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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 209

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 25/8. 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
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
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 442WestJet
Thu, 1 Oct - Sun, 4 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$ 445WestJet
Thu, 1 Oct - Sun, 4 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$ 448WestJet
Thu, 1 Oct - Sun, 4 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$ 462WestJet
Fri, 25 Sep - Sun, 4 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$ 463WestJet
Sun, 27 Sep - Sun, 4 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$ 465WestJet
Sun, 27 Sep - Sun, 4 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$ 466WestJet
Fri, 25 Sep - Thu, 1 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$ 468WestJet
Sun, 27 Sep - Thu, 1 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$ 476WestJet
Fri, 25 Sep - Tue, 29 Sep
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$ 478WestJet
Thu, 10 Sep - Mon, 14 Sep

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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
10 Nov
ORD11:45 a.m.Chicago O'Hare Intl
10h 12m
1 stop
YWG9:57 p.m.Winnipeg
22 Nov
YWG7:00 a.m.Winnipeg
10h 30m
1 stop
ORD5:30 p.m.Chicago O'Hare Intl
C$ 509
Porter Airlines
8 Jul
ORD9:45 a.m.Chicago O'Hare Intl
9h 49m
1 stop
YWG7:34 p.m.Winnipeg
14 Jul
YWG12:15 p.m.Winnipeg
7h 14m
1 stop
ORD7:29 p.m.Chicago O'Hare Intl
C$ 1,274
Porter Airlines
8 Jul
ORD9:45 a.m.Chicago O'Hare Intl
9h 49m
1 stop
YWG7:34 p.m.Winnipeg
14 Jul
YWG12:15 p.m.Winnipeg
7h 14m
1 stop
ORD7:29 p.m.Chicago O'Hare Intl
C$ 1,295

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
4 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 442
WestJet
1 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$ 445
WestJet
1 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$ 448

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 7 July 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
Quickest 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 4/10

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

1 stop9h 40m

C$ 442

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/10

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$ 445

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/10

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$ 448

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 25/9

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$ 462

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 27/9

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$ 463

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 27/9

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$ 465

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 25/9

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

1 stop7h 25m

Winnipeg

Thu 1/10

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

1 stop9h 40m

C$ 466

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 27/9

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

1 stop7h 25m

Winnipeg

Thu 1/10

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

1 stop9h 40m

C$ 468

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 25/9

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

1 stop7h 25m

Winnipeg

Tue 29/9

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

1 stop9h 40m

C$ 476

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/9

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

1 stop7h 25m

Winnipeg

Mon 14/9

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

1 stop9h 40m

C$ 478

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 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 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 18% 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 July 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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