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Cheap flights from Chicago to Winnipeg from C$ 140

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 9/7. 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

WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 314WestJet
Find Deal
Wed, 17 Sep - Sun, 21 Sep
WestJet Logo
5:30 p.m. - 9:30 p.m.ORD-YWG
28h 00m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 368WestJet
Find Deal
Thu, 16 Oct - Fri, 24 Oct
 Logo
1:40 p.m. - 9:56 p.m.ORD-YWG
8h 16m1 stop
 Logo
9:00 a.m. - 9:30 p.m.YWG-ORD
12h 30m1 stop
C$ 383
Find Deal
Wed, 9 Jul - Fri, 11 Jul
 Logo
6:02 p.m. - 12:31 a.m.ORD-YWG
30h 29m2 stops
 Logo
9:00 a.m. - 7:04 a.m.YWG-ORD
22h 04m1 stop
C$ 395
Find Deal
Wed, 9 Jul - Fri, 11 Jul
Air Canada Logo
7:58 p.m. - 10:33 p.m.ORD-YWG
2h 35mdirect
Air Canada Logo
5:00 a.m. - 1:13 p.m.YWG-ORD
8h 13m1 stop
C$ 737Air Canada
Find Deal
Tue, 29 Jul - Tue, 5 Aug
Porter Airlines Logo
5:20 p.m. - 10:46 p.m.MDW-YWG
29h 26m2 stops
Porter Airlines Logo
11:45 a.m. - 8:45 a.m.YWG-MDW
21h 00m2 stops
C$ 741Porter Airlines
Find Deal
Wed, 16 Jul - Wed, 23 Jul
Air Canada Logo
9:50 a.m. - 3:58 p.m.ORD-YWG
6h 08m1 stop
Air Canada Logo
5:15 a.m. - 10:58 a.m.YWG-ORD
5h 43m1 stop
C$ 750Air Canada
Find Deal
Tue, 28 Oct - Fri, 7 Nov
United Airlines Logo
7:58 p.m. - 10:33 p.m.ORD-YWG
2h 35mdirect
United Airlines Logo
7:00 a.m. - 9:31 a.m.YWG-ORD
2h 31mdirect
C$ 751United Airlines
Find Deal
Wed, 30 Jul - Sun, 3 Aug
United Airlines Logo
1:02 p.m. - 3:31 p.m.ORD-YWG
2h 29mdirect
United Airlines Logo
7:00 a.m. - 9:31 a.m.YWG-ORD
2h 31mdirect
C$ 752United Airlines
Find Deal
Wed, 30 Jul - Sun, 3 Aug
Porter Airlines Logo
9:15 a.m. - 8:46 p.m.MDW-YWG
11h 31m2 stops
Porter Airlines Logo
11:45 a.m. - 8:19 a.m.YWG-MDW
20h 34m2 stops
C$ 760Porter Airlines
Find Deal
Wed, 17 Sep - Sun, 21 Sep

United Airlines flights from Chicago to Winnipeg

Our best United Airlines deals on Chicago to Winnipeg flight tickets
United Airlines
30 Jul
ORD7:58 p.m.Chicago O'Hare Intl
2h 35m
YWG10:33 p.m.Winnipeg
3 Aug
YWG7:00 a.m.Winnipeg
2h 31m
ORD9:31 a.m.Chicago O'Hare Intl
United Airlines
30 Jul
ORD1:02 p.m.Chicago O'Hare Intl
2h 29m
YWG3:31 p.m.Winnipeg
3 Aug
YWG7:00 a.m.Winnipeg
2h 31m
ORD9:31 a.m.Chicago O'Hare Intl
United Airlines
30 Jul
ORD5:00 a.m.Chicago O'Hare Intl
8h 09m
1 stop
YWG1:09 p.m.Winnipeg
3 Aug
YWG7:00 a.m.Winnipeg
2h 31m
ORD9:31 a.m.Chicago O'Hare Intl

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
17 Sep
ORD1:40 p.m.Chicago O'Hare Intl
7h 45m
1 stop
YWG9:25 p.m.Winnipeg
21 Sep
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
WestJet
16 Oct
ORD5:30 p.m.Chicago O'Hare Intl
28h 00m
1 stop
YWG9:30 p.m.Winnipeg
24 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
WestJet
30 Jul
ORD1:40 p.m.Chicago O'Hare Intl
8h 16m
1 stop
YWG9:56 p.m.Winnipeg
6 Aug
YWG9:05 p.m.Winnipeg
19h 39m
1 stop
ORD4:44 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 May. Flight prices, which tend to average around C$ 368, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of May, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around C$ 433.

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

Our data shows that Tuesday is the least expensive day to fly to Winnipeg. Tickets to fly out on this day can be as low as C$ 435. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Saturday is C$ 985.

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

In the morning is the cheapest time of day to fly from Chicago to Winnipeg when you can find flight prices for as low as C$ 436. Flying to Winnipeg in the morning is an ideal time because this is during off-peak travel hours. Flights to Winnipeg are more costly at noon, with an average ticket price of C$ 740. Departure times at noon 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

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 39% 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 June 2025, prices for Chicago to Winnipeg flights are approximately 6% 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$ 140

Fastest flight time

2h 29m

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$ 140. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is C$ 314.
The fastest flight from Chicago to Winnipeg takes 2h 29m
Direct flights go from Chicago to Winnipeg every day.
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 29m 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?


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$ 435Free CancellationRating
7.1
9,553 reviews
Search Air Canada flights
  • Air Canada Flights From Chicago to Winnipeg

    Air Canada flight deals from Chicago to Winnipeg start from C$ 320 round-trip. Over the 14 Air Canada flights for this route in a normal week, average airfare is usually C$ 725 round-trip - but some users have found much cheaper deals with momondo.


Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Portage la Prairie

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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