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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 218

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago O'Hare Intl Airport 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$ 453WestJet
Thu, 15 Oct - Mon, 19 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$ 456WestJet
Fri, 2 Oct - Sun, 4 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$ 470WestJet
Mon, 5 Oct - Mon, 12 Oct
Multiple Airlines Logo
8:04 a.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
16h 51m2 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$ 500Multiple Airlines
Thu, 15 Oct - Mon, 19 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$ 511WestJet
Thu, 15 Oct - Wed, 21 Oct
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
Multiple Airlines Logo
9:35 p.m. - 12:51 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
15h 16m2 stops Calgary Atlanta Hartsfield-Jackson
C$ 528Multiple Airlines
Fri, 23 Oct - Mon, 26 Oct
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
Multiple Airlines Logo
7:00 a.m. - 2:20 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
7h 20m1 stop Toronto Pearson Intl
C$ 532Multiple Airlines
Fri, 23 Oct - Fri, 30 Oct
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
Multiple Airlines Logo
9:20 a.m. - 4:18 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
6h 58m1 stop Toronto Pearson Intl
C$ 535Multiple Airlines
Tue, 29 Sep - Fri, 2 Oct
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
Multiple Airlines Logo
7:00 a.m. - 2:20 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
7h 20m1 stop Toronto Pearson Intl
C$ 538Multiple Airlines
Thu, 22 Oct - Thu, 29 Oct
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
Multiple Airlines Logo
9:20 a.m. - 4:18 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
6h 58m1 stop Toronto Pearson Intl
C$ 542Multiple Airlines
Thu, 1 Oct - Fri, 2 Oct

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Air Canada flights from Chicago O'Hare Intl Airport to Winnipeg

Our best Air Canada deals on Chicago O'Hare Intl Airport to Winnipeg flight tickets
Air Canada
4 Nov
ORD1:57 p.m.Chicago O'Hare Intl
7h 17m
1 stop
YWG9:14 p.m.Winnipeg
11 Nov
YWG12:45 p.m.Winnipeg
7h 13m
1 stop
ORD7:58 p.m.Chicago O'Hare Intl
C$ 723
Air Canada
4 Nov
ORD1:57 p.m.Chicago O'Hare Intl
7h 17m
1 stop
YWG9:14 p.m.Winnipeg
11 Nov
YWG12:45 p.m.Winnipeg
7h 13m
1 stop
ORD7:58 p.m.Chicago O'Hare Intl
C$ 725
Air Canada
10 Oct
ORD3:45 p.m.Chicago O'Hare Intl
8h 02m
1 stop
YWG11:47 p.m.Winnipeg
17 Oct
YWG2:05 p.m.Winnipeg
5h 43m
1 stop
ORD7:48 p.m.Chicago O'Hare Intl
C$ 726

WestJet flights from Chicago O'Hare Intl Airport to Winnipeg

Our best WestJet deals on Chicago O'Hare Intl Airport to Winnipeg flight tickets
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$ 453
WestJet
2 Oct
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
4 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 456
WestJet
5 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$ 470

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Winnipeg that are best for you.

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Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

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$ 453

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

Sun 4/10

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

1 stop9h 40m

C$ 456

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 5/10

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$ 470

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 15/10

8:04 a.m.-12:55 a.m.

2 stops16h 51m

Winnipeg

Mon 19/10

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

1 stop9h 40m

C$ 500

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 15/10

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

1 stop7h 25m

Winnipeg

Wed 21/10

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

1 stop21h 30m

C$ 511

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 23/10

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

1 stop7h 25m

Winnipeg

Mon 26/10

9:35 p.m.-12:51 p.m.

2 stops15h 16m

C$ 528

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 23/10

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

1 stop7h 25m

Winnipeg

Fri 30/10

7:00 a.m.-2:20 p.m.

1 stop7h 20m

C$ 532
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

Fri 2/10

9:20 a.m.-4:18 p.m.

1 stop6h 58m

C$ 535

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 22/10

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

1 stop7h 25m

Winnipeg

Thu 29/10

7:00 a.m.-2:20 p.m.

1 stop7h 20m

C$ 538

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 1/10

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

1 stop7h 25m

Winnipeg

Fri 2/10

9:20 a.m.-4:18 p.m.

1 stop6h 58m

C$ 542

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 O'Hare Intl Airport 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 O'Hare Intl Airport and Winnipeg?

Prices are currently typical for flights on this route.

Typical prices usually range from C$ 353 to C$ 1,592.
The lowest price recently found on this route was C$ 453.

What is the cheapest month to fly to Winnipeg?

The cheapest month to fly to Winnipeg from Chicago O'Hare Intl Airport is in March. Flight prices, which tend to average around C$ 0, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of March, then departing from Chicago O'Hare Intl Airport during the month January is also very affordable. Most momondo users find prices during this month for around C$ 0.

What is the cheapest Chicago O'Hare Intl to Winnipeg flight route?

Fly from Chicago O'Hare Intl to Winnipeg for the best Chicago O'Hare Intl - Winnipeg flight prices

What cabin class options are available on Chicago O'Hare Intl Airport to Winnipeg flights?

There are 2 cabin classes available to choose from on Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Winnipeg flights?

You could potentially save up to 23% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Winnipeg flight.

How have Chicago O'Hare Intl Airport to Winnipeg flight prices changed over time?

As of September 2026, prices for Chicago O'Hare Intl Airport to Winnipeg flights are approximately 68% cheaper when compared to flights at the same time last year.

When to book flights from Chicago O'Hare Intl Airport to Winnipeg

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport to Winnipeg according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to Winnipeg (ORD to YWG) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Winnipeg

Best price found

C$ 218

Fastest flight time

2h 37m

Direct flights

Every day

Airports in Winnipeg

1 airport
The best one-way flight to Winnipeg from Chicago O'Hare Intl Airport in the past 72 hours is C$ 218. The best round-trip flight deal from Chicago O'Hare Intl Airport to Winnipeg found on momondo in the last 72 hours is C$ 453.
The fastest flight from Chicago O'Hare Intl Airport to Winnipeg takes 2h 37m
Direct flights go from Chicago O'Hare Intl Airport to Winnipeg every day.
There is 1 airport in Winnipeg. From Chicago O'Hare Intl Airport there are direct flights to Winnipeg (YWG).
Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Winnipeg

  • How far is Chicago O'Hare Intl to Winnipeg by plane?

    Chicago O'Hare Intl and Winnipeg are 1130.2 km apart from one another. Typically, this will take 2h 37m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Winnipeg Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Winnipeg Airport were last updated today.

  • How old do you have to be to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport 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?

Finding the right flight to Winnipeg from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Winnipeg quick and easy, saving you time and money.

Can I find flights from Chicago to Winnipeg with flexible booking policies on momondo?

All flight searches from Chicago to Winnipeg on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Winnipeg?

momondo provides multiple filters to help you find the best flight to Winnipeg from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Winnipeg right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Winnipeg flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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