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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
7:55 pm - 6:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
22h 45m1 stop Toronto Pearson Intl
Multiple Airlines Logo
6:20 pm - 9:15 amORD  Chicago O'Hare Intl-YWG Winnipeg
14h 55m1 stop Toronto Island
$377Multiple Airlines
Sun, Dec 13 - Tue, Dec 15
Multiple Airlines Logo
7:55 pm - 12:35 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
16h 40m1 stop Toronto Pearson Intl
Multiple Airlines Logo
6:20 pm - 9:15 amORD  Chicago O'Hare Intl-YWG Winnipeg
14h 55m1 stop Toronto Island
$381Multiple Airlines
Mon, Dec 14 - Wed, Dec 16
Multiple Airlines Logo
7:55 pm - 12:35 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
16h 40m1 stop Toronto Pearson Intl
Multiple Airlines Logo
6:20 pm - 9:15 amORD  Chicago O'Hare Intl-YWG Winnipeg
14h 55m1 stop Toronto Island
$388Multiple Airlines
Fri, Dec 11 - Sun, Dec 13
Multiple Airlines Logo
11:00 am - 12:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
25h 40m1 stop Toronto Pearson Intl
Multiple Airlines Logo
6:20 pm - 9:15 amORD  Chicago O'Hare Intl-YWG Winnipeg
14h 55m1 stop Toronto Island
$392Multiple Airlines
Sun, Feb 7 - Wed, Feb 10
Air Canada Logo
6:15 am - 4:38 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
10h 23m1 stop Toronto Pearson Intl
Air Canada Logo
8:40 pm - 10:24 amORD  Chicago O'Hare Intl-YWG Winnipeg
13h 44m1 stop Toronto Pearson Intl
$493Air Canada
Fri, Nov 20 - Fri, Nov 27
Air Canada Logo
6:15 am - 2:13 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
7h 58m1 stop Toronto Pearson Intl
Air Canada Logo
4:30 pm - 12:24 amORD  Chicago O'Hare Intl-YWG Winnipeg
7h 54m1 stop Toronto Pearson Intl
$543Air Canada
Thu, Jan 14 - Mon, Jan 18
Air Canada Logo
8:00 am - 10:45 amYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 45mnonstop
Air Canada Logo
6:17 pm - 12:24 amORD  Chicago O'Hare Intl-YWG Winnipeg
6h 07m1 stop Toronto Pearson Intl
$628Air Canada
Sun, Feb 7 - Wed, Feb 10
United Airlines Logo
3:15 pm - 6:02 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 47mnonstop
United Airlines Logo
10:00 am - 12:52 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 52mnonstop
$773United Airlines
Mon, Dec 21 - Sun, Dec 27
United Airlines Logo
3:15 pm - 6:02 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 47mnonstop
United Airlines Logo
2:47 pm - 8:57 pmORD  Chicago O'Hare Intl-YWG Winnipeg
6h 10m1 stop Denver Intl
$773United Airlines
Sun, Dec 20 - Fri, Dec 25
United Airlines Logo
3:15 pm - 6:02 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 47mnonstop
United Airlines Logo
10:00 am - 12:52 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 52mnonstop
$773United Airlines
Mon, Dec 21 - Fri, Dec 25

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American Airlines flights from Winnipeg to Chicago

Our best American Airlines deals on Winnipeg to Chicago flight tickets
American Airlines
Nov 25
YWG7:00 amWinnipeg
8h 36m
1 stop
ORD3:36 pmChicago O'Hare Intl
Dec 1
ORD2:50 pmChicago O'Hare Intl
7h 07m
1 stop
YWG9:57 pmWinnipeg
$455
American Airlines
Nov 25
YWG7:00 amWinnipeg
8h 36m
1 stop
ORD3:36 pmChicago O'Hare Intl
Dec 6
ORD2:50 pmChicago O'Hare Intl
7h 07m
1 stop
YWG9:57 pmWinnipeg
$547
American Airlines
Nov 27
YWG7:00 amWinnipeg
7h 10m
1 stop
ORD2:10 pmChicago O'Hare Intl
Nov 30
ORD2:50 pmChicago O'Hare Intl
7h 02m
1 stop
YWG9:52 pmWinnipeg
$548

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
Nov 3
YWG8:35 amWinnipeg
14h 30m
2 stops
ORD11:05 pmChicago O'Hare Intl
Nov 5
ORD6:20 amChicago O'Hare Intl
30h 30m
2 stops
YWG12:50 pmWinnipeg
$814
WestJet
Nov 3
YWG8:35 amWinnipeg
13h 30m
2 stops
ORD10:05 pmChicago O'Hare Intl
Nov 5
ORD6:20 amChicago O'Hare Intl
19h 24m
2 stops
YWG1:44 amWinnipeg
$839
WestJet
Oct 31
YWG6:00 amWinnipeg
11h 47m
2 stops
ORD5:47 pmChicago O'Hare Intl
Nov 6
ORD5:30 pmChicago O'Hare Intl
26h 15m
2 stops
YWG7:45 pmWinnipeg
$887

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

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Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 12/13

7:55 pm-6:40 pm

1 stop22h 45m

Chicago O'Hare Intl

Tue 12/15

6:20 pm-9:15 am

1 stop14h 55m

$377

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

7:55 pm-12:35 pm

1 stop16h 40m

Chicago O'Hare Intl

Wed 12/16

6:20 pm-9:15 am

1 stop14h 55m

$381

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 12/11

7:55 pm-12:35 pm

1 stop16h 40m

Chicago O'Hare Intl

Sun 12/13

6:20 pm-9:15 am

1 stop14h 55m

$388

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 2/7

11:00 am-12:40 pm

1 stop25h 40m

Chicago O'Hare Intl

Wed 2/10

6:20 pm-9:15 am

1 stop14h 55m

$392

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 11/20

6:15 am-4:38 pm

1 stop10h 23m

Chicago O'Hare Intl

Fri 11/27

8:40 pm-10:24 am

1 stop13h 44m

$493

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 1/14

6:15 am-2:13 pm

1 stop7h 58m

Chicago O'Hare Intl

Mon 1/18

4:30 pm-12:24 am

1 stop7h 54m

$543

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 2/7

8:00 am-10:45 am

Nonstop2h 45m

Chicago O'Hare Intl

Wed 2/10

6:17 pm-12:24 am

1 stop6h 07m

$628
Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/21

3:15 pm-6:02 pm

Nonstop2h 47m

Chicago O'Hare Intl

Sun 12/27

10:00 am-12:52 pm

Nonstop2h 52m

$773

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 12/20

3:15 pm-6:02 pm

Nonstop2h 47m

Chicago O'Hare Intl

Fri 12/25

2:47 pm-8:57 pm

1 stop6h 10m

$773

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/21

3:15 pm-6:02 pm

Nonstop2h 47m

Chicago O'Hare Intl

Fri 12/25

10:00 am-12:52 pm

Nonstop2h 52m

$773

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 typical for flights on this route.

Typical prices usually range from $325 to $493.
The lowest price recently found on this route was $377.

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 $505. If you’re not able to fly to Chicago in November, then January is your next best option. Flight prices from Winnipeg to Chicago during January average around $515.

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 $627. 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 $749.

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 $676. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $704.

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

2h 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 $377.
The fastest flight from Winnipeg to Chicago takes 2h 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 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?

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
7.3
10,415 reviews
Search United Airlines flights
Air CanadaPriceFrom $629Free CancellationRating
7.1
11,795 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 7 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 11,795 reviews) operates around 8 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 $629 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
Benton Harbor
Lansing
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