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Cheap flights from Chicago to Winnipeg from C$ 113

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 4/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:01 p.m. - 12:41 a.m.ORD-YWG
32h 40m2 stops
Multiple Airlines Logo
7:30 a.m. - 6:46 p.m.YWG-ORD
11h 16m1 stop
C$ 277Multiple Airlines
Find Deal
Wed, 3 Dec - Wed, 10 Dec
Multiple Airlines Logo
1:56 p.m. - 3:07 p.m.MDW-YWG
25h 11m1 stop
Multiple Airlines Logo
7:30 a.m. - 2:40 p.m.YWG-MDW
7h 10m1 stop
C$ 326Multiple Airlines
Find Deal
Tue, 18 Nov - Fri, 21 Nov
Multiple Airlines Logo
6:00 p.m. - 3:09 p.m.ORD-YWG
21h 09m1 stop
Multiple Airlines Logo
4:10 p.m. - 10:39 a.m.YWG-ORD
18h 29m2 stops
C$ 382Multiple Airlines
Find Deal
Sat, 14 Feb - Thu, 19 Feb
Multiple Airlines Logo
6:00 p.m. - 3:09 p.m.ORD-YWG
21h 09m1 stop
Multiple Airlines Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
C$ 395Multiple Airlines
Find Deal
Sat, 14 Feb - Fri, 20 Feb
Multiple Airlines Logo
1:56 p.m. - 3:07 p.m.MDW-YWG
25h 11m1 stop
Multiple Airlines Logo
5:35 p.m. - 5:07 p.m.YWG-MDW
23h 32m2 stops
C$ 395Multiple Airlines
Find Deal
Tue, 18 Nov - Fri, 21 Nov
WestJet Logo
2:20 p.m. - 10:40 p.m.ORD-YWG
8h 20m1 stop
WestJet Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
C$ 403WestJet
Find Deal
Mon, 9 Mar - Fri, 13 Mar
WestJet Logo
2:20 p.m. - 10:40 p.m.ORD-YWG
8h 20m1 stop
WestJet Logo
5:00 a.m. - 4:37 p.m.YWG-ORD
11h 37m2 stops
C$ 554WestJet
Find Deal
Mon, 9 Mar - Fri, 13 Mar
Porter Airlines Logo
4:15 p.m. - 11:08 a.m.MDW-YWG
18h 53m2 stops
Porter Airlines Logo
4:25 p.m. - 10:05 a.m.YWG-MDW
17h 40m2 stops
C$ 1,168Porter Airlines
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Sun, 23 Nov - Sun, 30 Nov
Delta Logo
5:00 p.m. - 11:38 p.m.MDW-YWG
6h 38m1 stop
Delta Logo
11:53 a.m. - 6:37 p.m.YWG-MDW
6h 44m1 stop
C$ 1,483Delta
Find Deal
Sat, 14 Feb - Thu, 19 Feb
Delta Logo
11:48 a.m. - 4:55 p.m.MDW-YWG
5h 07m1 stop
Delta Logo
12:35 p.m. - 5:19 p.m.YWG-MDW
4h 44m1 stop
C$ 1,739Delta
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Sat, 20 Dec - Sat, 27 Dec

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
9 Mar
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
13 Mar
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
C$ 403
Find similar
WestJet
9 Mar
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
13 Mar
YWG5:00 a.m.Winnipeg
11h 37m
2 stops
ORD4:37 p.m.Chicago O'Hare Intl
C$ 554
Find similar
WestJet
22 Nov
ORD8:50 a.m.Chicago O'Hare Intl
8h 09m
1 stop
YWG4:59 p.m.Winnipeg
23 Nov
YWG5:49 p.m.Winnipeg
17h 45m
1 stop
ORD11:34 a.m.Chicago O'Hare Intl
C$ 703
Find similar

United Airlines flights from Chicago to Winnipeg

Our best United Airlines deals on Chicago to Winnipeg flight tickets
United Airlines
13 Nov
ORD1:00 p.m.Chicago O'Hare Intl
7h 56m
1 stop
YWG8:56 p.m.Winnipeg
20 Nov
YWG2:20 p.m.Winnipeg
2h 41m
ORD5:01 p.m.Chicago O'Hare Intl
C$ 1,460
Find similar
United Airlines
13 Nov
ORD9:22 a.m.Chicago O'Hare Intl
2h 35m
YWG11:57 a.m.Winnipeg
20 Nov
YWG2:20 p.m.Winnipeg
2h 41m
ORD5:01 p.m.Chicago O'Hare Intl
C$ 1,818
Find similar
United Airlines
11 Nov
ORD9:22 a.m.Chicago O'Hare Intl
2h 35m
YWG11:57 a.m.Winnipeg
14 Nov
YWG2:20 p.m.Winnipeg
2h 41m
ORD5:01 p.m.Chicago O'Hare Intl
C$ 2,457
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 6 November 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

Wed 3/12

4:01 p.m.-12:41 a.m.

2 stops32h 40m

Winnipeg

Wed 10/12

7:30 a.m.-6:46 p.m.

1 stop11h 16m

C$ 276

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 18/11

1:56 p.m.-3:07 p.m.

1 stop25h 11m

Winnipeg

Fri 21/11

7:30 a.m.-2:40 p.m.

1 stop7h 10m

C$ 326

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 14/2

6:00 p.m.-3:09 p.m.

1 stop21h 09m

Winnipeg

Thu 19/2

4:10 p.m.-10:39 a.m.

2 stops18h 29m

C$ 382

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 14/2

6:00 p.m.-3:09 p.m.

1 stop21h 09m

Winnipeg

Fri 20/2

6:15 a.m.-1:35 p.m.

1 stop7h 20m

C$ 395

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 18/11

1:56 p.m.-3:07 p.m.

1 stop25h 11m

Winnipeg

Fri 21/11

5:35 p.m.-5:07 p.m.

2 stops23h 32m

C$ 395

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

Winnipeg

Fri 13/3

6:15 a.m.-1:35 p.m.

1 stop7h 20m

C$ 403

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

Winnipeg

Fri 13/3

5:00 a.m.-4:37 p.m.

2 stops11h 37m

C$ 554

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 23/11

4:15 p.m.-11:08 a.m.

2 stops18h 53m

Winnipeg

Sun 30/11

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

2 stops17h 40m

C$ 1,168

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 14/2

5:00 p.m.-11:38 p.m.

1 stop6h 38m

Winnipeg

Thu 19/2

11:53 a.m.-6:37 p.m.

1 stop6h 44m

C$ 1,483

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 20/12

11:48 a.m.-4:55 p.m.

1 stop5h 07m

Winnipeg

Sat 27/12

12:35 p.m.-5:19 p.m.

1 stop4h 44m

C$ 1,739

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 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$ 382, 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$ 450.

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$ 452. 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$ 1,024.

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$ 452. 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$ 948. 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 is only 1 cabin class 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 49% 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

Fastest flight time

2h 24m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Winnipeg

1 airport
The fastest flight from Chicago to Winnipeg takes 2h 24m
Direct flights go from Chicago to Winnipeg on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Winnipeg: Winnipeg (YWG)
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  • How far is Chicago to Winnipeg by plane?

    A flight from Chicago to Winnipeg will travel around 1153.0 km. Typically, this will take 4h 42m 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?

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Morden
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.

An easier way to manage your Winnipeg trip

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