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Cheap flights from Winnipeg to Chicago from C$ 238

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 5/6. 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.
WestJet Logo
6:00 a.m. - 4:40 p.m.
YWG
-
ORD
10h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 316WestJet
Sat, 23 May - Sat, 30 May
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 373WestJet
Wed, 10 Jun - Mon, 15 Jun
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 384WestJet
Sat, 5 Sep - Tue, 8 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 395WestJet
Sat, 5 Sep - Tue, 8 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 419WestJet
Fri, 25 Sep - Sun, 27 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 448WestJet
Fri, 21 Aug - Mon, 24 Aug
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 451WestJet
Mon, 1 Jun - Mon, 8 Jun
WestJet Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m
1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
C$ 452WestJet
Mon, 2 Nov - Mon, 23 Nov
WestJet Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m
1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
C$ 472WestJet
Sun, 1 Nov - Fri, 27 Nov
WestJet Logo
9:00 p.m. - 2:35 p.m.
YWG
-
ORD
17h 35m
1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
C$ 514WestJet
Sat, 31 Oct - Mon, 23 Nov

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
23 May
YWG6:00 a.m.Winnipeg
10h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
30 May
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 316
WestJet
10 Jun
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
15 Jun
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 373
WestJet
5 Sep
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
8 Sep
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 384

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
13 May
YWG2:00 p.m.Winnipeg
2h 35m
ORD4:35 p.m.Chicago O'Hare Intl
8 Jun
ORD8:00 p.m.Chicago O'Hare Intl
2h 38m
YWG10:38 p.m.Winnipeg
C$ 1,202
Air Canada
13 May
YWG2:00 p.m.Winnipeg
2h 35m
ORD4:35 p.m.Chicago O'Hare Intl
17 May
ORD9:55 a.m.Chicago O'Hare Intl
6h 23m
1 stop
YWG4:18 p.m.Winnipeg
C$ 1,240
Air Canada
12 May
YWG11:00 a.m.Winnipeg
9h 08m
1 stop
ORD8:08 p.m.Chicago O'Hare Intl
14 May
ORD9:18 a.m.Chicago O'Hare Intl
2h 34m
YWG11:52 a.m.Winnipeg
C$ 1,256

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 7 May 2026.
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

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 23/5

6:00 a.m.-4:40 p.m.

1 stop10h 40m

Chicago O'Hare Intl

Sat 30/5

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

1 stop7h 25m

C$ 316

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 10/6

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 15/6

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

1 stop7h 25m

C$ 373

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 5/9

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

1 stop9h 40m

Chicago O'Hare Intl

Tue 8/9

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

1 stop7h 25m

C$ 384

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 5/9

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

1 stop9h 40m

Chicago O'Hare Intl

Tue 8/9

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

1 stop7h 25m

C$ 395

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 25/9

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

1 stop9h 40m

Chicago O'Hare Intl

Sun 27/9

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

1 stop7h 25m

C$ 419

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 21/8

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 24/8

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

1 stop7h 25m

C$ 448

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 1/6

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 8/6

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

1 stop7h 25m

C$ 451
Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 2/11

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

1 stop7h 20m

Chicago O'Hare Intl

Mon 23/11

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 452

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 1/11

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

1 stop7h 20m

Chicago O'Hare Intl

Fri 27/11

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 472

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 31/10

9:00 p.m.-2:35 p.m.

1 stop17h 35m

Chicago O'Hare Intl

Mon 23/11

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 514

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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$ 480. The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around C$ 482.

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 Friday when prices can be found for as low as C$ 768. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, 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$ 1,065.

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

In the morning 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$ 821. Flying to Chicago O'Hare Intl Airport in the morning is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 941 on average. Flights to Chicago O'Hare Intl Airport from Winnipeg at noon 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

Can stopping save me money on Winnipeg to Chicago O'Hare Intl Airport flights?

You could potentially save up to 42% 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?

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$ 396

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$ 396. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 593.
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

Frequently asked questions about flying from Winnipeg to Chicago O'Hare Intl Airport

  • 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 21m, 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$ 266Free CancellationRating
7.2
3,331 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 359Free CancellationRating
7.1
11,004 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 474Free CancellationRating
7.4
9,690 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 7 times per week, with 9,690 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$ 474 (round-trip), much lower than the average airfare cost of C$ 632 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$ 359 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around C$ 755. Air Canada operates 7 flights to Chicago O'Hare Intl Airport from Winnipeg in an average week. Users have rated it 7.1/10 across 11,004 reviews.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Schaumburg
Des Plaines
Merrillville
Rosemont
Northbrook
Tinley Park
Evanston
Downers Grove
Skokie
Great Lakes
Wheeling
Hammond
Glenview
Harvey
Naperville
Munster
Hoffman Estates
Harvard
Elmhurst
DeKalb

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.

An easier way to manage your Chicago O'Hare Intl Airport trip

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