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Cheap flights from Chicago to Winnipeg from C$ 200

1 adult
1 adult, Economy, 0 bags

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  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 416WestJet
Tue, 29 Sep - Tue, 6 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 422WestJet
Fri, 9 Oct - Mon, 12 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 423WestJet
Sun, 11 Oct - Sun, 18 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 439WestJet
Sun, 11 Oct - Sun, 18 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 443WestJet
Fri, 2 Oct - Mon, 5 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 461WestJet
Tue, 29 Sep - Tue, 6 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
6:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
10h 40m1 stop Calgary
C$ 476WestJet
Fri, 2 Oct - Thu, 15 Oct
Multiple Airlines Logo
7:11 a.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
17h 44m2 stops Fort Lauderdale Toronto Pearson Intl
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 490Multiple Airlines
Fri, 2 Oct - Mon, 5 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:10 p.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
21h 30m1 stop Calgary
C$ 493WestJet
Fri, 2 Oct - Sat, 10 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
9:05 p.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
19h 35m1 stop Calgary
C$ 500WestJet
Fri, 2 Oct - Mon, 5 Oct

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Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets
Porter Airlines
1 Oct
MDW11:45 a.m.Chicago Midway
8h 05m
1 stop
YWG7:50 p.m.Winnipeg
4 Oct
YWG8:45 p.m.Winnipeg
14h 15m
1 stop
MDW11:00 a.m.Chicago Midway
C$ 790
Porter Airlines
13 Sep
MDW3:20 p.m.Chicago Midway
19h 00m
2 stops
YWG10:20 a.m.Winnipeg
22 Sep
YWG8:45 p.m.Winnipeg
14h 15m
1 stop
MDW11:00 a.m.Chicago Midway
C$ 820
Porter Airlines
26 Sep
MDW3:20 p.m.Chicago Midway
26h 38m
2 stops
YWG5:58 p.m.Winnipeg
29 Sep
YWG11:15 a.m.Winnipeg
23h 45m
2 stops
MDW11:00 a.m.Chicago Midway
C$ 923

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
29 Sep
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
6 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 416
WestJet
9 Oct
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
12 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 422
WestJet
11 Oct
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
18 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 423

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.

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Price

Cheapest round-trip
Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 29/9

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

1 stop7h 25m

Winnipeg

Tue 6/10

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

1 stop9h 40m

C$ 416

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 9/10

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

1 stop7h 25m

Winnipeg

Mon 12/10

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

1 stop9h 40m

C$ 422

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 11/10

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

1 stop7h 25m

Winnipeg

Sun 18/10

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

1 stop9h 40m

C$ 423

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 11/10

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

1 stop7h 25m

Winnipeg

Sun 18/10

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

1 stop9h 40m

C$ 439

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 2/10

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

1 stop7h 25m

Winnipeg

Mon 5/10

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

1 stop9h 40m

C$ 443

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 29/9

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

1 stop7h 25m

Winnipeg

Tue 6/10

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

1 stop9h 40m

C$ 461

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 2/10

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

1 stop7h 25m

Winnipeg

Thu 15/10

6:00 a.m.-4:40 p.m.

1 stop10h 40m

C$ 476

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 2/10

7:11 a.m.-12:55 a.m.

2 stops17h 44m

Winnipeg

Mon 5/10

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

1 stop9h 40m

C$ 490

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 2/10

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

1 stop7h 25m

Winnipeg

Sat 10/10

7:10 p.m.-4:40 p.m.

1 stop21h 30m

C$ 493

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 2/10

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

1 stop7h 25m

Winnipeg

Mon 5/10

9:05 p.m.-4:40 p.m.

1 stop19h 35m

C$ 500

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 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$ 604, 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 October is also very affordable. Most momondo users find prices during this month for around C$ 665.

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 2 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?

As of September 2026, prices for Chicago to Winnipeg flights are approximately 109% 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$ 200

Fastest flight time

2h 24m

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$ 200. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is C$ 416.
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
Portage la Prairie
Morden
Selkirk

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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