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Cheap flights from Winnipeg to Chicago from $137

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 11/18. 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 am - 12:05 pmYWG-ORD
28h 35m2 stops
6:33 pm - 3:10 pmORD-YWG
20h 37m2 stops
Tue, Dec 10 - Thu, Dec 12
5:00 pm - 4:35 amYWG-ORD
11h 35m2 stops
5:15 am - 3:10 pmORD-YWG
9h 55m1 stop
Fri, Nov 22 - Tue, Nov 26
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$402United Airlines
Find Deal
Mon, Feb 3 - Tue, Feb 4
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
7:10 am - 1:27 pmORD-YWG
6h 17m1 stop
$412United Airlines
Find Deal
Tue, Dec 10 - Thu, Dec 12
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
7:20 am - 4:24 pmORD-YWG
9h 04m1 stop
$413Air Canada
Find Deal
Mon, Feb 3 - Sun, Feb 9
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
7:10 am - 1:27 pmORD-YWG
6h 17m1 stop
$418Air Canada
Find Deal
Thu, Jan 16 - Sun, Jan 19
6:55 am - 1:31 pmYWG-MDW
6h 36m1 stop
2:15 pm - 11:34 pmMDW-YWG
9h 19m1 stop
$420Delta
Find Deal
Tue, Dec 10 - Thu, Dec 12
6:55 am - 1:35 pmYWG-MDW
6h 40m1 stop
7:17 pm - 11:27 pmMDW-YWG
4h 10m1 stop
$443Delta
Find Deal
Wed, Nov 27 - Tue, Dec 3
6:55 am - 5:44 pmYWG-MDW
10h 49m1 stop
4:50 pm - 11:52 amMDW-YWG
19h 02m1 stop
$472WestJet
Find Deal
Fri, Dec 20 - Wed, Dec 25
5:00 am - 6:48 pmYWG-ORD
13h 48m2 stops
6:20 am - 11:20 pmORD-YWG
17h 00m2 stops
$479WestJet
Find Deal
Fri, Dec 20 - Wed, Dec 25
7:30 am - 10:38 amYWG-MDW
27h 08m1 stop
Mon, Nov 18
7:30 am - 11:51 pmYWG-ORD
16h 21m1 stop
Sun, Dec 8
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$226United Airlines
Find Deal
Thu, Jan 9
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
$231Air Canada
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Thu, Jan 9
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$232Air Canada
Find Deal
Fri, Jan 10
12:45 pm - 9:15 pmYWG-ORD
8h 30m2 stops
$237Delta
Find Deal
Sat, Jan 11
6:55 am - 1:35 pmYWG-MDW
6h 40m1 stop
$260Delta
Find Deal
Mon, Nov 25
12:20 pm - 9:55 amYWG-ORD
21h 35m2 stops
$264WestJet
Find Deal
Fri, Jan 10
5:00 am - 12:50 pmYWG-MDW
31h 50m2 stops
$269WestJet
Find Deal
Sun, Dec 8
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
$345United Airlines
Find Deal
Mon, Nov 18
8:15 pm - 2:41 pmYWG-ORD
18h 26m2 stops
9:55 pm - 3:10 pmORD-YWG
17h 15m1 stop
Sat, Nov 9 - Mon, Nov 11
7:15 am - 7:43 pmYWG-ORD
12h 28m1 stop
5:00 am - 9:09 pmORD-YWG
16h 09m2 stops
Thu, Nov 7 - Tue, Nov 12
6:45 pm - 10:20 amYWG-MDW
15h 35m1 stop
5:35 pm - 10:45 amMDW-YWG
17h 10m1 stop
$867Porter Airlines
Find Deal
Sat, Nov 9 - Sun, Nov 10
5:00 am - 4:40 pmYWG-MDW
11h 40m1 stop
11:15 am - 10:45 amMDW-YWG
23h 30m1 stop
$885Porter Airlines
Find Deal
Thu, Nov 7 - Tue, Nov 12
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
6:38 pm - 8:28 amORD-YWG
13h 50m1 stop
$923Air Canada
Find Deal
Thu, Nov 7 - Mon, Nov 11
12:15 pm - 7:32 pmYWG-ORD
7h 17m1 stop
7:20 am - 4:18 pmORD-YWG
8h 58m1 stop
$928Air Canada
Find Deal
Sat, Nov 9 - Sun, Nov 10
5:00 am - 9:05 pmYWG-ORD
16h 05m2 stops
6:00 am - 11:27 pmORD-YWG
17h 27m1 stop
$956WestJet
Find Deal
Wed, Nov 6 - Sun, Nov 10
8:45 am - 4:21 pmYWG-ORD
31h 36m2 stops
6:00 am - 11:31 amORD-YWG
5h 31m1 stop
$992WestJet
Find Deal
Thu, Nov 7 - Sun, Nov 10
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$1,002United Airlines
Find Deal
Thu, Nov 7 - Mon, Nov 11
12:15 pm - 7:32 pmYWG-ORD
7h 17m1 stop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$1,007United Airlines
Find Deal
Sat, Nov 9 - Mon, Nov 11
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$402United Airlines
Find Deal
Mon, Feb 3 - Tue, Feb 4
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$415Air Canada
Find Deal
Sun, Dec 22 - Tue, Dec 31
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$427Air Canada
Find Deal
Thu, Nov 28 - Thu, Dec 5
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$437United Airlines
Find Deal
Tue, Nov 26 - Sat, Dec 7
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$441United Airlines
Find Deal
Mon, Dec 23 - Tue, Jan 7
2:15 pm - 4:36 pmYWG-ORD
2h 21mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$467Air Canada
Find Deal
Wed, Apr 9 - Sat, May 24
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$473United Airlines
Find Deal
Mon, Feb 3 - Sun, Feb 9
2:15 pm - 4:36 pmYWG-ORD
2h 21mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$481United Airlines
Find Deal
Sat, Mar 22 - Mon, Mar 31
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$497Air Canada
Find Deal
Tue, Dec 10 - Thu, Dec 12
2:15 pm - 4:36 pmYWG-ORD
2h 21mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$550Air Canada
Find Deal
Sat, Mar 22 - Tue, Apr 1

United Airlines flights from Winnipeg to Chicago

Our best United Airlines deals on Winnipeg to Chicago flight tickets
United Airlines
Feb 3
YWG2:15 pmWinnipeg
2h 36m
ORD4:51 pmChicago O'Hare Intl
Feb 4
ORD12:56 pmChicago O'Hare Intl
2h 32m
YWG3:28 pmWinnipeg
United Airlines
Dec 10
YWG2:15 pmWinnipeg
2h 30m
ORD4:45 pmChicago O'Hare Intl
Dec 12
ORD7:10 amChicago O'Hare Intl
6h 17m
1 stop
YWG1:27 pmWinnipeg
United Airlines
Dec 10
YWG2:15 pmWinnipeg
2h 30m
ORD4:45 pmChicago O'Hare Intl
Dec 12
ORD9:36 pmChicago O'Hare Intl
15h 51m
1 stop
YWG1:27 pmWinnipeg

Air Canada flights from Winnipeg to Chicago

Our best Air Canada deals on Winnipeg to Chicago flight tickets
Air Canada
Feb 3
YWG7:45 amWinnipeg
7h 00m
1 stop
ORD2:45 pmChicago O'Hare Intl
Feb 9
ORD7:20 amChicago O'Hare Intl
9h 04m
1 stop
YWG4:24 pmWinnipeg
Air Canada
Jan 16
YWG7:45 amWinnipeg
7h 00m
1 stop
ORD2:45 pmChicago O'Hare Intl
Jan 19
ORD7:10 amChicago O'Hare Intl
6h 17m
1 stop
YWG1:27 pmWinnipeg
Air Canada
Nov 28
YWG2:15 pmWinnipeg
2h 30m
ORD4:45 pmChicago O'Hare Intl
Dec 5
ORD12:52 pmChicago O'Hare Intl
2h 36m
YWG3:28 pmWinnipeg

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. Most expensive is January

What is the cheapest day to depart Winnipeg for Chicago?

Thursday. The cheapest day of the week is typically Thursday. The most expensive is typically Sunday

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

In the afternoon. Winnipeg to Chicago flights are approximately 4% more expensive at noon than in the afternoon

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

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

What is the cheapest Winnipeg to Chicago flight route?

Winnipeg - Chicago Midway. Fly from Winnipeg to Chicago Midway for the best Winnipeg - Chicago flight prices

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

23 days before. The cheapest time to buy a flight from Winnipeg to Chicago is approximately 23 days to departure

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

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

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

As of November 2024, 21 flights take off from Winnipeg and land in Chicago each week. The most common flight departure day for this route is Sunday, with 14% of weekly flights taking off on this day.

What cabin class options are available on Winnipeg to Chicago flights?

There are 2 cabin classes available to choose from on Winnipeg to Chicago 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 flights?

You could potentially save up to 39% 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.

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

$137

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 $137. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $337.
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?

    There are 716.4 mi between Winnipeg and Chicago. By plane, this route typically takes 2h 30m.

  • 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 a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Winnipeg Airport to Chicago.

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

    The necessary travel and health documents for your Chicago 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?

  • 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 $289Free CancellationRating
7.0
8,123 reviews
Search Air Canada flights
DeltaPriceFrom $370Free CancellationRating
8.0
8,829 reviews
Search Delta flights
United AirlinesPriceFrom $441Free CancellationRating
7.4
9,226 reviews
Search United Airlines flights
  • United Airlines Flights From Winnipeg to Chicago

    United Airlines flight deals from Winnipeg to Chicago start from $441 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $533 round-trip - but some users have found much cheaper deals with momondo.

  • Air Canada Flights From Winnipeg to Chicago

    Air Canada (7.0/10 from 8,123 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around $556, with deals from around $289 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?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Winnipeg.

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?

momondo provides multiple filters to help you find the best flight to Chicago from Winnipeg. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Winnipeg are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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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 78.5 mi from Chicago