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Cheap flights from Winnipeg to Chicago from $126

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 10/31. 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
0 bags

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Cheap round-trip flights

WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 9:01 amORD-YWG
15h 31m1 stop
$195WestJet
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Sun, Oct 12 - Sun, Oct 19
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 9:01 amORD-YWG
15h 31m1 stop
$204WestJet
Find Deal
Fri, Oct 17 - Sun, Oct 19
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 11:26 amORD-YWG
17h 56m2 stops
$217WestJet
Find Deal
Fri, Oct 17 - Sun, Oct 19
Multiple Airlines Logo
9:00 pm - 6:39 pmYWG-MDW
21h 39m2 stops
Multiple Airlines Logo
1:37 pm - 3:07 pmMDW-YWG
25h 30m1 stop
$218Multiple Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Multiple Airlines Logo
7:30 am - 6:39 pmYWG-MDW
11h 09m1 stop
Multiple Airlines Logo
5:20 am - 2:07 pmMDW-YWG
8h 47m1 stop
$231Multiple Airlines
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Fri, Oct 31 - Sun, Nov 2
United Airlines Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
United Airlines Logo
5:01 am - 1:09 pmORD-YWG
8h 08m1 stop
$341United Airlines
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Thu, Oct 16 - Sun, Oct 19
United Airlines Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
United Airlines Logo
1:01 pm - 3:31 pmORD-YWG
2h 30mnonstop
$342United Airlines
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Thu, Oct 9 - Sun, Oct 12
Delta Logo
6:40 am - 1:08 pmYWG-MDW
6h 28m1 stop
Delta Logo
9:20 am - 4:50 pmMDW-YWG
7h 30m1 stop
$447Delta
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Thu, Oct 9 - Sun, Oct 12
Delta Logo
12:40 pm - 6:08 pmYWG-MDW
5h 28m1 stop
Delta Logo
6:00 am - 3:09 pmMDW-YWG
9h 09m1 stop
$553Delta
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Tue, Mar 3 - Sun, Mar 8
Porter Airlines Logo
4:25 pm - 11:50 amYWG-MDW
19h 25m2 stops
Porter Airlines Logo
11:00 am - 11:13 amMDW-YWG
24h 13m2 stops
$796Porter Airlines
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Fri, Oct 31 - Sun, Nov 2

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
Oct 12
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 19
ORD5:30 pmChicago O'Hare Intl
15h 31m
1 stop
YWG9:01 amWinnipeg
$195
Find similar
WestJet
Oct 17
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 19
ORD5:30 pmChicago O'Hare Intl
15h 31m
1 stop
YWG9:01 amWinnipeg
$204
Find similar
WestJet
Oct 17
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 19
ORD5:30 pmChicago O'Hare Intl
17h 56m
2 stops
YWG11:26 amWinnipeg
$217
Find similar

United Airlines flights from Winnipeg to Chicago

Our best United Airlines deals on Winnipeg to Chicago flight tickets
United Airlines
Oct 16
YWG7:00 amWinnipeg
2h 31m
ORD9:31 amChicago O'Hare Intl
Oct 19
ORD5:01 amChicago O'Hare Intl
8h 08m
1 stop
YWG1:09 pmWinnipeg
$341
Find similar
United Airlines
Oct 9
YWG2:20 pmWinnipeg
2h 31m
ORD4:51 pmChicago O'Hare Intl
Oct 12
ORD1:01 pmChicago O'Hare Intl
2h 30m
YWG3:31 pmWinnipeg
$342
Find similar
United Airlines
Oct 9
YWG2:20 pmWinnipeg
2h 31m
ORD4:51 pmChicago O'Hare Intl
Oct 12
ORD5:01 amChicago O'Hare Intl
8h 08m
1 stop
YWG1:09 pmWinnipeg
$343
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Chicago 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 832,500 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 10/12

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-9:01 am

1 stop15h 31m

$195

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/17

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-9:01 am

1 stop15h 31m

$204

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/17

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-11:26 am

2 stops17h 56m

$217

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/30

9:00 pm-6:39 pm

2 stops21h 39m

Chicago Midway

Thu 11/6

1:37 pm-3:07 pm

1 stop25h 30m

$218

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/31

7:30 am-6:39 pm

1 stop11h 09m

Chicago Midway

Sun 11/2

5:20 am-2:07 pm

1 stop8h 47m

$231

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/16

7:00 am-9:31 am

Nonstop2h 31m

Chicago O'Hare Intl

Sun 10/19

5:01 am-1:09 pm

1 stop8h 08m

$341

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/9

2:20 pm-4:51 pm

Nonstop2h 31m

Chicago O'Hare Intl

Sun 10/12

1:01 pm-3:31 pm

Nonstop2h 30m

$342

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/9

6:40 am-1:08 pm

1 stop6h 28m

Chicago Midway

Sun 10/12

9:20 am-4:50 pm

1 stop7h 30m

$447

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

12:40 pm-6:08 pm

1 stop5h 28m

Chicago Midway

Sun 3/8

6:00 am-3:09 pm

1 stop9h 09m

$553

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/31

4:25 pm-11:50 am

2 stops19h 25m

Chicago Midway

Sun 11/2

11:00 am-11:13 am

2 stops24h 13m

$796

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Winnipeg, with most prices found around $363. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Winnipeg to Chicago during October average around $399.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $533. 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 for around $799.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Winnipeg to Chicago during this time can be as low as $440. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $634.

What is the cheapest Winnipeg to Chicago flight route?

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

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

There are 4 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?

No. A direct flight is the cheapest option for a flight between Winnipeg to Chicago.

How have Winnipeg to Chicago flight prices changed over time?

As of September 2025, prices for Winnipeg to Chicago flights are approximately 2% 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

$247

Fastest flight time

2h 21m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Chicago

1 airport
The best one-way flight to Chicago from Winnipeg in the past 72 hours is $247. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $466.
The fastest flight from Winnipeg to Chicago takes 2h 21m
Direct flights go from Winnipeg to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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  • How far is Winnipeg to Chicago by plane?

    There are 716.4 mi between Winnipeg and Chicago. By plane, this route typically takes 2h 31m.

  • 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
United AirlinesPriceFrom $199Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
Air CanadaPriceFrom $230Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

  • United Airlines Flights From Winnipeg to Chicago

    United Airlines flight deals from Winnipeg to Chicago start from $199 round-trip. Over the 14 United Airlines flights for this route in a normal week, average airfare is usually $487 round-trip - but some users have found much cheaper deals with momondo.

  • Air Canada Flights From Winnipeg to Chicago

    Air Canada (7.1/10 from 10,000 reviews) operates around 14 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around $645, with deals from around $230 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

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.

An easier way to manage your Chicago trip

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport