ 729, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of September, then departing from Chicago during the month March is also very affordable. Most momondo users find prices during this month for around C$ 751.

What is the cheapest Chicago to Winnipeg flight route?

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

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

There are 2 cabin classes available to choose from on Chicago to Winnipeg 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 Chicago to Winnipeg flights?

You could potentially save up to 41% on your flight if you consider stops on a Chicago to Winnipeg flight.

How have Chicago to Winnipeg flight prices changed over time?

As of October 2026, prices for Chicago to Winnipeg flights are approximately 30% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Winnipeg

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

Estimated round-trip price

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

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

Best price found	C$ 276
Fastest flight time	2h 24m
Direct flights	Every day
Airports in Winnipeg	1 airport

The best one-way flight to Winnipeg from Chicago in the past 72 hours is C$ 276. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is C$ 645.

The fastest flight from Chicago to Winnipeg takes 2h 24m

Direct flights go from Chicago to Winnipeg every day.

There is 1 airport in Winnipeg. From Chicago there are direct flights to Winnipeg (YWG).

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Frequently asked questions about flying from Chicago to Winnipeg

How far is Chicago to Winnipeg by plane?
A flight from Chicago to Winnipeg will travel around 1153.0 km. Typically, this will take 2h 24m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to Winnipeg Airport?
Prices for flights from Chicago to Winnipeg Airport are updated daily.
How old do you have to be to fly from Chicago to Winnipeg Airport?
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 Chicago to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The necessary travel and health documents for your Winnipeg Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Winnipeg?
Based on momondo bookings for flights between Chicago and Winnipeg, the leading plane model is Embraer 175 (Enhanced Winglets), making up 74.07% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 7.41%, Boeing 777-300ER with 7.41%, and Boeing 777-300 with 7.41%.

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Winnipeg for you.

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

Yes. momondo enables you to select and highlight flights to Winnipeg from Chicago with this policy.

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

momondo helps you find the best flight between Chicago and Winnipeg by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Winnipeg, momondo offers a useful price alert feature which will track prices for flights to Winnipeg from Chicago and alert you when they change.

An easier way to manage your Winnipeg trip

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Cheap flights from Chicago to Winnipeg from C$ 276

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Winnipeg departing on 18/1. 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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Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

American Airlines flights from Chicago to Winnipeg

Our best American Airlines deals on Chicago to Winnipeg flight tickets

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How to get the cheapest flight ticket from Chicago to Winnipeg

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

What is the cheapest month to fly to Winnipeg?

What is the cheapest Chicago to Winnipeg flight route?

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

Can stopping save me money on Chicago to Winnipeg flights?

How have Chicago to Winnipeg flight prices changed over time?

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

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

When to book flights from Chicago to Winnipeg

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

Best price found

Fastest flight time

Direct flights

Airports in Winnipeg

Frequently asked questions about flying from Chicago to Winnipeg

Travelling to a place near Winnipeg?

Why use momondo?

An easier way to manage your Winnipeg 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Canada

Airports servicing Manitoba

Cabin classes currently available on flights to Winnipeg

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

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

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According to popular flight searches on momondo this year

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