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Cheap flights from Chicago to Winnipeg from C$ 139

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 28/9. 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

Logo
5:30 p.m. - 11:26 a.m.ORD-YWG
17h 56m2 stops
Logo
9:00 a.m. - 5:21 p.m.YWG-ORD
8h 21m1 stop
C$ 312
Find Deal
Mon, 29 Sep - Mon, 6 Oct
WestJet Logo
5:30 p.m. - 11:10 p.m.ORD-YWG
29h 40m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 320WestJet
Find Deal
Fri, 17 Oct - Mon, 20 Oct
WestJet Logo
5:30 p.m. - 8:15 p.m.ORD-YWG
26h 45m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 323WestJet
Find Deal
Thu, 16 Oct - Fri, 24 Oct
WestJet Logo
5:30 p.m. - 11:26 a.m.ORD-YWG
17h 56m2 stops
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 334WestJet
Find Deal
Thu, 16 Oct - Fri, 24 Oct
Logo
5:30 p.m. - 11:41 a.m.ORD-YWG
18h 11m1 stop
Logo
9:00 a.m. - 5:21 p.m.YWG-ORD
8h 21m1 stop
C$ 340
Find Deal
Mon, 29 Sep - Mon, 6 Oct
United Airlines Logo
7:54 p.m. - 10:33 p.m.ORD-YWG
2h 39mdirect
United Airlines Logo
7:00 a.m. - 9:31 a.m.YWG-ORD
2h 31mdirect
C$ 530United Airlines
Find Deal
Thu, 11 Sep - Sun, 14 Sep
United Airlines Logo
7:54 p.m. - 10:33 p.m.ORD-YWG
2h 39mdirect
United Airlines Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
C$ 574United Airlines
Find Deal
Fri, 5 Sep - Wed, 10 Sep
Delta Logo
1:08 p.m. - 11:27 p.m.MDW-YWG
10h 19m2 stops
Delta Logo
8:35 a.m. - 5:35 p.m.YWG-MDW
9h 00m1 stop
C$ 595Delta
Find Deal
Sat, 13 Sep - Sat, 20 Sep
Delta Logo
1:08 p.m. - 11:27 p.m.MDW-YWG
10h 19m2 stops
Delta Logo
12:44 p.m. - 9:10 p.m.YWG-MDW
8h 26m2 stops
C$ 602Delta
Find Deal
Sat, 13 Sep - Sat, 20 Sep
Porter Airlines Logo
4:15 p.m. - 11:13 a.m.MDW-YWG
18h 58m2 stops
Porter Airlines Logo
4:25 p.m. - 10:05 a.m.YWG-MDW
17h 40m2 stops
C$ 859Porter Airlines
Find Deal
Fri, 31 Oct - Wed, 5 Nov

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
17 Oct
ORD5:30 p.m.Chicago O'Hare Intl
29h 40m
1 stop
YWG11:10 p.m.Winnipeg
20 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 320
Find similar
WestJet
16 Oct
ORD5:30 p.m.Chicago O'Hare Intl
26h 45m
1 stop
YWG8:15 p.m.Winnipeg
24 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 323
Find similar
WestJet
16 Oct
ORD5:30 p.m.Chicago O'Hare Intl
17h 56m
2 stops
YWG11:26 a.m.Winnipeg
24 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 334
Find similar

Delta flights from Chicago to Winnipeg

Our best Delta deals on Chicago to Winnipeg flight tickets
Delta
13 Sep
MDW1:08 p.m.Chicago Midway
10h 19m
2 stops
YWG11:27 p.m.Winnipeg
20 Sep
YWG8:35 a.m.Winnipeg
9h 00m
1 stop
MDW5:35 p.m.Chicago Midway
C$ 595
Find similar
Delta
13 Sep
MDW1:08 p.m.Chicago Midway
10h 19m
2 stops
YWG11:27 p.m.Winnipeg
20 Sep
YWG12:44 p.m.Winnipeg
8h 26m
2 stops
MDW9:10 p.m.Chicago Midway
C$ 602
Find similar
Delta
13 Sep
MDW9:20 a.m.Chicago Midway
7h 30m
1 stop
YWG4:50 p.m.Winnipeg
20 Sep
YWG6:40 a.m.Winnipeg
6h 23m
1 stop
MDW1:03 p.m.Chicago Midway
C$ 609
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 16 August 2025.
Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 29/9

5:30 p.m.-11:26 a.m.

2 stops17h 56m

Winnipeg

Mon 6/10

9:00 a.m.-5:21 p.m.

1 stop8h 21m

C$ 312

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 17/10

5:30 p.m.-11:10 p.m.

1 stop29h 40m

Winnipeg

Mon 20/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 320

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 16/10

5:30 p.m.-8:15 p.m.

1 stop26h 45m

Winnipeg

Fri 24/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 323

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 16/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

Winnipeg

Fri 24/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 334

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 29/9

5:30 p.m.-11:41 a.m.

1 stop18h 11m

Winnipeg

Mon 6/10

9:00 a.m.-5:21 p.m.

1 stop8h 21m

C$ 340

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 11/9

7:54 p.m.-10:33 p.m.

Nonstop2h 39m

Winnipeg

Sun 14/9

7:00 a.m.-9:31 a.m.

Nonstop2h 31m

C$ 530

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/9

7:54 p.m.-10:33 p.m.

Nonstop2h 39m

Winnipeg

Wed 10/9

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

C$ 574

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 13/9

1:08 p.m.-11:27 p.m.

2 stops10h 19m

Winnipeg

Sat 20/9

8:35 a.m.-5:35 p.m.

1 stop9h 00m

C$ 595

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 13/9

1:08 p.m.-11:27 p.m.

2 stops10h 19m

Winnipeg

Sat 20/9

12:44 p.m.-9:10 p.m.

2 stops8h 26m

C$ 602

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 31/10

4:15 p.m.-11:13 a.m.

2 stops18h 58m

Winnipeg

Wed 5/11

4:25 p.m.-10:05 a.m.

2 stops17h 40m

C$ 859

Flights are sorted by cheapest round-trip flights first.

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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 to Winnipeg?

The cheapest month to fly to Winnipeg from Chicago is in May. Flight prices, which tend to average around C$ 374, 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$ 440.

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$ 442. 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$ 1,002.

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$ 443. Flying to Winnipeg in the morning is an ideal time because this is during off-peak travel hours. Flights to Winnipeg are more costly in the evening, with an average ticket price of C$ 928. Departure times in the evening 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 50% on your flight if you consider stops on a Chicago to Winnipeg flight.

How have Chicago to Winnipeg flight prices changed over time?

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$ 139

Fastest flight time

2h 30m

Direct flights

Tue, Wed, 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$ 139. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is C$ 312.
The fastest flight from Chicago to Winnipeg takes 2h 30m
Direct flights go from Chicago to Winnipeg on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and Air Canada.
There is 1 airport near Winnipeg: Winnipeg (YWG)
Search flight deals

  • 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 39m 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$ 442Free CancellationRating
7.1
9,966 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 8 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
Morden

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

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