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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 252

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 13/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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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.
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 451WestJet
Thu, 1 Oct - Sun, 11 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
4:55 p.m. - 4:40 p.m.
YWG
-
ORD
23h 45m
1 stop
C$ 502WestJet
Thu, 1 Oct - Sat, 10 Oct
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:20 a.m. - 4:18 p.m.
YWG
-
ORD
6h 58m
1 stop
C$ 513Multiple Airlines
Fri, 12 Jun - Wed, 17 Jun
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 520WestJet
Thu, 27 Aug - Mon, 31 Aug
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
9:05 p.m. - 4:40 p.m.
YWG
-
ORD
19h 35m
1 stop
C$ 556WestJet
Thu, 4 Jun - Sun, 7 Jun
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 557WestJet
Thu, 15 Oct - Mon, 19 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 558WestJet
Sun, 2 Aug - Wed, 12 Aug
Multiple Airlines Logo
7:00 a.m. - 5:58 p.m.
ORD
-
YWG
10h 58m
2 stops
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 569Multiple Airlines
Thu, 1 Oct - Sun, 11 Oct
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
4:55 p.m. - 5:42 a.m.
YWG
-
ORD
12h 47m
2 stops
C$ 579Multiple Airlines
Thu, 1 Oct - Sat, 10 Oct
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
12:15 p.m. - 7:29 p.m.
YWG
-
ORD
7h 14m
1 stop
C$ 583Multiple Airlines
Mon, 6 Jul - Fri, 17 Jul

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
1 Oct
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
11 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 451
WestJet
1 Oct
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
10 Oct
YWG4:55 p.m.Winnipeg
23h 45m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 502
WestJet
27 Aug
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
31 Aug
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 520

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
28 May
ORD11:40 a.m.Chicago O'Hare Intl
8h 09m
1 stop
YWG7:49 p.m.Winnipeg
31 May
YWG9:20 a.m.Winnipeg
7h 00m
1 stop
ORD4:20 p.m.Chicago O'Hare Intl
C$ 948
Porter Airlines
29 May
ORD9:42 a.m.Chicago O'Hare Intl
10h 07m
1 stop
YWG7:49 p.m.Winnipeg
31 May
YWG9:20 a.m.Winnipeg
7h 00m
1 stop
ORD4:20 p.m.Chicago O'Hare Intl
C$ 1,077
Porter Airlines
27 May
ORD11:40 a.m.Chicago O'Hare Intl
7h 54m
1 stop
YWG7:34 p.m.Winnipeg
2 Jun
YWG9:20 a.m.Winnipeg
27h 25m
1 stop
ORD12:45 p.m.Chicago O'Hare Intl
C$ 1,169

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 21 May 2026.
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

Cheapest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/10

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

1 stop7h 25m

Winnipeg

Sun 11/10

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

1 stop9h 40m

C$ 451

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/10

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

1 stop7h 25m

Winnipeg

Sat 10/10

4:55 p.m.-4:40 p.m.

1 stop23h 45m

C$ 502
Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 12/6

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

1 stop7h 25m

Winnipeg

Wed 17/6

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

1 stop6h 58m

C$ 513

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 27/8

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

1 stop7h 25m

Winnipeg

Mon 31/8

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

1 stop9h 40m

C$ 520

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 4/6

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

1 stop7h 25m

Winnipeg

Sun 7/6

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

1 stop19h 35m

C$ 556

ChicagoWinnipeg

ORD - YWG

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$ 557

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 2/8

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

1 stop7h 25m

Winnipeg

Wed 12/8

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

1 stop9h 40m

C$ 558

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/10

7:00 a.m.-5:58 p.m.

2 stops10h 58m

Winnipeg

Sun 11/10

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

1 stop9h 40m

C$ 569

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/10

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

1 stop7h 25m

Winnipeg

Sat 10/10

4:55 p.m.-5:42 a.m.

2 stops12h 47m

C$ 579

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 6/7

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

1 stop7h 25m

Winnipeg

Fri 17/7

12:15 p.m.-7:29 p.m.

1 stop7h 14m

C$ 583

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?

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 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$ 432. 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$ 924. 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 Airport to Winnipeg flights?

There is only 1 cabin class 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 48% 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 May 2026, prices for Chicago O'Hare Intl Airport to Winnipeg flights are approximately 46% 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

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 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 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
Morden
Selkirk
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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