Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Chicago from C$ 169

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 12/1. 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

Discover deals from 900+ travel sites with momondo.

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 Winnipeg to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:00 p.m. - 4:52 p.m.
YWG
-
ORD
19h 52m2 stops
Multiple Airlines Logo
2:53 p.m. - 3:07 p.m.
ORD
-
YWG
24h 14m1 stop
C$ 284Multiple Airlines
Tue, 13 Jan - Tue, 20 Jan
WestJet Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m1 stop
C$ 295WestJet
Fri, 30 Jan - Fri, 6 Feb
Multiple Airlines Logo
7:30 a.m. - 4:52 p.m.
YWG
-
ORD
9h 22m1 stop
Multiple Airlines Logo
11:48 a.m. - 12:43 a.m.
ORD
-
YWG
12h 55m1 stop
C$ 300Multiple Airlines
Wed, 14 Jan - Mon, 19 Jan
Multiple Airlines Logo
9:00 p.m. - 4:52 p.m.
YWG
-
ORD
19h 52m2 stops
Multiple Airlines Logo
2:53 p.m. - 3:07 p.m.
ORD
-
YWG
24h 14m1 stop
C$ 304Multiple Airlines
Tue, 13 Jan - Tue, 20 Jan
Multiple Airlines Logo
5:05 p.m. - 4:52 p.m.
YWG
-
ORD
23h 47m1 stop
Multiple Airlines Logo
8:41 p.m. - 12:43 a.m.
ORD
-
YWG
28h 02m1 stop
C$ 320Multiple Airlines
Fri, 16 Jan - Sun, 18 Jan
WestJet Logo
12:40 p.m. - 4:43 p.m.
YWG
-
ORD
28h 03m1 stop
WestJet Logo
5:30 p.m. - 5:40 p.m.
ORD
-
YWG
24h 10m1 stop
C$ 322WestJet
Sat, 25 Apr - Thu, 30 Apr
Multiple Airlines Logo
4:10 p.m. - 4:51 p.m.
YWG
-
ORD
24h 41m2 stops
Multiple Airlines Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m1 stop
C$ 327Multiple Airlines
Fri, 30 Jan - Fri, 6 Feb
WestJet Logo
5:00 p.m. - 4:43 p.m.
YWG
-
ORD
23h 43m2 stops
WestJet Logo
5:30 p.m. - 2:30 p.m.
ORD
-
YWG
21h 00m1 stop
C$ 329WestJet
Sat, 25 Apr - Thu, 30 Apr
WestJet Logo
5:00 p.m. - 4:43 p.m.
YWG
-
ORD
23h 43m2 stops
WestJet Logo
5:30 p.m. - 11:00 p.m.
ORD
-
YWG
29h 30m1 stop
C$ 331WestJet
Sat, 25 Apr - Thu, 30 Apr
Multiple Airlines Logo
7:30 a.m. - 4:52 p.m.
YWG
-
ORD
9h 22m1 stop
Multiple Airlines Logo
7:31 p.m. - 8:06 p.m.
ORD
-
YWG
24h 35m2 stops
C$ 335Multiple Airlines
Wed, 14 Jan - Mon, 19 Jan

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
14 Apr
YWG12:10 p.m.Winnipeg
7h 25m
1 stop
ORD7:35 p.m.Chicago O'Hare Intl
18 Apr
ORD8:00 a.m.Chicago O'Hare Intl
7h 30m
1 stop
YWG3:30 p.m.Winnipeg
C$ 575
Find similar
Porter Airlines
14 Apr
YWG6:00 a.m.Winnipeg
8h 05m
1 stop
ORD2:05 p.m.Chicago O'Hare Intl
18 Apr
ORD8:00 a.m.Chicago O'Hare Intl
7h 30m
1 stop
YWG3:30 p.m.Winnipeg
C$ 586
Find similar
Porter Airlines
14 Apr
YWG6:00 a.m.Winnipeg
8h 05m
1 stop
ORD2:05 p.m.Chicago O'Hare Intl
18 Apr
ORD8:00 a.m.Chicago O'Hare Intl
7h 30m
1 stop
YWG3:30 p.m.Winnipeg
C$ 623
Find similar

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
30 Jan
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
6 Feb
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
C$ 295
Find similar
WestJet
25 Apr
YWG12:40 p.m.Winnipeg
28h 03m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
24h 10m
1 stop
YWG5:40 p.m.Winnipeg
C$ 322
Find similar
WestJet
12 Jan
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
19 Jan
ORD2:20 p.m.Chicago O'Hare Intl
10h 21m
1 stop
YWG12:41 a.m.Winnipeg
C$ 327
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 18 December 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

Tue 13/1

9:00 p.m.-4:52 p.m.

2 stops19h 52m

Chicago O'Hare Intl

Tue 20/1

2:53 p.m.-3:07 p.m.

1 stop24h 14m

C$ 284

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 30/1

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

1 stop7h 20m

Chicago O'Hare Intl

Fri 6/2

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

1 stop8h 20m

C$ 295

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 14/1

7:30 a.m.-4:52 p.m.

1 stop9h 22m

Chicago O'Hare Intl

Mon 19/1

11:48 a.m.-12:43 a.m.

1 stop12h 55m

C$ 300

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 13/1

9:00 p.m.-4:52 p.m.

2 stops19h 52m

Chicago O'Hare Intl

Tue 20/1

2:53 p.m.-3:07 p.m.

1 stop24h 14m

C$ 304

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 16/1

5:05 p.m.-4:52 p.m.

1 stop23h 47m

Chicago O'Hare Intl

Sun 18/1

8:41 p.m.-12:43 a.m.

1 stop28h 02m

C$ 320

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

12:40 p.m.-4:43 p.m.

1 stop28h 03m

Chicago O'Hare Intl

Thu 30/4

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

1 stop24h 10m

C$ 322

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 30/1

4:10 p.m.-4:51 p.m.

2 stops24h 41m

Chicago O'Hare Intl

Fri 6/2

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

1 stop8h 20m

C$ 327

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

5:00 p.m.-4:43 p.m.

2 stops23h 43m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-2:30 p.m.

1 stop21h 00m

C$ 329

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

5:00 p.m.-4:43 p.m.

2 stops23h 43m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-11:00 p.m.

1 stop29h 30m

C$ 331

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 14/1

7:30 a.m.-4:52 p.m.

1 stop9h 22m

Chicago O'Hare Intl

Mon 19/1

7:31 p.m.-8:06 p.m.

2 stops24h 35m

C$ 335

Flights are sorted by cheapest round-trip flights first.

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

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$ 486. 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$ 510.

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$ 1,005.

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$ 700. 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$ 956 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 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 22% 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 December 2025, prices for Winnipeg to Chicago O'Hare Intl Airport flights are approximately 1% 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$ 486

Fastest flight time

2h 21m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is C$ 486. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 629.
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 on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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 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$ 199Free CancellationRating
7.2
3,204 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 485Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 495Free CancellationRating
7.1
10,534 reviews
Search Air Canada flights

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

    United Airlines flies from Winnipeg to Chicago O'Hare Intl Airport around 3 times per week, with 9,092 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$ 485 (round-trip), much lower than the average airfare cost of C$ 642 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$ 495 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around C$ 729. Air Canada operates 3 flights to Chicago O'Hare Intl Airport from Winnipeg in an average week. Users have rated it 7.1/10 across 10,534 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
Skokie
Hammond
Harvey
Naperville
Glenview
Great Lakes
Wheeling
Elmhurst
Harvard
Merrillville
Elk Grove Village
Oak Brook
Kenosha

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

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
Sat 17/1
Sat 24/1
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago