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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 105

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 O'Hare Intl Airport to Winnipeg departing on 27/11. 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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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
1:24 p.m. - 3:07 p.m.ORD-YWG
25h 43m1 stop
Multiple Airlines Logo
4:55 p.m. - 7:43 p.m.YWG-ORD
26h 48m1 stop
C$ 304Multiple Airlines
Find Deal
Sat, 13 Dec - Sun, 11 Jan
Multiple Airlines Logo
5:05 a.m. - 12:41 a.m.ORD-YWG
19h 36m2 stops
Multiple Airlines Logo
7:30 a.m. - 10:24 p.m.YWG-ORD
14h 54m1 stop
C$ 318Multiple Airlines
Find Deal
Thu, 4 Dec - Sun, 7 Dec
Multiple Airlines Logo
10:00 a.m. - 12:41 a.m.ORD-YWG
14h 41m2 stops
Multiple Airlines Logo
7:30 a.m. - 10:24 p.m.YWG-ORD
14h 54m1 stop
C$ 320Multiple Airlines
Find Deal
Tue, 9 Dec - Fri, 12 Dec
Multiple Airlines Logo
4:22 p.m. - 3:07 p.m.ORD-YWG
22h 45m1 stop
Multiple Airlines Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
C$ 332Multiple Airlines
Find Deal
Tue, 9 Dec - Fri, 12 Dec
Multiple Airlines Logo
1:24 p.m. - 3:07 p.m.ORD-YWG
25h 43m1 stop
Multiple Airlines Logo
7:30 a.m. - 9:54 p.m.YWG-ORD
14h 24m2 stops
C$ 352Multiple Airlines
Find Deal
Sat, 13 Dec - Sun, 11 Jan
Multiple Airlines Logo
6:35 p.m. - 3:07 p.m.ORD-YWG
20h 32m1 stop
Multiple Airlines Logo
7:30 a.m. - 11:34 a.m.YWG-ORD
28h 04m1 stop
C$ 369Multiple Airlines
Find Deal
Sat, 22 Nov - Wed, 26 Nov
Multiple Airlines Logo
7:21 p.m. - 3:07 p.m.ORD-YWG
19h 46m2 stops
Multiple Airlines Logo
7:30 a.m. - 11:34 a.m.YWG-ORD
28h 04m1 stop
C$ 376Multiple Airlines
Find Deal
Sat, 22 Nov - Wed, 26 Nov
Multiple Airlines Logo
8:48 p.m. - 12:43 a.m.ORD-YWG
27h 55m1 stop
Multiple Airlines Logo
4:10 p.m. - 9:33 p.m.YWG-ORD
29h 23m2 stops
C$ 383Multiple Airlines
Find Deal
Sat, 10 Jan - Sun, 25 Jan
WestJet Logo
2:20 p.m. - 10:41 p.m.ORD-YWG
8h 21m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 503WestJet
Find Deal
Fri, 9 Jan - Mon, 4 May
WestJet Logo
2:20 p.m. - 10:41 p.m.ORD-YWG
8h 21m1 stop
WestJet Logo
12:40 p.m. - 4:48 p.m.YWG-ORD
4h 08m1 stop
C$ 528WestJet
Find Deal
Fri, 9 Jan - Sat, 2 May

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
9 Jan
ORD2:20 p.m.Chicago O'Hare Intl
8h 21m
1 stop
YWG10:41 p.m.Winnipeg
4 May
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 503
Find similar
WestJet
9 Jan
ORD2:20 p.m.Chicago O'Hare Intl
8h 21m
1 stop
YWG10:41 p.m.Winnipeg
2 May
YWG12:40 p.m.Winnipeg
4h 08m
1 stop
ORD4:48 p.m.Chicago O'Hare Intl
C$ 528
Find similar
WestJet
29 Dec
ORD6:30 p.m.Chicago O'Hare Intl
5h 14m
1 stop
YWG11:44 p.m.Winnipeg
26 Apr
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 535
Find similar

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
12 Nov
ORD9:22 a.m.Chicago O'Hare Intl
2h 35m
YWG11:57 a.m.Winnipeg
15 Nov
YWG2:20 p.m.Winnipeg
2h 41m
ORD5:01 p.m.Chicago O'Hare Intl
C$ 1,177
Find similar
Air Canada
13 Nov
ORD3:55 p.m.Chicago O'Hare Intl
7h 59m
1 stop
YWG11:54 p.m.Winnipeg
14 Nov
YWG2:20 p.m.Winnipeg
2h 41m
ORD5:01 p.m.Chicago O'Hare Intl
C$ 1,194
Find similar
Air Canada
9 Nov
ORD8:45 a.m.Chicago O'Hare Intl
6h 58m
1 stop
YWG3:43 p.m.Winnipeg
10 Nov
YWG2:20 p.m.Winnipeg
2h 41m
ORD5:01 p.m.Chicago O'Hare Intl
C$ 1,461
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 30 October 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 13/12

1:24 p.m.-3:07 p.m.

1 stop25h 43m

Winnipeg

Sun 11/1

4:55 p.m.-7:43 p.m.

1 stop26h 48m

C$ 304

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 4/12

5:05 a.m.-12:41 a.m.

2 stops19h 36m

Winnipeg

Sun 7/12

7:30 a.m.-10:24 p.m.

1 stop14h 54m

C$ 318

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 9/12

10:00 a.m.-12:41 a.m.

2 stops14h 41m

Winnipeg

Fri 12/12

7:30 a.m.-10:24 p.m.

1 stop14h 54m

C$ 320

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 9/12

4:22 p.m.-3:07 p.m.

1 stop22h 45m

Winnipeg

Fri 12/12

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

1 stop7h 20m

C$ 332

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 13/12

1:24 p.m.-3:07 p.m.

1 stop25h 43m

Winnipeg

Sun 11/1

7:30 a.m.-9:54 p.m.

2 stops14h 24m

C$ 352

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 22/11

6:35 p.m.-3:07 p.m.

1 stop20h 32m

Winnipeg

Wed 26/11

7:30 a.m.-11:34 a.m.

1 stop28h 04m

C$ 369

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 22/11

7:21 p.m.-3:07 p.m.

2 stops19h 46m

Winnipeg

Wed 26/11

7:30 a.m.-11:34 a.m.

1 stop28h 04m

C$ 376

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 10/1

8:48 p.m.-12:43 a.m.

1 stop27h 55m

Winnipeg

Sun 25/1

4:10 p.m.-9:33 p.m.

2 stops29h 23m

C$ 383

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/1

2:20 p.m.-10:41 p.m.

1 stop8h 21m

Winnipeg

Mon 4/5

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 503

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/1

2:20 p.m.-10:41 p.m.

1 stop8h 21m

Winnipeg

Sat 2/5

12:40 p.m.-4:48 p.m.

1 stop4h 08m

C$ 528

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 May. Flight prices, which tend to average around C$ 321, 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 O'Hare Intl Airport during the month April is also very affordable. Most momondo users find prices during this month for around C$ 366.

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$ 447. 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$ 1,013.

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 O'Hare Intl Airport to Winnipeg when you can find flight prices for as low as C$ 447. 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$ 939. 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 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 to Winnipeg flights?

There is only 1 cabin class available to choose from on Chicago O'Hare Intl 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 79% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Winnipeg flight.

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

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Winnipeg

1 airport
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 near Winnipeg: Winnipeg (YWG)
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  • 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 5h 14m 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
Selkirk
Morden
Portage la Prairie

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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