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Cheap flights from Chicago to Winnipeg from C$ 217

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 25/10. 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

Enter your travel dates to find the best prices.
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 498WestJet
Wed, 2 Sep - Sat, 5 Sep
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 532WestJet
Wed, 2 Sep - Sat, 5 Sep
Multiple Airlines Logo
10:15 a.m. - 9:45 a.m.
MDW
-
YWG
23h 30m
1 stop
Multiple Airlines Logo
6:05 p.m. - 9:40 a.m.
YWG
-
MDW
15h 35m
1 stop
C$ 553Multiple Airlines
Tue, 16 Jun - Mon, 22 Jun
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 557WestJet
Thu, 15 Oct - Mon, 19 Oct
Multiple Airlines Logo
10:15 a.m. - 9:45 a.m.
MDW
-
YWG
23h 30m
1 stop
Multiple Airlines Logo
8:45 p.m. - 9:40 a.m.
YWG
-
MDW
12h 55m
1 stop
C$ 561Multiple Airlines
Wed, 17 Jun - Sun, 21 Jun
Porter Airlines Logo
10:15 a.m. - 7:49 p.m.
MDW
-
YWG
9h 34m
1 stop
Porter Airlines Logo
8:45 p.m. - 9:40 a.m.
YWG
-
MDW
12h 55m
1 stop
C$ 568Porter Airlines
Tue, 16 Jun - Sun, 21 Jun
Multiple Airlines Logo
3:20 p.m. - 12:55 a.m.
MDW
-
YWG
9h 35m
1 stop
Multiple Airlines Logo
9:05 p.m. - 11:12 a.m.
YWG
-
MDW
14h 07m
2 stops
C$ 575Multiple Airlines
Thu, 4 Jun - Mon, 8 Jun
Multiple Airlines Logo
10:15 a.m. - 7:49 p.m.
MDW
-
YWG
9h 34m
1 stop
Multiple Airlines Logo
5:10 p.m. - 9:40 a.m.
YWG
-
MDW
16h 30m
1 stop
C$ 579Multiple Airlines
Tue, 16 Jun - Sat, 20 Jun
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
12:15 p.m. - 7:29 p.m.
YWG
-
ORD
7h 14m
1 stop
C$ 584Multiple Airlines
Mon, 29 Jun - Mon, 6 Jul
Porter Airlines Logo
10:15 a.m. - 7:49 p.m.
MDW
-
YWG
9h 34m
1 stop
Porter Airlines Logo
8:45 p.m. - 9:40 a.m.
YWG
-
MDW
12h 55m
1 stop
C$ 597Porter Airlines
Wed, 17 Jun - Fri, 19 Jun

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
2 Sep
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
5 Sep
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 498
WestJet
2 Sep
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
5 Sep
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 532
WestJet
15 Oct
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
19 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 557

Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets
Porter Airlines
16 Jun
MDW10:15 a.m.Chicago Midway
9h 34m
1 stop
YWG7:49 p.m.Winnipeg
21 Jun
YWG8:45 p.m.Winnipeg
12h 55m
1 stop
MDW9:40 a.m.Chicago Midway
C$ 568
Porter Airlines
17 Jun
MDW10:15 a.m.Chicago Midway
9h 34m
1 stop
YWG7:49 p.m.Winnipeg
19 Jun
YWG8:45 p.m.Winnipeg
12h 55m
1 stop
MDW9:40 a.m.Chicago Midway
C$ 597
Porter Airlines
19 Jun
MDW10:25 a.m.Chicago Midway
9h 24m
1 stop
YWG7:49 p.m.Winnipeg
23 Jun
YWG8:45 p.m.Winnipeg
12h 55m
1 stop
MDW9:40 a.m.Chicago Midway
C$ 602

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 17 May 2026.
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

Cheapest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 2/9

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sat 5/9

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 498

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 2/9

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sat 5/9

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 532

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 16/6

10:15 a.m.-9:45 a.m.

1 stop23h 30m

Winnipeg

Mon 22/6

6:05 p.m.-9:40 a.m.

1 stop15h 35m

C$ 553

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 15/10

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Mon 19/10

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 557

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 17/6

10:15 a.m.-9:45 a.m.

1 stop23h 30m

Winnipeg

Sun 21/6

8:45 p.m.-9:40 a.m.

1 stop12h 55m

C$ 561

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 16/6

10:15 a.m.-7:49 p.m.

1 stop9h 34m

Winnipeg

Sun 21/6

8:45 p.m.-9:40 a.m.

1 stop12h 55m

C$ 568

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 4/6

3:20 p.m.-12:55 a.m.

1 stop9h 35m

Winnipeg

Mon 8/6

9:05 p.m.-11:12 a.m.

2 stops14h 07m

C$ 575

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 16/6

10:15 a.m.-7:49 p.m.

1 stop9h 34m

Winnipeg

Sat 20/6

5:10 p.m.-9:40 a.m.

1 stop16h 30m

C$ 579
Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 29/6

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Mon 6/7

12:15 p.m.-7:29 p.m.

1 stop7h 14m

C$ 584

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 17/6

10:15 a.m.-7:49 p.m.

1 stop9h 34m

Winnipeg

Fri 19/6

8:45 p.m.-9:40 a.m.

1 stop12h 55m

C$ 597

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest 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 February. Flight prices, which tend to average around C$ 85, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of February, then departing from Chicago during the month October is also very affordable. Most momondo users find prices during this month for around C$ 111.

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$ 431. 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$ 924. 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

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?

As of May 2026, prices for Chicago to Winnipeg flights are approximately 43% cheaper 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

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Winnipeg

1 airport
The fastest flight from Chicago to Winnipeg takes 2h 24m
Direct flights go from Chicago to Winnipeg every day.
There is 1 airport in Winnipeg. From Chicago there are direct flights to Winnipeg (YWG).
Search flight deals

Frequently asked questions about flying from Chicago to Winnipeg

  • 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 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

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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