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

Porter Airlines is the most popular carrier operating from Winnipeg to Chicago

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

As of September 2026, 52 flights take off from Winnipeg and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.

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

As of September 2026, 7 flights take off from Winnipeg and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 51% of daily flights taking off in the afternoon.

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?

The number of operators available for flights from Winnipeg Airport to Chicago is 1 as of September 2026.

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.

$173 Cheap Flights from Winnipeg to Chicago in 2026

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Find the cheapest flights from Winnipeg to Chicago

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7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

5:30 pm - 11:10 amORD Chicago O'Hare Intl-YWG Winnipeg

17h 40m1 stop Calgary

$338WestJet

Sun, Oct 18 - Mon, Oct 19

7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

6:20 pm - 6:10 pmORD Chicago O'Hare Intl-YWG Winnipeg

23h 50m2 stops Toronto Island Ottawa

$344Multiple Airlines

Fri, Oct 23 - Tue, Oct 27

7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

6:20 pm - 9:15 amORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

$349Multiple Airlines

Fri, Oct 23 - Tue, Oct 27

4:15 pm - 11:40 amYWG Winnipeg-ORD Chicago O'Hare Intl

19h 25m2 stops Ottawa Toronto Pearson Intl

6:20 pm - 9:15 amORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

$350Multiple Airlines

Sat, Oct 24 - Sun, Oct 25

4:55 pm - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

23h 45m1 stop Calgary

5:30 pm - 12:55 amORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

$350WestJet

Wed, Oct 21 - Fri, Oct 23

9:20 am - 11:40 amYWG Winnipeg-ORD Chicago O'Hare Intl

26h 20m1 stop Toronto Pearson Intl

6:20 pm - 10:45 amORD Chicago O'Hare Intl-YWG Winnipeg

16h 25m1 stop Toronto Island

$364Porter Airlines

Sat, Oct 24 - Sun, Oct 25

7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

5:30 pm - 9:35 amORD Chicago O'Hare Intl-YWG Winnipeg

16h 05m2 stops Calgary Saskatoon

$366WestJet

Sun, Oct 18 - Mon, Oct 19

2:55 pm - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

25h 45m1 stop Calgary

5:30 pm - 11:10 amORD Chicago O'Hare Intl-YWG Winnipeg

17h 40m1 stop Calgary

$369WestJet

Sat, Oct 17 - Mon, Oct 19

7:15 am - 8:00 amYWG Winnipeg-ORD Chicago O'Hare Intl

24h 45m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

7:00 am - 11:44 pmORD Chicago O'Hare Intl-YWG Winnipeg

16h 44m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

$684United Airlines

Sun, Nov 15 - Tue, Dec 15

2:15 pm - 4:50 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

10:00 am - 12:52 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 52mnonstop

$741United Airlines

Fri, Nov 13 - Fri, Dec 18

Cheap last minute flights

Enter your travel dates to find the best prices.

8:10 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

18h 25m1 stop Toronto Pearson Intl

3:20 pm - 9:45 amMDW Chicago Midway-YWG Winnipeg

18h 25m1 stop Toronto Island

$642Multiple Airlines

Fri, Sep 18 - Sun, Sep 20

8:10 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

14h 50m1 stop Toronto Pearson Intl

3:20 pm - 10:43 amMDW Chicago Midway-YWG Winnipeg

19h 23m2 stops Toronto Island Ottawa

$658Multiple Airlines

Fri, Sep 18 - Sun, Sep 20

5:10 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

17h 50m1 stop Toronto Pearson Intl

3:20 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

$695Multiple Airlines

Thu, Sep 17 - Sat, Sep 19

9:05 pm - 5:51 pmYWG Winnipeg-MDW Chicago Midway

20h 46m2 stops Calgary Atlanta Hartsfield-Jackson

3:20 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

$754Multiple Airlines

Thu, Sep 17 - Sat, Sep 19

8:45 pm - 4:18 pmYWG Winnipeg-ORD Chicago O'Hare Intl

19h 33m1 stop Toronto Pearson Intl

8:03 am - 3:19 pmORD Chicago O'Hare Intl-YWG Winnipeg

7h 16m1 stop Toronto Pearson Intl

$760Porter Airlines

Fri, Sep 18 - Sun, Sep 20

5:10 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

17h 50m1 stop Toronto Pearson Intl

3:20 pm - 12:55 amMDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

$762Multiple Airlines

Thu, Sep 17 - Mon, Sep 21

5:10 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

17h 50m1 stop Toronto Pearson Intl

3:20 pm - 12:55 amMDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

$768Multiple Airlines

Thu, Sep 17 - Mon, Sep 21

5:10 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

17h 50m1 stop Toronto Pearson Intl

3:20 pm - 12:00 pmMDW Chicago Midway-YWG Winnipeg

20h 40m2 stops Toronto Island Edmonton

$792Multiple Airlines

Thu, Sep 17 - Mon, Sep 21

5:10 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

17h 50m1 stop Toronto Pearson Intl

3:20 pm - 12:00 pmMDW Chicago Midway-YWG Winnipeg

20h 40m2 stops Toronto Island Edmonton

$799Multiple Airlines

Thu, Sep 17 - Mon, Sep 21

7:00 am - 9:35 amYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

7:00 am - 8:57 pmORD Chicago O'Hare Intl-YWG Winnipeg

13h 57m1 stop Denver Intl

$1,131United Airlines

Thu, Sep 17 - Fri, Sep 18

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WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

Oct 18

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

Oct 19

ORD5:30 pmChicago O'Hare Intl

17h 40m

1 stop

YWG11:10 amWinnipeg

$338

WestJet

Oct 21

YWG4:55 pmWinnipeg

23h 45m

1 stop

ORD4:40 pmChicago O'Hare Intl

Oct 23

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

$350

WestJet

Oct 18

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

Oct 19

ORD5:30 pmChicago O'Hare Intl

16h 05m

2 stops

YWG9:35 amWinnipeg

$366

Air Canada flights from Winnipeg to Chicago

Our best Air Canada deals on Winnipeg to Chicago flight tickets

Air Canada

Oct 13

YWG5:00 amWinnipeg

8h 23m

1 stop

ORD1:23 pmChicago O'Hare Intl

Oct 20

ORD3:45 pmChicago O'Hare Intl

8h 02m

1 stop

YWG11:47 pmWinnipeg

$479

Air Canada

Oct 18

YWG5:00 amWinnipeg

8h 23m

1 stop

ORD1:23 pmChicago O'Hare Intl

Oct 20

ORD9:55 amChicago O'Hare Intl

8h 17m

1 stop

YWG6:12 pmWinnipeg

$480

Air Canada

Sep 28

YWG7:10 pmWinnipeg

12h 50m

1 stop

ORD8:00 amChicago O'Hare Intl

Oct 10

ORD9:55 amChicago O'Hare Intl

6h 32m

1 stop

YWG4:27 pmWinnipeg

$611

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 10/18

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 10/19

5:30 pm-11:10 am

1 stop17h 40m

$338

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 10/23

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 10/27

6:20 pm-6:10 pm

2 stops23h 50m

$344

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 10/23

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 10/27

6:20 pm-9:15 am

1 stop14h 55m

$349

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 10/24

4:15 pm-11:40 am

2 stops19h 25m

Chicago O'Hare Intl

Sun 10/25

6:20 pm-9:15 am

1 stop14h 55m

$350

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 10/21

4:55 pm-4:40 pm

1 stop23h 45m

Chicago O'Hare Intl

Fri 10/23

5:30 pm-12:55 am

1 stop7h 25m

$350

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 10/24

9:20 am-11:40 am

1 stop26h 20m

Chicago O'Hare Intl

Sun 10/25

6:20 pm-10:45 am

1 stop16h 25m

$364

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 10/18

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 10/19

5:30 pm-9:35 am

2 stops16h 05m

$366

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 10/17

2:55 pm-4:40 pm

1 stop25h 45m

Chicago O'Hare Intl

Mon 10/19

5:30 pm-11:10 am

1 stop17h 40m

$369

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 11/15

7:15 am-8:00 am

2 stops24h 45m

Chicago O'Hare Intl

Tue 12/15

7:00 am-11:44 pm

2 stops16h 44m

$684

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 11/13

2:15 pm-4:50 pm

Nonstop2h 35m

Chicago O'Hare Intl

Fri 12/18

10:00 am-12:52 pm

Nonstop2h 52m

$741

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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 $388 to $663.
The lowest price recently found on this route was $338.

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 $487. 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 $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 $602. 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 $793.

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 $671. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $680.

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 57% 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 September 2026, prices for Winnipeg to Chicago flights are approximately 9% cheaper 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	$173
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 $173. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $338.

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?
The number of operators available for flights from Winnipeg Airport to Chicago is 1 as of September 2026.
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?
Based on momondo bookings for flights between Winnipeg and Chicago, the leading plane model is Embraer 175 (Enhanced Winglets), making up 86.67% of the total bookings. Other popular models include Boeing 737-700 Passenger/BBJ1 (winglets) with 5.93%, Boeing 737 MAX 8 with 2.96%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 1.48%.
What is the most popular airline from Winnipeg to Chicago?
Based on momondo bookings for flights between Winnipeg and Chicago, the leading airline is United Airlines, making up 100% of the total bookings.

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 Airlines	PriceFrom $471	Free Cancellation	Rating 7.4 10,213 reviews		Search United Airlines flights

United Airlines Flights From Winnipeg to Chicago
United Airlines flight deals from Winnipeg to Chicago start from $471 round-trip. Over the 12 United Airlines flights for this route in a normal week, average airfare is usually $701 round-trip - but some users have found much cheaper deals with momondo.

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Porter

Crown Point

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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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Winnipeg to Chicago from $173

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 10/18. 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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WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

Air Canada flights from Winnipeg to Chicago

Our best Air Canada deals on Winnipeg to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Winnipeg to Chicago

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

What is the cheapest month to fly to Chicago?

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

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

What is the cheapest Winnipeg to Chicago flight route?

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

Can stopping save me money on Winnipeg to Chicago flights?

How have Winnipeg to Chicago flight prices changed over time?

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

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

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

When to book flights from Winnipeg to Chicago

Cheap Winnipeg to Chicago (YWG to CHI) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Winnipeg

According to popular flight searches on momondo this year

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