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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 141

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 6/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Winnipeg

Cheap round-trip flights

WestJet Logo
5:30 p.m. - 9:01 a.m.ORD-YWG
15h 31m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 288WestJet
Find Deal
Mon, 6 Oct - Sun, 12 Oct
WestJet Logo
5:30 p.m. - 11:10 p.m.ORD-YWG
29h 40m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 292WestJet
Find Deal
Thu, 9 Oct - Sun, 12 Oct
WestJet Logo
5:30 p.m. - 11:26 a.m.ORD-YWG
17h 56m2 stops
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 296WestJet
Find Deal
Mon, 6 Oct - Fri, 17 Oct
WestJet Logo
5:30 p.m. - 11:41 a.m.ORD-YWG
18h 11m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 298WestJet
Find Deal
Fri, 10 Oct - Sun, 12 Oct
WestJet Logo
5:30 p.m. - 11:26 a.m.ORD-YWG
17h 56m2 stops
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 299WestJet
Find Deal
Sat, 11 Oct - Fri, 17 Oct
WestJet Logo
5:30 p.m. - 9:01 a.m.ORD-YWG
15h 31m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 302WestJet
Find Deal
Sun, 12 Oct - Fri, 17 Oct
WestJet Logo
5:30 p.m. - 8:00 a.m.ORD-YWG
14h 30m2 stops
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 320WestJet
Find Deal
Sun, 12 Oct - Fri, 17 Oct
WestJet Logo
5:30 p.m. - 11:41 a.m.ORD-YWG
18h 11m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 321WestJet
Find Deal
Thu, 16 Oct - Fri, 24 Oct
Logo
5:30 p.m. - 11:26 a.m.ORD-YWG
17h 56m2 stops
Logo
9:00 a.m. - 11:44 p.m.YWG-ORD
14h 44m1 stop
C$ 323
Find Deal
Mon, 6 Oct - Mon, 13 Oct
Logo
3:12 p.m. - 4:22 p.m.ORD-YWG
25h 10m1 stop
Logo
9:00 a.m. - 11:44 p.m.YWG-ORD
14h 44m1 stop
C$ 324
Find Deal
Wed, 8 Oct - Mon, 13 Oct

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
6 Oct
ORD5:30 p.m.Chicago O'Hare Intl
15h 31m
1 stop
YWG9:01 a.m.Winnipeg
12 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 288
Find similar
WestJet
9 Oct
ORD5:30 p.m.Chicago O'Hare Intl
29h 40m
1 stop
YWG11:10 p.m.Winnipeg
12 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 292
Find similar
WestJet
6 Oct
ORD5:30 p.m.Chicago O'Hare Intl
17h 56m
2 stops
YWG11:26 a.m.Winnipeg
17 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 296
Find similar

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

Our best United Airlines deals on Chicago O'Hare Intl Airport to Winnipeg flight tickets
United Airlines
25 Sep
ORD7:54 p.m.Chicago O'Hare Intl
2h 39m
YWG10:33 p.m.Winnipeg
29 Sep
YWG7:00 a.m.Winnipeg
2h 31m
ORD9:31 a.m.Chicago O'Hare Intl
C$ 1,138
Find similar
United Airlines
25 Sep
ORD7:10 a.m.Chicago O'Hare Intl
5h 59m
1 stop
YWG1:09 p.m.Winnipeg
30 Sep
YWG2:20 p.m.Winnipeg
2h 31m
ORD4:51 p.m.Chicago O'Hare Intl
C$ 1,150
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 15 September 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

Mon 6/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

Winnipeg

Sun 12/10

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

1 stop8h 13m

C$ 288

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 9/10

5:30 p.m.-11:10 p.m.

1 stop29h 40m

Winnipeg

Sun 12/10

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

1 stop8h 13m

C$ 292

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 6/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

Winnipeg

Fri 17/10

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

1 stop8h 13m

C$ 296

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/10

5:30 p.m.-11:41 a.m.

1 stop18h 11m

Winnipeg

Sun 12/10

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

1 stop8h 13m

C$ 298

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 11/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

Winnipeg

Fri 17/10

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

1 stop8h 13m

C$ 299

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 12/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

Winnipeg

Fri 17/10

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

1 stop8h 13m

C$ 302

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 12/10

5:30 p.m.-8:00 a.m.

2 stops14h 30m

Winnipeg

Fri 17/10

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

1 stop8h 13m

C$ 320

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 16/10

5:30 p.m.-11:41 a.m.

1 stop18h 11m

Winnipeg

Fri 24/10

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

1 stop8h 13m

C$ 321

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 6/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

Winnipeg

Mon 13/10

9:00 a.m.-11:44 p.m.

1 stop14h 44m

C$ 322

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 8/10

3:12 p.m.-4:22 p.m.

1 stop25h 10m

Winnipeg

Mon 13/10

9:00 a.m.-11:44 p.m.

1 stop14h 44m

C$ 324

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 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$ 318, 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$ 363.

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$ 443. 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$ 1,004.

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$ 444. 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$ 930. 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 47% 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 30m

Direct flights

Every day

Airports in Winnipeg

1 airport
The fastest flight from Chicago O'Hare Intl Airport to Winnipeg takes 2h 30m
Direct flights go from Chicago O'Hare Intl Airport to Winnipeg every day.
There is 1 airport near Winnipeg: Winnipeg (YWG)
Search flight deals

  • 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 7h 45m 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 many operators does momondo search for flights from Chicago O'Hare Intl Airport to Winnipeg Airport?

  • 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?

  • What is the most popular airline from Chicago O'Hare Intl Airport to Winnipeg?

Best airlines flying from Chicago O'Hare Intl Airport to Winnipeg

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Winnipeg with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 443Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

  • Air Canada Flights From Chicago O'Hare Intl Airport to Winnipeg

    Air Canada is one of the most popular airlines flying from Chicago O'Hare Intl Airport to Winnipeg, operating 14 flights/week on average for this route. A good Air Canada flight deal for Chicago O'Hare Intl Airport to Winnipeg starts from C$ 320 round-trip, up to an average price of C$ 725. Our users have rated Air Canada at 7.1/10.

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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