Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 265

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.
Multiple Airlines Logo
10:05 a.m. - 7:10 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
8h 05m1 stop Toronto Pearson Intl
Multiple Airlines Logo
11:00 a.m. - 7:58 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 58m1 stop Toronto Pearson Intl
C$ 614Multiple Airlines
Fri, 4 Dec - Sun, 6 Dec
Multiple Airlines Logo
10:29 p.m. - 5:25 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
17h 56m2 stops Atlanta Hartsfield-Jackson Calgary
Multiple Airlines Logo
7:00 a.m. - 12:00 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
30h 00m1 stop Atlanta Hartsfield-Jackson
C$ 626Multiple Airlines
Mon, 14 Dec - Mon, 21 Dec
Multiple Airlines Logo
10:29 p.m. - 5:25 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
17h 56m2 stops Atlanta Hartsfield-Jackson Calgary
Multiple Airlines Logo
7:00 a.m. - 12:00 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
30h 00m1 stop Atlanta Hartsfield-Jackson
C$ 633Multiple Airlines
Mon, 14 Dec - Mon, 21 Dec
Multiple Airlines Logo
5:58 a.m. - 2:40 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 42m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
9:35 p.m. - 11:50 a.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
15h 15m2 stops Calgary Atlanta Hartsfield-Jackson
C$ 648Multiple Airlines
Mon, 21 Dec - Thu, 28 Jan
Multiple Airlines Logo
6:00 a.m. - 2:40 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 40m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
11:40 a.m. - 11:30 a.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
24h 50m2 stops Ottawa Toronto Island
C$ 655Multiple Airlines
Fri, 5 Feb - Tue, 9 Feb
Multiple Airlines Logo
6:00 a.m. - 2:40 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 40m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:40 p.m. - 11:30 a.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
23h 50m2 stops Ottawa Toronto Island
C$ 658Multiple Airlines
Fri, 5 Feb - Sun, 7 Feb
Multiple Airlines Logo
5:58 a.m. - 2:40 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 42m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
7:00 a.m. - 11:50 a.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
29h 50m1 stop Atlanta Hartsfield-Jackson
C$ 659Multiple Airlines
Fri, 18 Dec - Mon, 11 Jan
Multiple Airlines Logo
5:58 a.m. - 2:40 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 42m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:54 a.m. - 5:30 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
11h 36m1 stop Toronto Pearson Intl
C$ 690Multiple Airlines
Mon, 21 Dec - Thu, 28 Jan
Multiple Airlines Logo
5:58 a.m. - 2:40 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 42m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
11:00 a.m. - 4:14 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
54h 14m2 stops Toronto Pearson Intl Fort Lauderdale
C$ 690Multiple Airlines
Fri, 18 Dec - Mon, 11 Jan
Multiple Airlines Logo
12:15 p.m. - 1:44 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
12h 29m1 stop Toronto Island
Multiple Airlines Logo
9:35 p.m. - 11:34 a.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
14h 59m2 stops Calgary Toronto Pearson Intl
C$ 698Multiple Airlines
Fri, 4 Dec - Sun, 6 Dec

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Porter Airlines flights from Chicago O'Hare Intl Airport to Winnipeg

Our best Porter Airlines deals on Chicago O'Hare Intl Airport to Winnipeg flight tickets
Porter Airlines
12 Mar
ORD12:20 p.m.Chicago O'Hare Intl
29h 59m
2 stops
YWG7:19 p.m.Winnipeg
20 Mar
YWG7:00 a.m.Winnipeg
7h 31m
1 stop
ORD2:31 p.m.Chicago O'Hare Intl
C$ 880
Porter Airlines
11 Nov
ORD12:15 p.m.Chicago O'Hare Intl
29h 51m
2 stops
YWG7:06 p.m.Winnipeg
16 Nov
YWG7:00 a.m.Winnipeg
7h 01m
1 stop
ORD1:01 p.m.Chicago O'Hare Intl
C$ 944
Porter Airlines
11 Nov
ORD6:20 p.m.Chicago O'Hare Intl
23h 46m
2 stops
YWG7:06 p.m.Winnipeg
16 Nov
YWG7:00 a.m.Winnipeg
7h 01m
1 stop
ORD1:01 p.m.Chicago O'Hare Intl
C$ 1,007

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
11 Nov
ORD4:30 p.m.Chicago O'Hare Intl
7h 14m
1 stop
YWG12:44 a.m.Winnipeg
19 Nov
YWG9:15 a.m.Winnipeg
11h 43m
1 stop
ORD7:58 p.m.Chicago O'Hare Intl
C$ 906
Air Canada
11 Nov
ORD9:35 a.m.Chicago O'Hare Intl
2h 48m
YWG1:23 p.m.Winnipeg
19 Nov
YWG6:15 a.m.Winnipeg
7h 58m
1 stop
ORD1:13 p.m.Chicago O'Hare Intl
C$ 1,290

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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Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 4/12

10:05 a.m.-7:10 p.m.

1 stop8h 05m

Winnipeg

Sun 6/12

11:00 a.m.-7:58 p.m.

1 stop9h 58m

C$ 614

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 14/12

10:29 p.m.-5:25 p.m.

2 stops17h 56m

Winnipeg

Mon 21/12

7:00 a.m.-12:00 p.m.

1 stop30h 00m

C$ 626

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 14/12

10:29 p.m.-5:25 p.m.

2 stops17h 56m

Winnipeg

Mon 21/12

7:00 a.m.-12:00 p.m.

1 stop30h 00m

C$ 633

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 21/12

5:58 a.m.-2:40 p.m.

1 stop7h 42m

Winnipeg

Thu 28/1

9:35 p.m.-11:50 a.m.

2 stops15h 15m

C$ 648

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 5/2

6:00 a.m.-2:40 p.m.

1 stop7h 40m

Winnipeg

Tue 9/2

11:40 a.m.-11:30 a.m.

2 stops24h 50m

C$ 655

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 5/2

6:00 a.m.-2:40 p.m.

1 stop7h 40m

Winnipeg

Sun 7/2

12:40 p.m.-11:30 a.m.

2 stops23h 50m

C$ 658

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 18/12

5:58 a.m.-2:40 p.m.

1 stop7h 42m

Winnipeg

Mon 11/1

7:00 a.m.-11:50 a.m.

1 stop29h 50m

C$ 659

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 21/12

5:58 a.m.-2:40 p.m.

1 stop7h 42m

Winnipeg

Thu 28/1

6:54 a.m.-5:30 p.m.

1 stop11h 36m

C$ 690

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 18/12

5:58 a.m.-2:40 p.m.

1 stop7h 42m

Winnipeg

Mon 11/1

11:00 a.m.-4:14 p.m.

2 stops54h 14m

C$ 690

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 4/12

12:15 p.m.-1:44 a.m.

1 stop12h 29m

Winnipeg

Sun 6/12

9:35 p.m.-11:34 a.m.

2 stops14h 59m

C$ 698

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 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 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?

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Winnipeg.

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

As of October 2026, prices for Chicago O'Hare Intl Airport to Winnipeg flights are approximately 5% more expensive 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$ 265

Fastest flight time

2h 24m

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$ 265. The best round-trip flight deal from Chicago O'Hare Intl Airport to Winnipeg found on momondo in the last 72 hours is C$ 614.
The fastest flight from Chicago O'Hare Intl Airport to Winnipeg takes 2h 24m
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).

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 24m 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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