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Cheap flights from Winnipeg to Chicago from C$ 221

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 27/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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. - 4:56 p.m.YWG-ORD
9h 26m1 stop
5:15 a.m. - 3:10 p.m.ORD-YWG
9h 55m1 stop
C$ 338
Find Deal
Tue, 19 Nov - Fri, 22 Nov
5:00 p.m. - 12:04 p.m.YWG-ORD
19h 04m1 stop
5:00 a.m. - 9:09 p.m.ORD-YWG
16h 09m2 stops
C$ 425
Find Deal
Mon, 11 Nov - Wed, 13 Nov
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
7:20 a.m. - 4:18 p.m.ORD-YWG
8h 58m1 stop
C$ 554Air Canada
Find Deal
Mon, 25 Nov - Sat, 30 Nov
4:30 p.m. - 11:57 p.m.YWG-ORD
7h 27m1 stop
9:36 p.m. - 1:27 p.m.ORD-YWG
15h 51m1 stop
C$ 562United Airlines
Find Deal
Sat, 16 Nov - Mon, 18 Nov
4:30 p.m. - 11:57 p.m.YWG-ORD
7h 27m1 stop
7:10 a.m. - 1:27 p.m.ORD-YWG
6h 17m1 stop
C$ 593United Airlines
Find Deal
Fri, 1 Nov - Wed, 6 Nov
11:50 a.m. - 8:10 p.m.YWG-ORD
8h 20m1 stop
7:20 a.m. - 4:18 p.m.ORD-YWG
8h 58m1 stop
C$ 608Air Canada
Find Deal
Sat, 26 Oct - Wed, 30 Oct
7:30 a.m. - 7:28 p.m.YWG-ORD
11h 58m2 stops
7:05 a.m. - 3:34 p.m.ORD-YWG
8h 29m2 stops
C$ 619WestJet
Find Deal
Sat, 26 Oct - Wed, 30 Oct
5:00 a.m. - 5:54 p.m.YWG-MDW
12h 54m2 stops
9:30 a.m. - 11:41 a.m.MDW-YWG
26h 11m1 stop
C$ 622WestJet
Find Deal
Mon, 11 Nov - Wed, 13 Nov
7:30 a.m. - 2:34 p.m.YWG-MDW
7h 04m1 stop
6:00 a.m. - 3:10 p.m.MDW-YWG
9h 10m1 stop
C$ 667Delta
Find Deal
Tue, 19 Nov - Fri, 22 Nov
6:55 a.m. - 5:03 p.m.YWG-MDW
10h 08m2 stops
6:00 a.m. - 3:10 p.m.MDW-YWG
9h 10m1 stop
C$ 730Delta
Find Deal
Sat, 2 Nov - Wed, 6 Nov
7:30 a.m. - 8:49 p.m.YWG-MDW
13h 19m1 stop
C$ 221
Find Deal
Mon, 27 Jan
7:30 a.m. - 4:31 p.m.YWG-ORD
9h 01m1 stop
C$ 221
Find Deal
Mon, 27 Jan
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
C$ 310Air Canada
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Sat, 23 Nov
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 311United Airlines
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Fri, 10 Jan
6:40 a.m. - 12:33 p.m.YWG-MDW
5h 53m2 stops
C$ 319Delta
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Mon, 27 Jan
6:40 a.m. - 1:14 p.m.YWG-ORD
6h 34m2 stops
C$ 319Delta
Find Deal
Fri, 10 Jan
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
C$ 327Air Canada
Find Deal
Wed, 30 Oct
6:55 a.m. - 6:32 p.m.YWG-MDW
11h 37m1 stop
C$ 367WestJet
Find Deal
Sat, 23 Nov
6:25 p.m. - 6:32 p.m.YWG-MDW
24h 07m2 stops
C$ 410WestJet
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Sat, 23 Nov
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 510United Airlines
Find Deal
Mon, 27 Jan
8:00 a.m. - 9:58 p.m.YWG-ORD
13h 58m1 stop
5:15 a.m. - 3:30 p.m.ORD-YWG
10h 15m1 stop
C$ 753
Find Deal
Thu, 10 Oct - Mon, 14 Oct
6:50 a.m. - 11:33 p.m.YWG-MDW
16h 43m2 stops
7:15 a.m. - 3:30 p.m.MDW-YWG
8h 15m1 stop
C$ 1,045
Find Deal
Fri, 11 Oct - Mon, 14 Oct
8:00 a.m. - 9:03 a.m.YWG-ORD
25h 03m2 stops
10:33 a.m. - 2:30 p.m.ORD-YWG
27h 57m3 stops
C$ 1,162
Find Deal
Thu, 10 Oct - Mon, 14 Oct
4:40 p.m. - 6:15 p.m.YWG-MDW
25h 35m2 stops
8:00 a.m. - 6:02 p.m.MDW-YWG
10h 02m2 stops
C$ 1,203
Find Deal
Fri, 11 Oct - Mon, 14 Oct
8:00 a.m. - 4:48 p.m.YWG-ORD
32h 48m3 stops
7:20 a.m. - 2:30 p.m.ORD-YWG
31h 10m3 stops
C$ 1,352
Find Deal
Thu, 10 Oct - Mon, 14 Oct
8:00 a.m. - 6:02 p.m.YWG-MDW
10h 02m1 stop
7:10 p.m. - 11:31 a.m.MDW-YWG
16h 21m1 stop
C$ 1,356WestJet
Find Deal
Thu, 10 Oct - Mon, 14 Oct
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
9:13 p.m. - 1:25 p.m.ORD-YWG
16h 12m1 stop
C$ 1,374Air Canada
Find Deal
Thu, 10 Oct - Mon, 14 Oct
7:30 a.m. - 10:56 a.m.YWG-ORD
27h 26m2 stops
12:40 p.m. - 11:31 a.m.ORD-YWG
22h 51m1 stop
C$ 1,379WestJet
Find Deal
Thu, 10 Oct - Mon, 14 Oct
12:26 p.m. - 6:29 p.m.YWG-MDW
6h 03m1 stop
9:35 a.m. - 4:33 p.m.MDW-YWG
6h 58m1 stop
C$ 1,465Delta
Find Deal
Fri, 11 Oct - Mon, 14 Oct
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
1:05 p.m. - 3:30 p.m.ORD-YWG
2h 25mdirect
C$ 1,531Air Canada
Find Deal
Thu, 10 Oct - Mon, 14 Oct
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$ 629Air Canada
Find Deal
Mon, 25 Nov - Sat, 30 Nov
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$ 782United Airlines
Find Deal
Tue, 19 Nov - Fri, 22 Nov
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$ 854Air Canada
Find Deal
Tue, 19 Nov - Fri, 22 Nov
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$ 869United Airlines
Find Deal
Sun, 3 Nov - Sun, 10 Nov
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$ 1,017United Airlines
Find Deal
Mon, 11 Nov - Thu, 14 Nov
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$ 1,022United Airlines
Find Deal
Tue, 29 Oct - Thu, 31 Oct
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
1:05 p.m. - 3:30 p.m.ORD-YWG
2h 25mdirect
C$ 1,068United Airlines
Find Deal
Tue, 22 Oct - Thu, 24 Oct
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$ 1,143United Airlines
Find Deal
Mon, 4 Nov - Mon, 11 Nov
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$ 1,158Air Canada
Find Deal
Sat, 16 Nov - Mon, 18 Nov
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$ 1,189Air Canada
Find Deal
Thu, 7 Nov - Sun, 10 Nov

Air Canada flights from Winnipeg to Chicago

Our best Air Canada deals on Winnipeg to Chicago flight tickets
Air Canada
25 Nov
YWG7:45 a.m.Winnipeg
7h 00m
1 stop
ORD2:45 p.m.Chicago O'Hare Intl
30 Nov
ORD7:20 a.m.Chicago O'Hare Intl
8h 58m
1 stop
YWG4:18 p.m.Winnipeg
Air Canada
26 Oct
YWG11:50 a.m.Winnipeg
8h 20m
1 stop
ORD8:10 p.m.Chicago O'Hare Intl
30 Oct
ORD7:20 a.m.Chicago O'Hare Intl
8h 58m
1 stop
YWG4:18 p.m.Winnipeg
Air Canada
25 Nov
YWG2:15 p.m.Winnipeg
2h 30m
ORD4:45 p.m.Chicago O'Hare Intl
30 Nov
ORD12:52 p.m.Chicago O'Hare Intl
2h 36m
YWG3:28 p.m.Winnipeg

United Airlines flights from Winnipeg to Chicago

Our best United Airlines deals on Winnipeg to Chicago flight tickets
United Airlines
16 Nov
YWG4:30 p.m.Winnipeg
7h 27m
1 stop
ORD11:57 p.m.Chicago O'Hare Intl
18 Nov
ORD9:36 p.m.Chicago O'Hare Intl
15h 51m
1 stop
YWG1:27 p.m.Winnipeg
United Airlines
1 Nov
YWG4:30 p.m.Winnipeg
7h 27m
1 stop
ORD11:57 p.m.Chicago O'Hare Intl
6 Nov
ORD7:10 a.m.Chicago O'Hare Intl
6h 17m
1 stop
YWG1:27 p.m.Winnipeg
United Airlines
11 Nov
YWG7:05 p.m.Winnipeg
13h 52m
1 stop
ORD8:57 a.m.Chicago O'Hare Intl
14 Nov
ORD12:52 p.m.Chicago O'Hare Intl
2h 36m
YWG3:28 p.m.Winnipeg

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 evening. Winnipeg to Chicago flights are approximately 13% more expensive in the afternoon than in the evening

What is the cheapest airline that flies to Chicago from Winnipeg?

Delta. Delta, Air Canada, and United Airlines are the most popular carriers operating from Winnipeg to Chicago

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?

16 days before. The cheapest time to buy a flight from Winnipeg to Chicago is approximately 16 days to departure

How many flights depart from Winnipeg to Chicago on average per day?

As of October 2024, 3 flights take off from Winnipeg and land in Chicago each day. The most common flight departure time for this route is 2:00p.m., with 100% of daily flights taking off in the afternoon.

How many flights depart from Winnipeg to Chicago on average per week?

As of October 2024, there are 21 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Sunday, with 14% of flights taking off on this day.

Can stopping save me money on Winnipeg to Chicago flights?

You could potentially save up to 28% 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 October 2024, prices for Winnipeg to Chicago flights are approximately 28% more expensive when compared to flights at the same time last year.

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$ 221

Fastest flight time

2h 30m

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$ 221. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 338.
The fastest flight from Winnipeg to Chicago takes 2h 30m
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 30m 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$ 445Free CancellationRating
6.9
7,860 reviews
Search Air Canada flights
DeltaPriceFrom C$ 470Free CancellationRating
8.0
8,974 reviews
Search Delta flights
WestJetPriceFrom C$ 499Free CancellationRating
7.3
2,807 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 535Free CancellationRating
7.4
9,381 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 9,381 reviews.

  • Air Canada Flights From Winnipeg to Chicago

    Air Canada (6.9/10 from 7,860 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 492, with deals from around C$ 328 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.


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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