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Cheap flights from Chicago to Winnipeg from C$ 160

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 4/2. 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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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.
6:15 a.m. - 3:08 p.m.MDW-YWG
8h 53m1 stop
7:30 a.m. - 3:43 p.m.YWG-MDW
8h 13m1 stop
C$ 405
Find Deal
Mon, 3 Feb - Mon, 10 Feb
6:40 a.m. - 3:10 p.m.MDW-YWG
8h 30m1 stop
7:30 a.m. - 3:43 p.m.YWG-MDW
8h 13m1 stop
C$ 443
Find Deal
Fri, 31 Jan - Mon, 3 Feb
5:30 p.m. - 2:30 p.m.ORD-YWG
21h 00m1 stop
8:30 a.m. - 4:44 p.m.YWG-ORD
8h 14m1 stop
C$ 563WestJet
Find Deal
Fri, 30 May - Mon, 2 Jun
4:45 p.m. - 12:44 a.m.ORD-YWG
7h 59m1 stop
5:30 p.m. - 4:44 p.m.YWG-ORD
23h 14m1 stop
C$ 622WestJet
Find Deal
Sun, 20 Apr - Sun, 4 May
12:51 p.m. - 7:13 p.m.ORD-YWG
6h 22m1 stop
6:45 a.m. - 2:45 p.m.YWG-ORD
8h 00m2 stops
C$ 727Air Canada
Find Deal
Thu, 30 Jan - Mon, 3 Feb
12:51 p.m. - 7:13 p.m.ORD-YWG
6h 22m1 stop
6:45 a.m. - 2:45 p.m.YWG-ORD
8h 00m2 stops
C$ 733Air Canada
Find Deal
Thu, 30 Jan - Mon, 3 Feb
1:00 p.m. - 3:24 p.m.ORD-YWG
2h 24mdirect
2:15 p.m. - 4:36 p.m.YWG-ORD
2h 21mdirect
C$ 776United Airlines
Find Deal
Fri, 30 May - Mon, 2 Jun
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$ 782United Airlines
Find Deal
Thu, 30 Jan - Mon, 3 Feb
10:19 a.m. - 4:47 p.m.MDW-YWG
6h 28m1 stop
6:40 a.m. - 5:43 p.m.YWG-MDW
11h 03m1 stop
C$ 818Delta
Find Deal
Thu, 30 Jan - Mon, 3 Feb
10:10 a.m. - 4:47 p.m.ORD-YWG
6h 37m1 stop
12:45 p.m. - 11:59 p.m.YWG-ORD
11h 14m2 stops
C$ 825Delta
Find Deal
Thu, 23 Jan - Mon, 27 Jan
5:31 p.m. - 3:08 p.m.MDW-YWG
21h 37m1 stop
C$ 160
Find Deal
Tue, 4 Feb
6:15 a.m. - 3:10 p.m.MDW-YWG
8h 55m1 stop
C$ 180
Find Deal
Mon, 13 Jan
12:58 p.m. - 3:28 p.m.ORD-YWG
2h 30mdirect
C$ 355United Airlines
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Fri, 28 Feb
7:20 a.m. - 4:28 p.m.ORD-YWG
9h 08m1 stop
C$ 356Air Canada
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Tue, 4 Feb
6:15 a.m. - 7:10 p.m.ORD-YWG
12h 55m2 stops
C$ 358WestJet
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Sun, 12 Jan
1:05 p.m. - 6:04 p.m.MDW-YWG
28h 59m2 stops
C$ 412Porter Airlines
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Sun, 12 Jan
1:05 p.m. - 6:04 p.m.MDW-YWG
28h 59m2 stops
C$ 438Porter Airlines
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Sat, 11 Jan
10:10 a.m. - 11:18 p.m.ORD-YWG
13h 08m2 stops
C$ 454WestJet
Find Deal
Fri, 28 Feb
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 463United Airlines
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Tue, 7 Jan
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 602Air Canada
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Thu, 2 Jan
5:50 p.m. - 11:43 p.m.ORD-YWG
5h 53m1 stop
12:20 p.m. - 11:30 a.m.YWG-ORD
23h 10m2 stops
C$ 1,316WestJet
Find Deal
Wed, 25 Dec - Fri, 3 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$ 1,325Air Canada
Find Deal
Wed, 25 Dec - Sat, 4 Jan
6:28 p.m. - 8:28 a.m.ORD-YWG
14h 00m1 stop
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 1,332Air Canada
Find Deal
Wed, 25 Dec - Sat, 4 Jan
4:50 p.m. - 11:43 p.m.MDW-YWG
6h 53m1 stop
11:35 a.m. - 10:30 a.m.YWG-MDW
22h 55m2 stops
C$ 1,375
Find Deal
Wed, 25 Dec - Fri, 3 Jan
3:18 p.m. - 11:43 p.m.ORD-YWG
8h 25m1 stop
6:55 a.m. - 6:48 p.m.YWG-ORD
11h 53m2 stops
C$ 1,440Delta
Find Deal
Wed, 25 Dec - Fri, 3 Jan
5:50 p.m. - 11:43 p.m.ORD-YWG
5h 53m1 stop
6:55 a.m. - 2:38 p.m.YWG-ORD
7h 43m1 stop
C$ 1,446Delta
Find Deal
Wed, 25 Dec - Sat, 4 Jan
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
4:30 p.m. - 11:59 p.m.YWG-ORD
7h 29m1 stop
C$ 1,486United Airlines
Find Deal
Wed, 25 Dec - Fri, 3 Jan
9:15 p.m. - 6:04 p.m.ORD-YWG
20h 49m2 stops
2:40 p.m. - 10:45 a.m.YWG-ORD
20h 05m3 stops
C$ 1,540
Find Deal
Tue, 24 Dec - Thu, 26 Dec
5:35 p.m. - 6:04 p.m.MDW-YWG
24h 29m2 stops
11:35 a.m. - 10:20 a.m.YWG-MDW
22h 45m2 stops
C$ 1,894Porter Airlines
Find Deal
Wed, 25 Dec - Sat, 4 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$ 2,993United Airlines
Find Deal
Wed, 25 Dec - Fri, 3 Jan
1:00 p.m. - 3:24 p.m.ORD-YWG
2h 24mdirect
2:15 p.m. - 4:36 p.m.YWG-ORD
2h 21mdirect
C$ 776United Airlines
Find Deal
Fri, 30 May - Mon, 2 Jun
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$ 782United Airlines
Find Deal
Thu, 30 Jan - Mon, 3 Feb
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$ 785United Airlines
Find Deal
Fri, 31 Jan - Mon, 3 Feb
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$ 822Air Canada
Find Deal
Thu, 23 Jan - Mon, 27 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$ 852United Airlines
Find Deal
Mon, 3 Feb - Mon, 10 Feb
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$ 884Air Canada
Find Deal
Sat, 18 Jan - Sat, 25 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$ 945United Airlines
Find Deal
Sat, 18 Jan - Sat, 25 Jan
1:00 p.m. - 3:24 p.m.ORD-YWG
2h 24mdirect
2:15 p.m. - 4:36 p.m.YWG-ORD
2h 21mdirect
C$ 993Air Canada
Find Deal
Fri, 20 Jun - Sun, 22 Jun
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$ 1,131Air Canada
Find Deal
Thu, 2 Jan - Mon, 6 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$ 1,247
Find Deal
Fri, 3 Jan - Tue, 7 Jan

Air Canada flights from Chicago to Winnipeg

Our best Air Canada deals on Chicago to Winnipeg flight tickets
Air Canada
30 Jan
ORD12:51 p.m.Chicago O'Hare Intl
6h 22m
1 stop
YWG7:13 p.m.Winnipeg
3 Feb
YWG6:45 a.m.Winnipeg
8h 00m
2 stops
ORD2:45 p.m.Chicago O'Hare Intl
Air Canada
30 Jan
ORD12:51 p.m.Chicago O'Hare Intl
6h 22m
1 stop
YWG7:13 p.m.Winnipeg
3 Feb
YWG6:45 a.m.Winnipeg
8h 00m
2 stops
ORD2:45 p.m.Chicago O'Hare Intl
Air Canada
31 Jan
ORD7:20 a.m.Chicago O'Hare Intl
9h 08m
1 stop
YWG4:28 p.m.Winnipeg
3 Feb
YWG6:45 a.m.Winnipeg
8h 00m
2 stops
ORD2:45 p.m.Chicago O'Hare Intl

Delta flights from Chicago to Winnipeg

Our best Delta deals on Chicago to Winnipeg flight tickets
Delta
30 Jan
MDW10:19 a.m.Chicago Midway
6h 28m
1 stop
YWG4:47 p.m.Winnipeg
3 Feb
YWG6:40 a.m.Winnipeg
11h 03m
1 stop
MDW5:43 p.m.Chicago Midway
Delta
30 Jan
MDW10:19 a.m.Chicago Midway
6h 28m
1 stop
YWG4:47 p.m.Winnipeg
3 Feb
YWG6:40 a.m.Winnipeg
6h 25m
2 stops
MDW1:05 p.m.Chicago Midway
Delta
23 Jan
ORD6:45 a.m.Chicago O'Hare Intl
10h 02m
2 stops
YWG4:47 p.m.Winnipeg
27 Jan
YWG12:45 p.m.Winnipeg
8h 30m
2 stops
ORD9:15 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 typical price of a round-trip flight between Chicago and Winnipeg?

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$ 619, 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 May is also very affordable. Most momondo users find prices during this month for around C$ 664.

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

Our data shows that Thursday is the least expensive day to fly to Winnipeg. Tickets to fly out on this day can be as low as C$ 0. Be sure to avoid booking your departure on a Tuesday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Tuesday is C$ 1,059.

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

In the evening is the cheapest time of day to fly from Chicago to Winnipeg when you can find flight prices for as low as C$ 0. Flying to Winnipeg in the evening is an ideal time because this is during off-peak travel hours. Flights to Winnipeg are more costly in the morning, with an average ticket price of C$ 992. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Winnipeg flight route?

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

How far in advance should I book a flight to Winnipeg?

Most flyers found that booking tickets 32 days in advance of their planned departure date is the best time to get cheap flights to Winnipeg. During this timeframe, flight prices are around C$ 828. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Winnipeg from Chicago for as low as C$ 324 on momondo.

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

There are 1 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 55% 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 December 2024, prices for Chicago to Winnipeg flights are approximately 0% more expensive 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$ 160

Fastest flight time

2h 24m

Direct flights

Mon, Tue, Wed, 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$ 160. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is C$ 405.
The fastest flight from Chicago to Winnipeg takes 2h 24m
Direct flights go from Chicago to Winnipeg on Monday, Tuesday, Wednesday, 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 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 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$ 506Free CancellationRating
7.0
8,413 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$ 689 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.


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