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Cheap flights from Chicago to Winnipeg from C$ 165

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 12/12. 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 Chicago to Winnipeg

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Winnipeg that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Winnipeg.

Cheap last-minute flights

Planning a quick getaway from Chicago to Winnipeg? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Winnipeg, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Winnipeg

Find recent round-trip train or bus tickets from Chicago to Winnipeg.

All round-trip flight deals to Winnipeg

The cheapest plane tickets to Winnipeg found on KAYAK recently.
7:39 p.m. - 9:09 p.m.ORD-YWG
25h 30m2 stops
7:30 a.m. - 9:10 p.m.YWG-ORD
13h 40m1 stop
C$ 472
Find Deal
Mon, 2 Dec - Mon, 9 Dec
7:39 p.m. - 3:10 p.m.ORD-YWG
19h 31m2 stops
11:35 a.m. - 9:37 a.m.YWG-ORD
22h 02m2 stops
C$ 508
Find Deal
Mon, 2 Dec - Mon, 9 Dec
9:50 a.m. - 5:08 p.m.ORD-YWG
7h 18m1 stop
11:00 a.m. - 7:32 p.m.YWG-ORD
8h 32m1 stop
C$ 664Air Canada
Find Deal
Thu, 12 Dec - Mon, 16 Dec
8:45 a.m. - 9:10 p.m.ORD-YWG
12h 25m1 stop
7:30 a.m. - 1:11 p.m.YWG-ORD
5h 41m1 stop
C$ 672Air Canada
Find Deal
Sat, 11 Jan - Sun, 19 Jan
7:59 p.m. - 11:45 a.m.ORD-YWG
15h 46m2 stops
5:37 p.m. - 9:58 p.m.YWG-ORD
4h 21m1 stop
C$ 701Delta
Find Deal
Mon, 16 Dec - Mon, 6 Jan
7:10 a.m. - 1:27 p.m.ORD-YWG
6h 17m1 stop
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 741United Airlines
Find Deal
Fri, 17 Jan - Sun, 19 Jan
12:05 p.m. - 9:09 p.m.MDW-YWG
9h 04m2 stops
11:35 a.m. - 10:20 a.m.YWG-MDW
22h 45m2 stops
C$ 742Porter Airlines
Find Deal
Fri, 13 Dec - Mon, 16 Dec
10:19 a.m. - 4:47 p.m.MDW-YWG
6h 28m1 stop
12:45 p.m. - 5:47 p.m.YWG-MDW
5h 02m1 stop
C$ 762Delta
Find Deal
Tue, 14 Jan - Sun, 19 Jan
7:10 a.m. - 1:27 p.m.ORD-YWG
6h 17m1 stop
7:30 a.m. - 7:53 a.m.YWG-ORD
24h 23m2 stops
C$ 767United Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
5:35 p.m. - 5:50 p.m.MDW-YWG
24h 15m1 stop
11:35 a.m. - 12:00 p.m.YWG-MDW
24h 25m2 stops
C$ 834Porter Airlines
Find Deal
Mon, 9 Dec - Fri, 13 Dec
6:15 p.m. - 3:10 p.m.MDW-YWG
20h 55m1 stop
C$ 165
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Thu, 12 Dec
2:03 p.m. - 12:43 a.m.MDW-YWG
10h 40m1 stop
C$ 183
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Sun, 12 Jan
12:05 p.m. - 11:40 p.m.MDW-YWG
11h 35m1 stop
C$ 265Porter Airlines
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Wed, 18 Dec
9:03 a.m. - 4:24 p.m.ORD-YWG
7h 21m1 stop
C$ 274Air Canada
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Sat, 12 Apr
8:45 a.m. - 9:10 p.m.ORD-YWG
12h 25m1 stop
C$ 290Air Canada
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Sat, 11 Jan
11:25 a.m. - 9:09 p.m.MDW-YWG
9h 44m2 stops
C$ 307Porter Airlines
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Thu, 12 Dec
12:58 p.m. - 3:28 p.m.ORD-YWG
2h 30mdirect
C$ 330United Airlines
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Fri, 28 Feb
7:15 a.m. - 1:03 p.m.ORD-YWG
5h 48m1 stop
C$ 332United Airlines
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Sat, 19 Apr
6:59 p.m. - 12:35 a.m.MDW-YWG
29h 36m2 stops
C$ 333WestJet
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Sat, 11 Jan
1:05 p.m. - 3:08 p.m.MDW-YWG
26h 03m1 stop
C$ 384WestJet
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Tue, 15 Apr
9:10 p.m. - 4:10 p.m.ORD-YWG
19h 00m2 stops
7:30 a.m. - 5:00 p.m.YWG-ORD
9h 30m1 stop
C$ 879
Find Deal
Thu, 21 Nov - Sun, 24 Nov
6:00 a.m. - 12:23 a.m.ORD-YWG
18h 23m2 stops
7:30 a.m. - 5:00 p.m.YWG-ORD
9h 30m1 stop
C$ 942
Find Deal
Fri, 22 Nov - Sun, 24 Nov
11:38 a.m. - 12:43 a.m.ORD-YWG
13h 05m1 stop
7:30 a.m. - 5:00 p.m.YWG-ORD
9h 30m1 stop
C$ 983
Find Deal
Fri, 22 Nov - Sun, 24 Nov
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
8:30 a.m. - 5:09 p.m.YWG-ORD
8h 39m1 stop
C$ 1,425Air Canada
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Thu, 21 Nov - Mon, 25 Nov
7:10 a.m. - 1:27 p.m.ORD-YWG
6h 17m1 stop
8:30 a.m. - 5:09 p.m.YWG-ORD
8h 39m1 stop
C$ 1,438Air Canada
Find Deal
Thu, 21 Nov - Mon, 25 Nov
11:15 a.m. - 9:09 p.m.MDW-YWG
9h 54m2 stops
11:35 a.m. - 10:20 a.m.YWG-MDW
22h 45m2 stops
C$ 1,604Porter Airlines
Find Deal
Thu, 21 Nov - Sun, 24 Nov
9:45 a.m. - 4:55 p.m.ORD-YWG
7h 10m1 stop
6:55 a.m. - 5:09 p.m.YWG-ORD
10h 14m2 stops
C$ 1,768Delta
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Thu, 21 Nov - Tue, 26 Nov
2:17 p.m. - 11:27 p.m.MDW-YWG
9h 10m1 stop
6:55 a.m. - 5:02 p.m.YWG-MDW
10h 07m2 stops
C$ 1,768Delta
Find Deal
Fri, 22 Nov - Mon, 25 Nov
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
C$ 1,901United Airlines
Find Deal
Thu, 21 Nov - Tue, 26 Nov
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
C$ 2,126United Airlines
Find Deal
Thu, 21 Nov - Sun, 24 Nov
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 728Air Canada
Find Deal
Thu, 9 Jan - Sun, 12 Jan
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 773Air Canada
Find Deal
Fri, 17 Jan - Sun, 19 Jan
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
C$ 818Air Canada
Find Deal
Fri, 13 Dec - Mon, 16 Dec
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 823Air Canada
Find Deal
Sat, 4 Jan - Sat, 11 Jan
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 833United Airlines
Find Deal
Mon, 16 Dec - Mon, 6 Jan
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
C$ 843United Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
C$ 878United Airlines
Find Deal
Mon, 9 Dec - Fri, 13 Dec
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 893United Airlines
Find Deal
Sat, 4 Jan - Sat, 11 Jan
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
C$ 1,074Air Canada
Find Deal
Mon, 2 Dec - Wed, 4 Dec
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 1,909United Airlines
Find Deal
Thu, 26 Dec - Tue, 7 Jan

Air Canada flights from Chicago to Winnipeg

Our best Air Canada deals on Chicago to Winnipeg flight tickets
Air Canada
12 Dec
ORD9:50 a.m.Chicago O'Hare Intl
7h 18m
1 stop
YWG5:08 p.m.Winnipeg
16 Dec
YWG11:00 a.m.Winnipeg
8h 32m
1 stop
ORD7:32 p.m.Chicago O'Hare Intl
Air Canada
11 Jan
ORD8:45 a.m.Chicago O'Hare Intl
12h 25m
1 stop
YWG9:10 p.m.Winnipeg
19 Jan
YWG7:30 a.m.Winnipeg
5h 41m
1 stop
ORD1:11 p.m.Chicago O'Hare Intl
Air Canada
16 Dec
ORD10:51 a.m.Chicago O'Hare Intl
6h 17m
1 stop
YWG5:08 p.m.Winnipeg
6 Jan
YWG7:30 a.m.Winnipeg
7h 21m
1 stop
ORD2:51 p.m.Chicago O'Hare Intl

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
16 Dec
MDW9:38 a.m.Chicago Midway
26h 07m
1 stop
YWG11:45 a.m.Winnipeg
6 Jan
YWG6:55 a.m.Winnipeg
10h 52m
1 stop
MDW5:47 p.m.Chicago Midway
WestJet
16 Dec
MDW2:15 p.m.Chicago Midway
26h 39m
1 stop
YWG4:54 p.m.Winnipeg
6 Jan
YWG5:37 p.m.Winnipeg
24h 10m
1 stop
MDW5:47 p.m.Chicago Midway
WestJet
10 Feb
ORD6:55 a.m.Chicago O'Hare Intl
8h 39m
2 stops
YWG3:34 p.m.Winnipeg
16 Feb
YWG6:20 a.m.Winnipeg
9h 36m
1 stop
ORD3:56 p.m.Chicago O'Hare Intl

See travel insights to Winnipeg from

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

What is the cheapest month to fly from Chicago to Winnipeg?

March. The cheapest time of year to fly to Winnipeg from Chicago is March. The most expensive is April.

What is the cheapest day to depart Chicago for Winnipeg?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Tuesday

When is the cheapest time to fly from Chicago to Winnipeg?

In the afternoon. Chicago to Winnipeg flights are approximately 40% more expensive in the morning than in the afternoon

What is the cheapest Chicago to Winnipeg flight route?

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

How far in advance should you book Chicago to Winnipeg flights?

45 days before. The cheapest time to buy a flight from Chicago to Winnipeg is approximately 45 days to departure

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?

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


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$ 165

Fastest flight time

2h 24m

Direct flights

Tue, Thu, Fri, Sat and Sun

Airports in Winnipeg

1 airport
The best one-way flight to Winnipeg from Chicago in the past 72 hours is C$ 165. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is C$ 472.
The fastest flight from Chicago to Winnipeg takes 2h 24m
Direct flights go from Chicago to Winnipeg on Tuesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and Air Canada.
There is 1 airport near Winnipeg: Winnipeg (YWG)

  • 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 32m 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 many operators does momondo search for flights from Chicago to Winnipeg Airport?

  • 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?

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


Best airlines flying from Chicago to Winnipeg

Compare and see reviews for airlines that fly from Chicago to Winnipeg with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 493Free CancellationRating
7.0
8,237 reviews
Search Air Canada flights
  • Air Canada Flights From Chicago to Winnipeg

    Air Canada flight deals from Chicago to Winnipeg start from C$ 352 round-trip. Over the 7 Air Canada flights for this route in a normal week, average airfare is usually C$ 690 round-trip - but some users have found much cheaper deals with momondo.


Why use momondo?

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

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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