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Cheap flights from Winnipeg to Chicago from $216

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:00 am - 5:37 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
11h 37m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:00 am - 6:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
35h 25m2 stops Atlanta Hartsfield-Jackson Calgary
$385Multiple Airlines
Wed, Dec 16 - Sat, Jan 9
Multiple Airlines Logo
7:00 am - 6:20 amYWG  Winnipeg-ORD Chicago O'Hare Intl
24h 20m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:00 am - 6:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
35h 25m2 stops Atlanta Hartsfield-Jackson Calgary
$385Multiple Airlines
Mon, Dec 14 - Sat, Jan 9
Multiple Airlines Logo
7:00 am - 5:37 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
11h 37m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:00 am - 3:40 pmORD  Chicago O'Hare Intl-YWG Winnipeg
8h 40m1 stop Atlanta Hartsfield-Jackson
$387Multiple Airlines
Wed, Dec 16 - Wed, Jan 6
Multiple Airlines Logo
7:00 am - 5:37 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
11h 37m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:00 am - 3:40 pmORD  Chicago O'Hare Intl-YWG Winnipeg
8h 40m1 stop Atlanta Hartsfield-Jackson
$400Multiple Airlines
Wed, Dec 16 - Fri, Jan 8
Air Canada Logo
9:15 am - 2:38 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
6h 23m1 stop Toronto Pearson Intl
Air Canada Logo
1:55 pm - 12:00 pmORD  Chicago O'Hare Intl-YWG Winnipeg
21h 05m1 stop Montreal Pierre Elliott Trudeau Intl
$467Air Canada
Thu, Nov 19 - Sun, Nov 22
Air Canada Logo
3:15 pm - 3:50 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
1h 35mnonstop
Air Canada Logo
7:02 am - 4:09 pmORD  Chicago O'Hare Intl-YWG Winnipeg
8h 07m1 stop Toronto Pearson Intl
$652Air Canada
Fri, Nov 27 - Wed, Dec 2
Air Canada Logo
6:15 am - 10:57 amYWG  Winnipeg-ORD Chicago O'Hare Intl
5h 42m1 stop Toronto Pearson Intl
Air Canada Logo
9:35 am - 2:23 pmORD  Chicago O'Hare Intl-YWG Winnipeg
3h 48mnonstop
$675Air Canada
Thu, Nov 12 - Tue, Nov 17
United Airlines Logo
3:15 pm - 4:02 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
1h 47mnonstop
United Airlines Logo
6:15 pm - 4:09 pmORD  Chicago O'Hare Intl-YWG Winnipeg
20h 54m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl
$729United Airlines
Wed, Dec 23 - Tue, Jan 5
United Airlines Logo
4:05 pm - 8:37 amYWG  Winnipeg-ORD Chicago O'Hare Intl
17h 32m2 stops Toronto Pearson Intl Minneapolis St Paul
United Airlines Logo
6:15 pm - 4:09 pmORD  Chicago O'Hare Intl-YWG Winnipeg
20h 54m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl
$733United Airlines
Mon, Feb 1 - Mon, Feb 8
United Airlines Logo
12:05 pm - 6:55 amYWG  Winnipeg-ORD Chicago O'Hare Intl
19h 50m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County
United Airlines Logo
6:15 pm - 4:09 pmORD  Chicago O'Hare Intl-YWG Winnipeg
20h 54m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl
$738United Airlines
Wed, Dec 23 - Tue, Jan 5

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Air Canada flights from Winnipeg to Chicago

Our best Air Canada deals on Winnipeg to Chicago flight tickets
Air Canada
Nov 19
YWG9:15 amWinnipeg
6h 23m
1 stop
ORD2:38 pmChicago O'Hare Intl
Nov 22
ORD1:55 pmChicago O'Hare Intl
21h 05m
1 stop
YWG12:00 pmWinnipeg
$467
Air Canada
Oct 23
YWG8:45 amWinnipeg
9h 45m
1 stop
ORD6:30 pmChicago O'Hare Intl
Nov 26
ORD4:30 pmChicago O'Hare Intl
8h 14m
1 stop
YWG1:44 amWinnipeg
$778
Air Canada
Oct 23
YWG2:00 pmWinnipeg
2h 35m
ORD4:35 pmChicago O'Hare Intl
Nov 26
ORD4:30 pmChicago O'Hare Intl
8h 14m
1 stop
YWG1:44 amWinnipeg
$818

Delta flights from Winnipeg to Chicago

Our best Delta deals on Winnipeg to Chicago flight tickets
Delta
Oct 17
YWG12:38 pmWinnipeg
8h 49m
1 stop
ORD9:27 pmChicago O'Hare Intl
Dec 25
ORD7:25 amChicago O'Hare Intl
17h 19m
2 stops
YWG1:44 amWinnipeg
$738
Delta
Oct 17
YWG6:40 amWinnipeg
5h 00m
1 stop
ORD11:40 amChicago O'Hare Intl
Dec 25
ORD6:23 amChicago O'Hare Intl
18h 21m
1 stop
YWG1:44 amWinnipeg
$753
Delta
Oct 17
YWG12:38 pmWinnipeg
8h 49m
1 stop
ORD9:27 pmChicago O'Hare Intl
Dec 22
ORD6:23 amChicago O'Hare Intl
6h 02m
1 stop
YWG1:25 pmWinnipeg
$825

momondo Fare Finder

 
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 12/16

7:00 am-5:37 pm

1 stop11h 37m

Chicago O'Hare Intl

Sat 1/9

6:00 am-6:25 pm

2 stops35h 25m

$385

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

7:00 am-6:20 am

1 stop24h 20m

Chicago O'Hare Intl

Sat 1/9

6:00 am-6:25 pm

2 stops35h 25m

$385

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 12/16

7:00 am-5:37 pm

1 stop11h 37m

Chicago O'Hare Intl

Wed 1/6

6:00 am-3:40 pm

1 stop8h 40m

$387

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 12/16

7:00 am-5:37 pm

1 stop11h 37m

Chicago O'Hare Intl

Fri 1/8

6:00 am-3:40 pm

1 stop8h 40m

$400

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 11/19

9:15 am-2:38 pm

1 stop6h 23m

Chicago O'Hare Intl

Sun 11/22

1:55 pm-12:00 pm

1 stop21h 05m

$467

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 11/27

3:15 pm-3:50 pm

Nonstop1h 35m

Chicago O'Hare Intl

Wed 12/2

7:02 am-4:09 pm

1 stop8h 07m

$652
Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 11/12

6:15 am-10:57 am

1 stop5h 42m

Chicago O'Hare Intl

Tue 11/17

9:35 am-2:23 pm

Nonstop3h 48m

$675

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 12/23

3:15 pm-4:02 pm

Nonstop1h 47m

Chicago O'Hare Intl

Tue 1/5

6:15 pm-4:09 pm

2 stops20h 54m

$729

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 2/1

4:05 pm-8:37 am

2 stops17h 32m

Chicago O'Hare Intl

Mon 2/8

6:15 pm-4:09 pm

2 stops20h 54m

$733

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 12/23

12:05 pm-6:55 am

2 stops19h 50m

Chicago O'Hare Intl

Tue 1/5

6:15 pm-4:09 pm

2 stops20h 54m

$738

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

Prices are currently low for flights on this route.

Typical prices usually range from $474 to $699.
The lowest price recently found on this route was $385.

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Winnipeg, with most prices found around $491. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Winnipeg to Chicago during February average around $523.

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 Saturday when prices can be found for as low as $612. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago for around $750.

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 morning. Flights from Winnipeg to Chicago during this time can be as low as $669. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $699.

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?

You could potentially save up to 37% 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 2026, prices for Winnipeg to Chicago flights are approximately 24% 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

$216

Fastest flight time

1h 31m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is $216. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $385.
The fastest flight from Winnipeg to Chicago takes 1h 31m
Direct flights go from Winnipeg to Chicago every day.
There are 3 airports in Chicago. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Winnipeg to Chicago

  • How far is Winnipeg to Chicago by plane?

    There are 716.4 mi between Winnipeg and Chicago. By plane, this route typically takes 1h 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 $517Free CancellationRating
7.4
10,366 reviews
Search United Airlines flights
Air CanadaPriceFrom $563Free CancellationRating
7.1
11,775 reviews
Search Air Canada flights

  • United Airlines Flights From Winnipeg to Chicago

    United Airlines flight deals from Winnipeg to Chicago start from $517 round-trip. Over the 12 United Airlines flights for this route in a normal week, average airfare is usually $702 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 11,775 reviews) operates around 14 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around $1,130, with deals from around $563 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
Portage
Saint Joseph
Lansing
Benton Harbor
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

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