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Cheap flights from Winnipeg to Chicago from C$ 182

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Chicago departing on 26/11. 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 Winnipeg to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:30 a.m. - 11:54 a.m.YWG-ORD
28h 24m1 stop
Multiple Airlines Logo
10:24 a.m. - 12:41 a.m.ORD-YWG
14h 17m2 stops
C$ 276Multiple Airlines
Find Deal
Fri, 5 Dec - Sun, 7 Dec
Multiple Airlines Logo
7:30 a.m. - 11:54 a.m.YWG-ORD
28h 24m1 stop
Multiple Airlines Logo
6:11 a.m. - 3:07 p.m.ORD-YWG
8h 56m1 stop
C$ 282Multiple Airlines
Find Deal
Fri, 5 Dec - Sun, 7 Dec
Multiple Airlines Logo
7:30 a.m. - 12:08 a.m.YWG-ORD
16h 38m1 stop
Multiple Airlines Logo
8:00 a.m. - 12:41 a.m.ORD-YWG
16h 41m2 stops
C$ 297Multiple Airlines
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Multiple Airlines Logo
9:00 p.m. - 11:14 a.m.YWG-ORD
14h 14m2 stops
Multiple Airlines Logo
12:37 p.m. - 3:07 p.m.ORD-YWG
26h 30m1 stop
C$ 300Multiple Airlines
Find Deal
Tue, 11 Nov - Tue, 18 Nov
Multiple Airlines Logo
9:00 p.m. - 2:40 p.m.YWG-ORD
17h 40m2 stops
Multiple Airlines Logo
6:11 a.m. - 3:07 p.m.ORD-YWG
8h 56m1 stop
C$ 341Multiple Airlines
Find Deal
Thu, 4 Dec - Sun, 7 Dec
Multiple Airlines Logo
7:30 a.m. - 11:54 a.m.YWG-ORD
28h 24m1 stop
Multiple Airlines Logo
9:27 p.m. - 12:39 a.m.ORD-YWG
27h 12m2 stops
C$ 351Multiple Airlines
Find Deal
Fri, 5 Dec - Mon, 8 Dec
Multiple Airlines Logo
7:30 a.m. - 11:54 a.m.YWG-ORD
28h 24m1 stop
Multiple Airlines Logo
9:27 p.m. - 12:39 a.m.ORD-YWG
27h 12m2 stops
C$ 353Multiple Airlines
Find Deal
Fri, 5 Dec - Mon, 8 Dec
Multiple Airlines Logo
7:30 a.m. - 11:54 a.m.YWG-ORD
28h 24m1 stop
Multiple Airlines Logo
7:10 a.m. - 6:03 p.m.ORD-YWG
10h 53m1 stop
C$ 364Multiple Airlines
Find Deal
Fri, 5 Dec - Mon, 8 Dec
WestJet Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
WestJet Logo
2:20 p.m. - 1:52 p.m.ORD-YWG
23h 32m2 stops
C$ 451WestJet
Find Deal
Fri, 5 Dec - Mon, 8 Dec
WestJet Logo
7:30 a.m. - 6:43 p.m.YWG-ORD
11h 13m1 stop
WestJet Logo
2:20 p.m. - 10:41 p.m.ORD-YWG
8h 21m1 stop
C$ 531WestJet
Find Deal
Fri, 5 Dec - Mon, 8 Dec

WestJet flights from Winnipeg to Chicago O'Hare Intl Airport

Our best WestJet deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
WestJet
5 Dec
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
8 Dec
ORD2:20 p.m.Chicago O'Hare Intl
23h 32m
2 stops
YWG1:52 p.m.Winnipeg
C$ 451
Find similar
WestJet
5 Dec
YWG7:30 a.m.Winnipeg
11h 13m
1 stop
ORD6:43 p.m.Chicago O'Hare Intl
8 Dec
ORD2:20 p.m.Chicago O'Hare Intl
8h 21m
1 stop
YWG10:41 p.m.Winnipeg
C$ 531
Find similar
WestJet
25 Apr
YWG6:55 p.m.Winnipeg
21h 48m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
18h 10m
1 stop
YWG11:40 a.m.Winnipeg
C$ 563
Find similar

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

Our best Porter Airlines deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Porter Airlines
6 Nov
YWG6:00 a.m.Winnipeg
6h 27m
1 stop
ORD12:27 p.m.Chicago O'Hare Intl
8 Nov
ORD8:03 a.m.Chicago O'Hare Intl
7h 27m
1 stop
YWG3:30 p.m.Winnipeg
C$ 1,177
Find similar
Porter Airlines
8 Nov
YWG6:00 a.m.Winnipeg
8h 11m
1 stop
ORD2:11 p.m.Chicago O'Hare Intl
15 Nov
ORD8:03 a.m.Chicago O'Hare Intl
7h 27m
1 stop
YWG3:30 p.m.Winnipeg
C$ 1,204
Find similar
Porter Airlines
6 Nov
YWG6:00 a.m.Winnipeg
6h 27m
1 stop
ORD12:27 p.m.Chicago O'Hare Intl
6 Nov
ORD3:00 p.m.Chicago O'Hare Intl
24h 30m
1 stop
YWG3:30 p.m.Winnipeg
C$ 1,255
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Chicago O'Hare Intl Airport 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 Winnipeg to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Sun 7/12

10:24 a.m.-12:41 a.m.

2 stops14h 17m

C$ 276

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Sun 7/12

6:11 a.m.-3:07 p.m.

1 stop8h 56m

C$ 282

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 26/11

7:30 a.m.-12:08 a.m.

1 stop16h 38m

Chicago O'Hare Intl

Wed 3/12

8:00 a.m.-12:41 a.m.

2 stops16h 41m

C$ 297

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 11/11

9:00 p.m.-11:14 a.m.

2 stops14h 14m

Chicago O'Hare Intl

Tue 18/11

12:37 p.m.-3:07 p.m.

1 stop26h 30m

C$ 300

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 4/12

9:00 p.m.-2:40 p.m.

2 stops17h 40m

Chicago O'Hare Intl

Sun 7/12

6:11 a.m.-3:07 p.m.

1 stop8h 56m

C$ 341

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Mon 8/12

9:27 p.m.-12:39 a.m.

2 stops27h 12m

C$ 350

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Mon 8/12

9:27 p.m.-12:39 a.m.

2 stops27h 12m

C$ 353

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Mon 8/12

7:10 a.m.-6:03 p.m.

1 stop10h 53m

C$ 364

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/12

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

1 stop7h 20m

Chicago O'Hare Intl

Mon 8/12

2:20 p.m.-1:52 p.m.

2 stops23h 32m

C$ 451

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/12

7:30 a.m.-6:43 p.m.

1 stop11h 13m

Chicago O'Hare Intl

Mon 8/12

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

1 stop8h 21m

C$ 531

Flights are sorted by cheapest round-trip flights first.

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See travel insights to Chicago from

How to get the cheapest flight ticket from Winnipeg to Chicago O'Hare Intl Airport

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 Winnipeg and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

In general, September is the cheapest month to fly from Winnipeg to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 493. The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around C$ 517.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as C$ 805. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago O'Hare Intl Airport for around C$ 1,003.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the evening is the cheapest time of day to fly from Winnipeg to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 710. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 969 on average. Flights to Chicago O'Hare Intl Airport from Winnipeg in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.

What is the cheapest Winnipeg to Chicago O'Hare Intl flight route?

Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Chicago O'Hare Intl flight prices

What cabin class options are available on Winnipeg to Chicago O'Hare Intl flights?

There are 3 cabin classes available to choose from on Winnipeg to Chicago O'Hare Intl 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 Winnipeg to Chicago O'Hare Intl Airport flights?

You could potentially save up to 67% on your flight if you consider stops on a Winnipeg to Chicago O'Hare Intl Airport flight.

How have Winnipeg to Chicago O'Hare Intl Airport flight prices changed over time?

As of October 2025, prices for Winnipeg to Chicago O'Hare Intl Airport flights are approximately 62% cheaper when compared to flights at the same time last year.

When to book flights from Winnipeg to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Winnipeg to Chicago O'Hare Intl Airport (YWG to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago O'Hare Intl Airport

Best price found

C$ 282

Fastest flight time

2h 21m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is C$ 282. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 613.
The fastest flight from Winnipeg to Chicago O'Hare Intl Airport takes 2h 21m
Direct flights go from Winnipeg to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is Winnipeg to Chicago O'Hare Intl by plane?

    Winnipeg and Chicago O'Hare Intl are 1130.2 km apart from one another. Flights usually cover this in 3h 47m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Winnipeg Airport to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl 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 Winnipeg to Chicago O'Hare Intl Airport?

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

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

Compare and see reviews for airlines that fly from Winnipeg to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 202Free CancellationRating
7.2
3,152 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 365Free CancellationRating
7.1
10,381 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 491Free CancellationRating
7.4
8,998 reviews
Search United Airlines flights

  • United Airlines Flights From Winnipeg to Chicago O'Hare Intl Airport

    United Airlines flies from Winnipeg to Chicago O'Hare Intl Airport around 4 times per week, with 8,998 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Winnipeg to Chicago O'Hare Intl Airport in the last 72 hours was C$ 491 (round-trip), much lower than the average airfare cost of C$ 639 for United Airlines flights on this route.

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

    Air Canada is also a popular choice for this route. Air Canada flight deals for Winnipeg to Chicago O'Hare Intl Airport start from as low as C$ 365 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around C$ 635. Air Canada operates 4 flights to Chicago O'Hare Intl Airport from Winnipeg in an average week. Users have rated it 7.1/10 across 10,381 reviews.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Schaumburg
Rosemont
Hoffman Estates
Northbrook
Tinley Park
Munster
Hammond
Naperville
Glenview
Great Lakes
Wheeling
Des Plaines
Elk Grove Village
Harvard
Merrillville
Oak Brook
Elmhurst
Kenosha
Skokie
Rockford

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Winnipeg to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?

All flight searches from Winnipeg to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Winnipeg to Chicago?

Once you have performed a search for Winnipeg to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Winnipeg. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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