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Cheap flights from Winnipeg to Chicago from C$ 206

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 9/9. 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

WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
C$ 292WestJet
Find Deal
Wed, 24 Sep - Sat, 27 Sep
WestJet Logo
6:30 a.m. - 4:44 p.m.YWG-ORD
10h 14m2 stops
WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
C$ 315WestJet
Find Deal
Wed, 27 Aug - Wed, 3 Sep
WestJet Logo
6:30 a.m. - 4:43 p.m.YWG-ORD
10h 13m2 stops
WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
C$ 317WestJet
Find Deal
Wed, 24 Sep - Sat, 27 Sep
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 5:40 p.m.ORD-YWG
24h 10m1 stop
C$ 330WestJet
Find Deal
Sat, 6 Sep - Tue, 9 Sep
WestJet Logo
6:30 a.m. - 4:43 p.m.YWG-ORD
10h 13m2 stops
WestJet Logo
5:30 p.m. - 11:26 a.m.ORD-YWG
17h 56m2 stops
C$ 337WestJet
Find Deal
Fri, 19 Sep - Tue, 23 Sep
Logo
7:00 p.m. - 9:51 a.m.YWG-ORD
14h 51m2 stops
Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
C$ 404
Find Deal
Sat, 13 Sep - Sat, 20 Sep
Logo
9:10 a.m. - 9:58 p.m.YWG-ORD
12h 48m1 stop
Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
C$ 426
Find Deal
Sat, 13 Sep - Sat, 20 Sep
Air Canada Logo
12:00 p.m. - 8:11 p.m.YWG-ORD
8h 11m1 stop
Air Canada Logo
10:40 a.m. - 6:59 p.m.ORD-YWG
8h 19m1 stop
C$ 447Air Canada
Find Deal
Fri, 12 Sep - Fri, 19 Sep
United Airlines Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
United Airlines Logo
1:01 p.m. - 3:31 p.m.ORD-YWG
2h 30mdirect
C$ 463United Airlines
Find Deal
Thu, 18 Sep - Sun, 21 Sep
United Airlines Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
United Airlines Logo
1:01 p.m. - 3:31 p.m.ORD-YWG
2h 30mdirect
C$ 465United Airlines
Find Deal
Fri, 12 Sep - Fri, 19 Sep

Air Canada flights from Winnipeg to Chicago O'Hare Intl Airport

Our best Air Canada deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Air Canada
12 Sep
YWG12:00 p.m.Winnipeg
8h 11m
1 stop
ORD8:11 p.m.Chicago O'Hare Intl
19 Sep
ORD10:40 a.m.Chicago O'Hare Intl
8h 19m
1 stop
YWG6:59 p.m.Winnipeg
C$ 447
Find similar
Air Canada
14 Aug
YWG8:10 p.m.Winnipeg
13h 42m
2 stops
ORD9:52 a.m.Chicago O'Hare Intl
16 Aug
ORD10:40 a.m.Chicago O'Hare Intl
8h 19m
1 stop
YWG6:59 p.m.Winnipeg
C$ 589
Find similar
Air Canada
8 Aug
YWG12:00 p.m.Winnipeg
6h 46m
1 stop
ORD6:46 p.m.Chicago O'Hare Intl
11 Aug
ORD7:58 p.m.Chicago O'Hare Intl
2h 35m
YWG10:33 p.m.Winnipeg
C$ 825
Find similar

Delta flights from Winnipeg to Chicago O'Hare Intl Airport

Our best Delta deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Delta
8 Aug
YWG8:35 a.m.Winnipeg
8h 14m
1 stop
ORD4:49 p.m.Chicago O'Hare Intl
11 Aug
ORD6:10 a.m.Chicago O'Hare Intl
5h 39m
1 stop
YWG11:49 a.m.Winnipeg
C$ 843
Find similar
Delta
9 Aug
YWG6:45 a.m.Winnipeg
8h 18m
1 stop
ORD3:03 p.m.Chicago O'Hare Intl
10 Aug
ORD3:54 p.m.Chicago O'Hare Intl
7h 31m
1 stop
YWG11:25 p.m.Winnipeg
C$ 975
Find similar
Delta
5 Aug
YWG6:45 a.m.Winnipeg
8h 18m
1 stop
ORD3:03 p.m.Chicago O'Hare Intl
12 Aug
ORD8:25 a.m.Chicago O'Hare Intl
8h 25m
1 stop
YWG4:50 p.m.Winnipeg
C$ 1,106
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 31 July 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

Wed 24/9

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

1 stop8h 13m

Chicago O'Hare Intl

Sat 27/9

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 292

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 27/8

6:30 a.m.-4:44 p.m.

2 stops10h 14m

Chicago O'Hare Intl

Wed 3/9

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 314

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 24/9

6:30 a.m.-4:43 p.m.

2 stops10h 13m

Chicago O'Hare Intl

Sat 27/9

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 317

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 6/9

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

1 stop8h 13m

Chicago O'Hare Intl

Tue 9/9

5:30 p.m.-5:40 p.m.

1 stop24h 10m

C$ 330

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 19/9

6:30 a.m.-4:43 p.m.

2 stops10h 13m

Chicago O'Hare Intl

Tue 23/9

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

2 stops17h 56m

C$ 337

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 13/9

7:00 p.m.-9:51 a.m.

2 stops14h 51m

Chicago O'Hare Intl

Sat 20/9

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 404

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 13/9

9:10 a.m.-9:58 p.m.

1 stop12h 48m

Chicago O'Hare Intl

Sat 20/9

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 426

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/9

12:00 p.m.-8:11 p.m.

1 stop8h 11m

Chicago O'Hare Intl

Fri 19/9

10:40 a.m.-6:59 p.m.

1 stop8h 19m

C$ 447

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 18/9

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

Chicago O'Hare Intl

Sun 21/9

1:01 p.m.-3:31 p.m.

Nonstop2h 30m

C$ 463

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/9

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

Chicago O'Hare Intl

Fri 19/9

1:01 p.m.-3:31 p.m.

Nonstop2h 30m

C$ 465

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 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 cheapest month to fly to Chicago O'Hare Intl Airport?

In general, August 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$ 510. The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around C$ 556.

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$ 804. 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$ 970.

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$ 701. 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$ 958 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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 625 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Winnipeg for as low as C$ 337 on momondo.

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

There are 4 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 38% 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 July 2025, prices for Winnipeg to Chicago O'Hare Intl Airport flights are approximately 8% more expensive 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$ 206

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$ 206. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 292.
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 2h 31m, 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$ 199Free CancellationRating
7.2
2,978 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 378Free CancellationRating
7.1
9,851 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 510Free CancellationRating
7.4
8,900 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 12 times per week, with 8,900 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$ 370 (round-trip), much lower than the average airfare cost of C$ 495 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$ 274 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around C$ 431. Air Canada operates 14 flights to Chicago O'Hare Intl Airport from Winnipeg in an average week. Users have rated it 7.1/10 across 9,851 reviews.

Travelling to a place near Chicago?

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

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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