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

As of November 2026, 28 flights take off from Winnipeg and land in Chicago each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.

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

Porter Airlines, WestJet, and United Airlines are the most popular carriers operating from Winnipeg to Chicago

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

As of November 2026, 4 flights take off from Winnipeg and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 50% of daily flights taking off at noon.

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 2 as of November 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.

$201 Cheap Flights from Winnipeg to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Chicago

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Cheap round-trip flights

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9:35 pm - 2:30 pmYWG Winnipeg-ORD Chicago O'Hare Intl

17h 55m2 stops Calgary Atlanta Hartsfield-Jackson

8:30 am - 1:10 amORD Chicago O'Hare Intl-YWG Winnipeg

15h 40m2 stops Atlanta Hartsfield-Jackson Calgary

$407Multiple Airlines

Mon, Dec 14 - Wed, Dec 16

9:35 pm - 2:30 pmYWG Winnipeg-ORD Chicago O'Hare Intl

17h 55m2 stops Calgary Atlanta Hartsfield-Jackson

10:29 pm - 5:25 pmORD Chicago O'Hare Intl-YWG Winnipeg

17h 56m2 stops Atlanta Hartsfield-Jackson Calgary

$431Multiple Airlines

Fri, Dec 4 - Mon, Dec 7

7:55 pm - 11:34 amYWG Winnipeg-ORD Chicago O'Hare Intl

16h 39m1 stop Toronto Pearson Intl

8:30 am - 1:10 amORD Chicago O'Hare Intl-YWG Winnipeg

15h 40m2 stops Atlanta Hartsfield-Jackson Calgary

$437Multiple Airlines

Mon, Dec 14 - Wed, Dec 16

9:35 pm - 2:30 pmYWG Winnipeg-ORD Chicago O'Hare Intl

17h 55m2 stops Calgary Atlanta Hartsfield-Jackson

5:58 am - 2:40 pmORD Chicago O'Hare Intl-YWG Winnipeg

7h 42m1 stop Atlanta Hartsfield-Jackson

$438Multiple Airlines

Mon, Dec 14 - Mon, Dec 21

3:15 pm - 5:02 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 47mnonstop

10:00 am - 1:52 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 52mnonstop

$679United Airlines

Thu, Dec 17 - Sun, Dec 20

3:15 pm - 5:00 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mnonstop

10:55 am - 9:55 pmORD Chicago O'Hare Intl-YWG Winnipeg

10h 00m1 stop Denver Intl

$680United Airlines

Thu, Dec 3 - Sun, Dec 6

8:00 am - 9:45 amYWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mnonstop

2:24 pm - 9:55 pmORD Chicago O'Hare Intl-YWG Winnipeg

6h 31m1 stop Denver Intl

$680United Airlines

Sun, Feb 7 - Wed, Feb 10

6:15 am - 3:02 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 47m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

7:05 am - 10:24 pmORD Chicago O'Hare Intl-YWG Winnipeg

14h 19m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

$703Air Canada

Thu, Dec 3 - Sun, Dec 6

6:15 am - 11:57 amYWG Winnipeg-ORD Chicago O'Hare Intl

6h 42m1 stop Toronto Pearson Intl

3:45 pm - 1:24 amORD Chicago O'Hare Intl-YWG Winnipeg

8h 39m1 stop Toronto Pearson Intl

$732Air Canada

Thu, Dec 10 - Tue, Jan 5

6:15 am - 11:57 amYWG Winnipeg-ORD Chicago O'Hare Intl

6h 42m1 stop Toronto Pearson Intl

7:01 am - 3:09 pmORD Chicago O'Hare Intl-YWG Winnipeg

7h 08m1 stop Toronto Pearson Intl

$732Air Canada

Thu, Dec 10 - Thu, Jan 7

Cheap last minute flights

Enter your travel dates to find the best prices.

6:00 am - 5:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

12h 40m1 stop Toronto Pearson Intl

6:20 pm - 7:14 pmORD Chicago O'Hare Intl-YWG Winnipeg

23h 54m2 stops Toronto Island Ottawa

$684Multiple Airlines

Tue, Nov 3 - Mon, Nov 30

9:05 pm - 11:34 amYWG Winnipeg-ORD Chicago O'Hare Intl

15h 29m1 stop Toronto Pearson Intl

6:20 pm - 7:14 pmORD Chicago O'Hare Intl-YWG Winnipeg

23h 54m2 stops Toronto Island Ottawa

$695Multiple Airlines

Sun, Nov 8 - Mon, Nov 30

6:00 am - 5:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

12h 40m1 stop Toronto Pearson Intl

6:20 pm - 12:05 pmORD Chicago O'Hare Intl-YWG Winnipeg

16h 45m1 stop Toronto Island

$698Multiple Airlines

Tue, Nov 3 - Mon, Nov 30

9:05 pm - 11:34 amYWG Winnipeg-ORD Chicago O'Hare Intl

15h 29m1 stop Toronto Pearson Intl

6:20 pm - 11:47 amORD Chicago O'Hare Intl-YWG Winnipeg

16h 27m1 stop Toronto Island

$709Multiple Airlines

Sun, Nov 8 - Mon, Nov 30

6:15 am - 11:57 amYWG Winnipeg-ORD Chicago O'Hare Intl

6h 42m1 stop Toronto Pearson Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$1,037United Airlines

Tue, Nov 3 - Mon, Nov 30

6:15 am - 3:38 pmYWG Winnipeg-ORD Chicago O'Hare Intl

10h 23m1 stop Toronto Pearson Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$1,097Air Canada

Wed, Nov 4 - Mon, Nov 30

12:20 pm - 7:05 pmYWG Winnipeg-ORD Chicago O'Hare Intl

7h 45m1 stop Toronto Pearson Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$1,100Air Canada

Wed, Nov 4 - Fri, Nov 6

6:15 am - 6:30 pmYWG Winnipeg-ORD Chicago O'Hare Intl

13h 15m2 stops Toronto Pearson Intl Ottawa

1:55 pm - 12:44 amORD Chicago O'Hare Intl-YWG Winnipeg

9h 49m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

$1,123Air Canada

Tue, Nov 3 - Mon, Nov 30

9:40 am - 6:38 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 58m1 stop Denver Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$1,248United Airlines

Sat, Nov 7 - Mon, Nov 30

12:20 pm - 7:58 pmYWG Winnipeg-ORD Chicago O'Hare Intl

8h 38m1 stop Toronto Pearson Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$1,798United Airlines

Fri, Nov 6 - Fri, Nov 13

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WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

Apr 26

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

May 3

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

$464

WestJet

Apr 26

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

May 3

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

$507

WestJet

Dec 1

YWG6:00 amWinnipeg

13h 01m

2 stops

MDW6:01 pmChicago Midway

Dec 2

MDW12:39 pmChicago Midway

21h 52m

1 stop

YWG11:31 amWinnipeg

$603

Delta flights from Winnipeg to Chicago

Our best Delta deals on Winnipeg to Chicago flight tickets

Delta

Dec 6

YWG5:45 pmWinnipeg

21h 11m

2 stops

ORD1:56 pmChicago O'Hare Intl

Jan 4

ORD5:18 pmChicago O'Hare Intl

17h 16m

2 stops

YWG11:34 amWinnipeg

$565

Delta

Jan 26

YWG7:15 amWinnipeg

11h 45m

2 stops

MDW6:00 pmChicago Midway

Jan 27

MDW6:40 pmChicago Midway

15h 54m

2 stops

YWG11:34 amWinnipeg

$613

Delta

Jan 26

YWG7:15 amWinnipeg

11h 45m

2 stops

MDW6:00 pmChicago Midway

Jan 27

MDW6:40 pmChicago Midway

15h 54m

2 stops

YWG11:34 amWinnipeg

$614

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

9:35 pm-2:30 pm

2 stops17h 55m

Chicago O'Hare Intl

Wed 12/16

8:30 am-1:10 am

2 stops15h 40m

$407

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 12/4

9:35 pm-2:30 pm

2 stops17h 55m

Chicago O'Hare Intl

Mon 12/7

10:29 pm-5:25 pm

2 stops17h 56m

$431

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

7:55 pm-11:34 am

1 stop16h 39m

Chicago O'Hare Intl

Wed 12/16

8:30 am-1:10 am

2 stops15h 40m

$437

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

9:35 pm-2:30 pm

2 stops17h 55m

Chicago O'Hare Intl

Mon 12/21

5:58 am-2:40 pm

1 stop7h 42m

$438

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/17

3:15 pm-5:02 pm

Nonstop2h 47m

Chicago O'Hare Intl

Sun 12/20

10:00 am-1:52 pm

Nonstop2h 52m

$679

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/3

3:15 pm-5:00 pm

Nonstop2h 45m

Chicago O'Hare Intl

Sun 12/6

10:55 am-9:55 pm

1 stop10h 00m

$680

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 2/7

8:00 am-9:45 am

Nonstop2h 45m

Chicago O'Hare Intl

Wed 2/10

2:24 pm-9:55 pm

1 stop6h 31m

$680

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/3

6:15 am-3:02 pm

2 stops9h 47m

Chicago O'Hare Intl

Sun 12/6

7:05 am-10:24 pm

2 stops14h 19m

$703

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/10

6:15 am-11:57 am

1 stop6h 42m

Chicago O'Hare Intl

Tue 1/5

3:45 pm-1:24 am

1 stop8h 39m

$732

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/10

6:15 am-11:57 am

1 stop6h 42m

Chicago O'Hare Intl

Thu 1/7

7:01 am-3:09 pm

1 stop7h 08m

$732

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 cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Winnipeg, with most prices found around $523. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Winnipeg to Chicago during May average around $542.

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 $619. This is often the case because there is less demand to fly during this day of the week. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago for around $718.

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 $673. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $697.

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 42% 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 2026, prices for Winnipeg to Chicago flights are approximately 59% 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	$201
Fastest flight time	2h 21m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Winnipeg in the past 72 hours is $201. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $407.

The fastest flight from Winnipeg to Chicago takes 2h 21m

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 21m.
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 2 as of November 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 82.96% of the total bookings. Other popular models include Boeing 737 MAX 8 with 5.93%, Boeing 737-700 Passenger/BBJ1 (winglets) with 5.93%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 2.22%.

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 $517	Free Cancellation	Rating 7.3 10,464 reviews		Search United Airlines flights
Air Canada	PriceFrom $629	Free Cancellation	Rating 7.1 11,844 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 11,844 reviews) operates around 7 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.

Merrillville

New Buffalo

Hammond

Portage

Lansing

Saint Joseph

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.

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 $201

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 11/30. 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

Delta flights from Winnipeg to Chicago

Our best Delta deals on Winnipeg to Chicago flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Winnipeg to 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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