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

WestJet and Porter 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 October 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 52% of daily flights taking off in the afternoon.

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

As of October 2026, 50 flights take off from Winnipeg and land in Chicago each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

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 October 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.

$211 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

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:35 pm - 6:45 pmYWG Winnipeg-ORD Chicago O'Hare Intl

22h 10m2 stops Calgary Atlanta Hartsfield-Jackson

5:26 pm - 4:25 pmORD Chicago O'Hare Intl-YWG Winnipeg

22h 59m2 stops Atlanta Hartsfield-Jackson Calgary

$459Multiple Airlines

Wed, Nov 18 - Sat, Nov 21

11:00 am - 11:40 amYWG Winnipeg-ORD Chicago O'Hare Intl

24h 40m1 stop Toronto Pearson Intl

8:15 am - 1:10 amORD Chicago O'Hare Intl-YWG Winnipeg

16h 55m2 stops Atlanta Hartsfield-Jackson Calgary

$493Multiple Airlines

Thu, Dec 3 - Sun, Dec 6

11:00 am - 11:40 amYWG Winnipeg-ORD Chicago O'Hare Intl

24h 40m1 stop Toronto Pearson Intl

6:20 pm - 10:15 amORD Chicago O'Hare Intl-YWG Winnipeg

15h 55m1 stop Toronto Island

$500Multiple Airlines

Thu, Dec 3 - Sun, Dec 6

6:55 pm - 11:40 amYWG Winnipeg-ORD Chicago O'Hare Intl

16h 45m1 stop Toronto Pearson Intl

6:20 pm - 10:15 amORD Chicago O'Hare Intl-YWG Winnipeg

15h 55m1 stop Toronto Island

$502Multiple Airlines

Fri, Oct 30 - Sun, Nov 1

11:00 am - 11:40 amYWG Winnipeg-ORD Chicago O'Hare Intl

24h 40m1 stop Toronto Pearson Intl

8:15 am - 12:10 amORD Chicago O'Hare Intl-YWG Winnipeg

15h 55m2 stops Atlanta Hartsfield-Jackson Calgary

$503Multiple Airlines

Thu, Dec 3 - Sun, Dec 6

11:00 am - 11:40 amYWG Winnipeg-ORD Chicago O'Hare Intl

24h 40m1 stop Toronto Pearson Intl

6:20 pm - 10:15 amORD Chicago O'Hare Intl-YWG Winnipeg

15h 55m1 stop Toronto Island

$504Multiple Airlines

Fri, Nov 20 - Sat, Nov 21

9:35 pm - 12:51 pmYWG Winnipeg-ORD Chicago O'Hare Intl

15h 16m2 stops Calgary Atlanta Hartsfield-Jackson

6:00 am - 12:10 amORD Chicago O'Hare Intl-YWG Winnipeg

18h 10m3 stops Baltimore/Washington Atlanta Hartsfield-Jackson Calgary

$504Multiple Airlines

Fri, Oct 30 - Fri, Nov 6

6:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

10h 40m1 stop Calgary

7:50 pm - 1:10 amORD Chicago O'Hare Intl-YWG Winnipeg

29h 20m2 stops Atlanta Hartsfield-Jackson Calgary

$507Multiple Airlines

Thu, Oct 22 - Tue, Oct 27

2:15 pm - 5:02 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 47mnonstop

6:50 am - 8:57 pmORD Chicago O'Hare Intl-YWG Winnipeg

14h 07m1 stop Denver Intl

$735United Airlines

Fri, Dec 18 - Sun, Jan 3

7:00 am - 9:31 amYWG Winnipeg-ORD Chicago O'Hare Intl

2h 31mnonstop

7:15 am - 8:55 pmORD Chicago O'Hare Intl-YWG Winnipeg

13h 40m1 stop Denver Intl

$735United Airlines

Thu, Feb 25 - Sun, Feb 28

Cheap last minute flights

Enter your travel dates to find the best prices.

2:00 pm - 4:35 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

1:55 pm - 8:00 pmORD Chicago O'Hare Intl-YWG Winnipeg

6h 05m1 stop Ottawa

$798Air Canada

Wed, Oct 7 - Wed, Oct 14

2:00 pm - 4:35 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

7:54 pm - 10:33 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mnonstop

$798Air Canada

Wed, Oct 7 - Wed, Oct 14

10:50 am - 8:12 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 22m1 stop Montreal Pierre Elliott Trudeau Intl

1:55 pm - 8:00 pmORD Chicago O'Hare Intl-YWG Winnipeg

6h 05m1 stop Ottawa

$801Air Canada

Wed, Oct 7 - Wed, Oct 14

8:50 pm - 2:20 pmYWG Winnipeg-ORD Chicago O'Hare Intl

17h 30m1 stop Toronto Pearson Intl

9:46 am - 10:43 amORD Chicago O'Hare Intl-YWG Winnipeg

24h 57m2 stops Toronto Pearson Intl Ottawa

$839Porter Airlines

Wed, Oct 7 - Wed, Oct 14

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

9h 40m2 stops Calgary Minneapolis St Paul

7:35 am - 8:00 pmORD Chicago O'Hare Intl-YWG Winnipeg

12h 25m2 stops Salt Lake City Vancouver Intl

$851WestJet

Wed, Oct 7 - Wed, Oct 14

5:40 pm - 9:27 pmYWG Winnipeg-ORD Chicago O'Hare Intl

3h 47m1 stop Minneapolis St Paul

7:49 pm - 12:10 amORD Chicago O'Hare Intl-YWG Winnipeg

28h 21m2 stops Atlanta Hartsfield-Jackson Calgary

$852Multiple Airlines

Thu, Oct 8 - Fri, Nov 6

7:20 am - 5:05 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 45m1 stop Calgary

8:40 pm - 11:24 amORD Chicago O'Hare Intl-YWG Winnipeg

14h 44m1 stop Toronto Pearson Intl

$860Air Canada

Thu, Oct 8 - Fri, Nov 6

2:00 pm - 4:35 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

8:40 pm - 11:24 amORD Chicago O'Hare Intl-YWG Winnipeg

14h 44m1 stop Toronto Pearson Intl

$860Air Canada

Thu, Oct 8 - Fri, Nov 6

2:00 pm - 4:35 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

9:35 am - 12:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$957United Airlines

Thu, Oct 8 - Fri, Nov 6

8:45 am - 11:59 pmYWG Winnipeg-ORD Chicago O'Hare Intl

15h 14m1 stop Denver Intl

10:00 am - 12:37 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mnonstop

$1,104United Airlines

Wed, Oct 7 - Thu, Oct 8

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Delta flights from Winnipeg to Chicago

Our best Delta deals on Winnipeg to Chicago flight tickets

Delta

Feb 25

YWG6:35 amWinnipeg

11h 57m

2 stops

ORD6:32 pmChicago O'Hare Intl

Feb 28

ORD6:00 amChicago O'Hare Intl

5h 50m

1 stop

YWG11:50 amWinnipeg

$601

Delta

Oct 13

YWG5:40 pmWinnipeg

3h 47m

1 stop

ORD9:27 pmChicago O'Hare Intl

Oct 18

ORD6:20 amChicago O'Hare Intl

5h 28m

1 stop

YWG11:48 amWinnipeg

$803

Delta

Oct 13

YWG12:38 pmWinnipeg

11h 19m

2 stops

ORD11:57 pmChicago O'Hare Intl

Oct 18

ORD6:20 amChicago O'Hare Intl

5h 28m

1 stop

YWG11:48 amWinnipeg

$866

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

Oct 22

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

Oct 23

ORD5:30 pmChicago O'Hare Intl

22h 30m

2 stops

YWG4:00 pmWinnipeg

$534

WestJet

Oct 21

YWG9:05 pmWinnipeg

19h 35m

1 stop

ORD4:40 pmChicago O'Hare Intl

Oct 23

ORD5:30 pmChicago O'Hare Intl

15h 50m

2 stops

YWG9:20 amWinnipeg

$580

WestJet

Oct 22

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

Oct 23

ORD5:30 pmChicago O'Hare Intl

26h 45m

1 stop

YWG8:15 pmWinnipeg

$598

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 11/18

8:35 pm-6:45 pm

2 stops22h 10m

Chicago O'Hare Intl

Sat 11/21

5:26 pm-4:25 pm

2 stops22h 59m

$459

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/3

11:00 am-11:40 am

1 stop24h 40m

Chicago O'Hare Intl

Sun 12/6

8:15 am-1:10 am

2 stops16h 55m

$493

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/3

11:00 am-11:40 am

1 stop24h 40m

Chicago O'Hare Intl

Sun 12/6

6:20 pm-10:15 am

1 stop15h 55m

$500

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 10/30

6:55 pm-11:40 am

1 stop16h 45m

Chicago O'Hare Intl

Sun 11/1

6:20 pm-10:15 am

1 stop15h 55m

$502

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/3

11:00 am-11:40 am

1 stop24h 40m

Chicago O'Hare Intl

Sun 12/6

8:15 am-12:10 am

2 stops15h 55m

$503

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 11/20

11:00 am-11:40 am

1 stop24h 40m

Chicago O'Hare Intl

Sat 11/21

6:20 pm-10:15 am

1 stop15h 55m

$504

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 10/30

9:35 pm-12:51 pm

2 stops15h 16m

Chicago O'Hare Intl

Fri 11/6

6:00 am-12:10 am

3 stops18h 10m

$504

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 10/22

6:00 am-4:40 pm

1 stop10h 40m

Chicago O'Hare Intl

Tue 10/27

7:50 pm-1:10 am

2 stops29h 20m

$507

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 12/18

2:15 pm-5:02 pm

Nonstop2h 47m

Chicago O'Hare Intl

Sun 1/3

6:50 am-8:57 pm

1 stop14h 07m

$735

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 2/25

7:00 am-9:31 am

Nonstop2h 31m

Chicago O'Hare Intl

Sun 2/28

7:15 am-8:55 pm

1 stop13h 40m

$735

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 $474 to $629.
The lowest price recently found on this route was $459.

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 $609. 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 $781.

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 $668. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $682.

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	$211
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 $211. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $459.

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 1 as of October 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 84.87% of the total bookings. Other popular models include Boeing 737-700 Passenger/BBJ1 (winglets) with 6.72%, Boeing 737 MAX 8 with 3.36%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 1.68%.
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 $517	Free Cancellation	Rating 7.4 10,285 reviews		Search United Airlines flights

United Airlines Flights From Winnipeg to Chicago
United Airlines flight deals from Winnipeg to Chicago start from $517 round-trip. Over the 11 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.

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Saint Joseph

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.

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Wed 11/4

Wed 11/11

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Winnipeg

Complete your trip

Feeling lucky

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 $211

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 11/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Delta flights from Winnipeg to Chicago

Our best Delta deals on Winnipeg to Chicago flight tickets

WestJet flights from Winnipeg to Chicago

Our best WestJet 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 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

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year