Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Chicago from C$ 187

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 9/12. 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

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
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.

Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Winnipeg to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Winnipeg to Chicago.

Cheap last-minute flights

Planning a quick getaway from Winnipeg to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Winnipeg to Chicago

Find recent round-trip train or bus tickets from Winnipeg to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
7:30 a.m. - 5:53 p.m.YWG-MDW
10h 23m1 stop
6:40 a.m. - 3:10 p.m.MDW-YWG
8h 30m1 stop
C$ 369
Find Deal
Fri, 24 Jan - Fri, 31 Jan
7:30 a.m. - 12:33 a.m.YWG-ORD
17h 03m2 stops
6:33 p.m. - 3:10 p.m.ORD-YWG
20h 37m2 stops
C$ 500
Find Deal
Fri, 6 Dec - Thu, 12 Dec
8:15 a.m. - 3:56 p.m.YWG-ORD
7h 41m1 stop
4:45 p.m. - 12:44 a.m.ORD-YWG
7h 59m1 stop
C$ 545WestJet
Find Deal
Thu, 13 Mar - Mon, 17 Mar
6:20 a.m. - 3:56 p.m.YWG-ORD
9h 36m1 stop
4:45 p.m. - 12:44 a.m.ORD-YWG
7h 59m1 stop
C$ 548WestJet
Find Deal
Mon, 14 Apr - Thu, 24 Apr
7:30 a.m. - 2:51 p.m.YWG-ORD
7h 21m1 stop
7:19 a.m. - 1:58 p.m.ORD-YWG
6h 39m1 stop
C$ 565Air Canada
Find Deal
Sat, 14 Dec - Wed, 18 Dec
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
7:20 a.m. - 4:28 p.m.ORD-YWG
9h 08m1 stop
C$ 588Air Canada
Find Deal
Fri, 24 Jan - Fri, 31 Jan
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
9:50 a.m. - 5:18 p.m.ORD-YWG
7h 28m1 stop
C$ 597United Airlines
Find Deal
Tue, 14 Jan - Sun, 16 Feb
5:37 p.m. - 9:58 p.m.YWG-ORD
4h 21m1 stop
6:55 a.m. - 4:47 p.m.ORD-YWG
9h 52m2 stops
C$ 598Delta
Find Deal
Tue, 7 Jan - Tue, 14 Jan
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 601United Airlines
Find Deal
Wed, 18 Dec - Wed, 25 Dec
5:37 p.m. - 9:58 p.m.YWG-ORD
4h 21m1 stop
11:50 a.m. - 4:47 p.m.ORD-YWG
4h 57m1 stop
C$ 629Delta
Find Deal
Mon, 6 Jan - Tue, 14 Jan
7:30 a.m. - 11:42 a.m.YWG-MDW
28h 12m1 stop
C$ 187
Find Deal
Mon, 9 Dec
7:30 a.m. - 5:50 p.m.YWG-MDW
10h 20m1 stop
C$ 200
Find Deal
Fri, 10 Jan
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 319Air Canada
Find Deal
Thu, 9 Jan
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 328Air Canada
Find Deal
Fri, 10 Jan
7:30 a.m. - 1:11 p.m.YWG-ORD
5h 41m1 stop
C$ 334United Airlines
Find Deal
Thu, 9 Jan
6:55 a.m. - 6:14 p.m.YWG-MDW
11h 19m2 stops
C$ 337Delta
Find Deal
Fri, 10 Jan
5:00 a.m. - 12:55 p.m.YWG-ORD
7h 55m2 stops
C$ 382Delta
Find Deal
Thu, 9 Jan
7:30 a.m. - 1:11 p.m.YWG-ORD
5h 41m1 stop
C$ 408United Airlines
Find Deal
Thu, 2 Jan
12:20 p.m. - 11:26 a.m.YWG-ORD
23h 06m2 stops
C$ 816WestJet
Find Deal
Thu, 26 Dec
8:25 p.m. - 9:23 a.m.YWG-MDW
12h 58m2 stops
C$ 903WestJet
Find Deal
Thu, 26 Dec
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 590Air Canada
Find Deal
Thu, 9 Jan - Tue, 14 Jan
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 601United Airlines
Find Deal
Wed, 18 Dec - Wed, 25 Dec
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 621Air Canada
Find Deal
Fri, 24 Jan - Fri, 31 Jan
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
12:58 p.m. - 3:28 p.m.ORD-YWG
2h 30mdirect
C$ 622United Airlines
Find Deal
Sun, 9 Feb - Thu, 20 Feb
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
C$ 636Air Canada
Find Deal
Sat, 14 Dec - Wed, 18 Dec
2:15 p.m. - 4:37 p.m.YWG-ORD
2h 22mdirect
12:58 p.m. - 3:28 p.m.ORD-YWG
2h 30mdirect
C$ 637United Airlines
Find Deal
Wed, 26 Mar - Sat, 29 Mar
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
C$ 651United Airlines
Find Deal
Sat, 14 Dec - Wed, 18 Dec
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 664Air Canada
Find Deal
Mon, 6 Jan - Wed, 15 Jan
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
C$ 681Air Canada
Find Deal
Wed, 4 Dec - Wed, 11 Dec
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
C$ 725United Airlines
Find Deal
Sat, 7 Dec - Tue, 10 Dec

United Airlines flights from Winnipeg to Chicago

Our best United Airlines deals on Winnipeg to Chicago flight tickets
United Airlines
14 Jan
YWG2:15 p.m.Winnipeg
2h 36m
ORD4:51 p.m.Chicago O'Hare Intl
16 Feb
ORD9:50 a.m.Chicago O'Hare Intl
7h 28m
1 stop
YWG5:18 p.m.Winnipeg
United Airlines
18 Dec
YWG2:15 p.m.Winnipeg
2h 30m
ORD4:45 p.m.Chicago O'Hare Intl
25 Dec
ORD12:56 p.m.Chicago O'Hare Intl
2h 32m
YWG3:28 p.m.Winnipeg
United Airlines
9 Feb
YWG2:15 p.m.Winnipeg
2h 36m
ORD4:51 p.m.Chicago O'Hare Intl
20 Feb
ORD12:58 p.m.Chicago O'Hare Intl
2h 30m
YWG3:28 p.m.Winnipeg

Air Canada flights from Winnipeg to Chicago

Our best Air Canada deals on Winnipeg to Chicago flight tickets
Air Canada
14 Dec
YWG7:30 a.m.Winnipeg
7h 21m
1 stop
ORD2:51 p.m.Chicago O'Hare Intl
18 Dec
ORD7:19 a.m.Chicago O'Hare Intl
6h 39m
1 stop
YWG1:58 p.m.Winnipeg
Air Canada
24 Jan
YWG7:45 a.m.Winnipeg
7h 00m
1 stop
ORD2:45 p.m.Chicago O'Hare Intl
31 Jan
ORD7:20 a.m.Chicago O'Hare Intl
9h 08m
1 stop
YWG4:28 p.m.Winnipeg
Air Canada
10 Feb
YWG7:45 a.m.Winnipeg
7h 00m
1 stop
ORD2:45 p.m.Chicago O'Hare Intl
18 Feb
ORD7:20 a.m.Chicago O'Hare Intl
9h 04m
1 stop
YWG4:24 p.m.Winnipeg

See travel insights to Chicago from

How to get the cheapest flight ticket from Winnipeg to Chicago

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 from Winnipeg to Chicago?

June. The cheapest time of year to fly to Chicago from Winnipeg is June. The most expensive is January.

What is the cheapest day to depart Winnipeg for Chicago?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Saturday

When is the cheapest time to fly from Winnipeg to Chicago?

In the morning. Winnipeg to Chicago flights are approximately 19% more expensive in the evening than in the morning

What is the cheapest Winnipeg to Chicago flight route?

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

How far in advance should you book Winnipeg to Chicago flights?

14 days before. The cheapest time to buy a flight from Winnipeg to Chicago is approximately 14 days to departure

Can stopping save me money on Winnipeg to Chicago flights?

You could potentially save up to 41% on your flight if you consider stops on a Winnipeg to Chicago flight.

How have Winnipeg to Chicago flight prices changed over time?

As of November 2024, prices for Winnipeg to Chicago flights are approximately 17% more expensive when compared to flights at the same time last year.

What is the typical price of a round-trip flight between Winnipeg and Chicago?


When to book flights from Winnipeg to Chicago

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

Cheap Winnipeg to Chicago (YWG to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago

Best price found

C$ 187

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is C$ 187. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 369.
The fastest flight from Winnipeg to Chicago takes 2h 21m
Direct flights go from Winnipeg to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Winnipeg to Chicago by plane?

    A flight from Winnipeg to Chicago will travel around 1153.0 km. 2h 21m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Winnipeg Airport to Chicago?

    Prices for flights from Winnipeg Airport to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Winnipeg Airport to Chicago?

  • How old do you have to be to fly from Winnipeg Airport to Chicago?

    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 Winnipeg Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Winnipeg to Chicago?

  • What is the most popular airline from Winnipeg to Chicago?


Best airlines flying from Winnipeg to Chicago

Compare and see reviews for airlines that fly from Winnipeg to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 395Free CancellationRating
7.0
8,238 reviews
Search Air Canada flights
DeltaPriceFrom C$ 484Free CancellationRating
8.0
8,759 reviews
Search Delta flights
WestJetPriceFrom C$ 514Free CancellationRating
7.3
2,810 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 551Free CancellationRating
7.4
9,173 reviews
Search United Airlines flights
  • United Airlines Flights From Winnipeg to Chicago

    United Airlines operates around 7 flights from Winnipeg to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 524, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 394 round-trip. United Airlines has been scored 7.4/10 in 9,173 reviews.

  • Air Canada Flights From Winnipeg to Chicago

    Air Canada (7.0/10 from 8,238 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 481, with deals from around C$ 282 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.


Why use momondo?

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

Finding the right flight to Chicago from Winnipeg 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 Chicago quick and easy, saving you time and money.

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

momondo does allow users to show only those flights to Chicago from Winnipeg which offer a flexible booking policy as well as other useful filters and features.

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 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 26/11
Tue 3/12
Email me momondo's favourite deals

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago