Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 153

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 18/5. 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

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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$ 328WestJet
Fri, 15 May - Tue, 19 May
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:05 p.m. - 6:40 p.m.
YWG
-
ORD
21h 35m
2 stops
C$ 405Multiple Airlines
Fri, 15 May - Tue, 19 May
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$ 420WestJet
Fri, 5 Jun - Sun, 7 Jun
WestJet Logo
5:30 p.m. - 12:15 p.m.
ORD
-
YWG
18h 45m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 446WestJet
Mon, 11 May - Mon, 1 Jun
WestJet Logo
2:20 p.m. - 12:40 a.m.
ORD
-
YWG
10h 20m
1 stop
WestJet Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m
1 stop
C$ 448WestJet
Fri, 13 Mar - Fri, 20 Mar
WestJet Logo
5:30 p.m. - 3:25 p.m.
ORD
-
YWG
21h 55m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 450WestJet
Mon, 11 May - Mon, 1 Jun
WestJet Logo
5:30 p.m. - 9:20 a.m.
ORD
-
YWG
15h 50m
2 stops
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
2 stops
C$ 455WestJet
Fri, 15 May - Tue, 19 May
WestJet Logo
2:20 p.m. - 11:47 p.m.
ORD
-
YWG
9h 27m
2 stops
WestJet Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m
1 stop
C$ 457WestJet
Fri, 13 Mar - Fri, 20 Mar
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$ 458WestJet
Fri, 5 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$ 463WestJet
Fri, 5 Jun - Sun, 7 Jun

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
31 May
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
5 Jun
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 327
WestJet
15 May
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
19 May
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 328
WestJet
5 Jun
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
7 Jun
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 420

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
22 Feb
ORD9:15 a.m.Chicago O'Hare Intl
2h 42m
YWG11:57 a.m.Winnipeg
26 Feb
YWG5:30 a.m.Winnipeg
17h 30m
2 stops
ORD11:00 p.m.Chicago O'Hare Intl
C$ 1,147
United Airlines
22 Feb
ORD9:15 a.m.Chicago O'Hare Intl
2h 42m
YWG11:57 a.m.Winnipeg
25 Feb
YWG5:30 a.m.Winnipeg
17h 30m
2 stops
ORD11:00 p.m.Chicago O'Hare Intl
C$ 1,163
United Airlines
19 Feb
ORD9:15 a.m.Chicago O'Hare Intl
2h 42m
YWG11:57 a.m.Winnipeg
23 Feb
YWG2:20 p.m.Winnipeg
2h 25m
ORD4:45 p.m.Chicago O'Hare Intl
C$ 1,199

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 9 February 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

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 15/5

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

1 stop7h 25m

Winnipeg

Tue 19/5

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

1 stop9h 40m

C$ 328

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 15/5

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

1 stop7h 25m

Winnipeg

Tue 19/5

9:05 p.m.-6:40 p.m.

2 stops21h 35m

C$ 405

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

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

1 stop7h 25m

Winnipeg

Sun 7/6

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

1 stop9h 40m

C$ 420

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 11/5

5:30 p.m.-12:15 p.m.

1 stop18h 45m

Winnipeg

Mon 1/6

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

1 stop9h 40m

C$ 446

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 13/3

2:20 p.m.-12:40 a.m.

1 stop10h 20m

Winnipeg

Fri 20/3

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

1 stop7h 20m

C$ 448

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 11/5

5:30 p.m.-3:25 p.m.

1 stop21h 55m

Winnipeg

Mon 1/6

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

1 stop9h 40m

C$ 450

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 15/5

5:30 p.m.-9:20 a.m.

2 stops15h 50m

Winnipeg

Tue 19/5

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

2 stops9h 40m

C$ 455

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 13/3

2:20 p.m.-11:47 p.m.

2 stops9h 27m

Winnipeg

Fri 20/3

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

1 stop7h 20m

C$ 457

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

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

1 stop7h 25m

Winnipeg

Sun 7/6

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

1 stop9h 40m

C$ 458

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

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

1 stop7h 25m

Winnipeg

Sun 7/6

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

1 stop9h 40m

C$ 463

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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$ 438. Be sure to avoid booking your departure on a Wednesday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Wednesday is C$ 871.

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$ 438. 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$ 919. 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 53% 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 February 2026, prices for Chicago O'Hare Intl Airport to Winnipeg flights are approximately 63% 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

Fastest flight time

2h 24m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

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 on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport in Winnipeg. From Chicago O'Hare Intl Airport there are direct flights to 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 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.

An easier way to manage your Winnipeg trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 11/3
Wed 18/3
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada