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

As of August 2026, 7 flights take off from Winnipeg and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 59% of daily flights taking off at noon.

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

As of August 2026, 51 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.

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

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

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 August 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.

$164 Cheap Flights from Winnipeg to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Chicago

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One-way

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Enter your travel dates to find the best prices.

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

9h 40m1 stop Calgary

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

7h 25m1 stop Calgary

$288WestJet

Tue, Sep 8 - Thu, Sep 10

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

9h 40m1 stop Calgary

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

7h 25m1 stop Calgary

$300WestJet

Thu, Oct 22 - Fri, Oct 23

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

9h 40m1 stop Calgary

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

7h 25m1 stop Calgary

$311WestJet

Tue, Sep 8 - Fri, Sep 11

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

9h 40m1 stop Calgary

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

7h 25m1 stop Calgary

$311WestJet

Tue, Sep 8 - Tue, Sep 15

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

$321WestJet

Thu, Oct 1 - Sun, Oct 4

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

9h 40m1 stop Calgary

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

7h 25m1 stop Calgary

$322WestJet

Tue, Sep 8 - Sun, Sep 13

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

25h 45m1 stop Calgary

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

7h 25m1 stop Calgary

$322WestJet

Thu, Sep 10 - Sun, Sep 13

7:10 pm - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

21h 30m1 stop Calgary

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

7h 25m1 stop Calgary

$329WestJet

Sat, Sep 19 - Mon, Sep 21

8:15 am - 5:55 amYWG Winnipeg-ORD Chicago O'Hare Intl

21h 40m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

9:25 pm - 4:27 pmORD Chicago O'Hare Intl-YWG Winnipeg

19h 02m2 stops Nashville Intl Toronto Pearson Intl

$648United Airlines

Tue, Sep 22 - Tue, Sep 29

5:00 am - 8:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

15h 40m2 stops Toronto Pearson Intl Boston Logan Intl

6:55 am - 9:27 pmORD Chicago O'Hare Intl-YWG Winnipeg

14h 32m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

$655United Airlines

Wed, Sep 23 - Sat, Sep 26

Cheap last minute flights

Enter your travel dates to find the best prices.

12:15 pm - 8:20 pmYWG Winnipeg-ORD Chicago O'Hare Intl

8h 05m1 stop Toronto Pearson Intl

8:32 pm - 5:58 pmORD Chicago O'Hare Intl-YWG Winnipeg

21h 26m2 stops Toronto Pearson Intl Ottawa

$693Porter Airlines

Wed, Sep 2 - Sat, Sep 5

5:42 pm - 9:47 pmYWG Winnipeg-ORD Chicago O'Hare Intl

4h 05m1 stop Minneapolis St Paul

6:20 am - 11:40 pmORD Chicago O'Hare Intl-YWG Winnipeg

17h 20m2 stops Atlanta Hartsfield-Jackson Calgary

$709Multiple Airlines

Wed, Sep 2 - Wed, Sep 9

7:45 am - 8:20 pmYWG Winnipeg-ORD Chicago O'Hare Intl

12h 35m1 stop Toronto Pearson Intl

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

12h 25m3 stops Quincy Regional Nashville Intl Toronto Pearson Intl

$714Multiple Airlines

Wed, Sep 2 - Wed, Sep 9

11:15 am - 8:20 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 05m2 stops Montreal St Hubert Toronto Pearson Intl

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

12h 25m3 stops Quincy Regional Nashville Intl Toronto Pearson Intl

$734Multiple Airlines

Wed, Sep 2 - Wed, Sep 9

7:45 am - 5:52 amYWG Winnipeg-ORD Chicago O'Hare Intl

22h 07m3 stops Toronto Pearson Intl Cancun Mexico City Benito Juarez

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

12h 25m3 stops Quincy Regional Nashville Intl Toronto Pearson Intl

$778Multiple Airlines

Wed, Sep 2 - Wed, Sep 9

6:15 am - 5:52 amYWG Winnipeg-ORD Chicago O'Hare Intl

23h 37m3 stops Toronto Pearson Intl Cancun Mexico City Benito Juarez

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

12h 25m3 stops Quincy Regional Nashville Intl Toronto Pearson Intl

$782Multiple Airlines

Wed, Sep 2 - Wed, Sep 9

9:05 pm - 9:59 amYWG Winnipeg-MDW Chicago Midway

12h 54m2 stops Calgary Atlanta Hartsfield-Jackson

9:59 am - 3:08 pmMDW Chicago Midway-YWG Winnipeg

5h 09m1 stop Minneapolis St Paul

$783WestJet

Wed, Sep 2 - Wed, Sep 9

3:58 pm - 9:47 pmYWG Winnipeg-ORD Chicago O'Hare Intl

5h 49m1 stop Minneapolis St Paul

8:25 am - 3:08 pmORD Chicago O'Hare Intl-YWG Winnipeg

6h 43m1 stop Minneapolis St Paul

$784WestJet

Wed, Sep 2 - Wed, Sep 9

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

2h 35mnonstop

9:00 am - 11:20 pmORD Chicago O'Hare Intl-YWG Winnipeg

14h 20m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

$930United Airlines

Sun, Aug 30 - Sun, Sep 6

8:45 am - 10:00 pmYWG Winnipeg-ORD Chicago O'Hare Intl

13h 15m1 stop Denver Intl

9:00 am - 11:20 pmORD Chicago O'Hare Intl-YWG Winnipeg

14h 20m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

$936United Airlines

Sun, Aug 30 - Sun, Sep 6

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WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

Sep 8

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

Sep 10

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

$288

WestJet

Oct 22

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

Oct 23

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

$300

WestJet

Sep 8

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

Sep 11

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

$311

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets

Porter Airlines

Sep 24

YWG8:45 pmWinnipeg

14h 15m

1 stop

MDW11:00 amChicago Midway

Sep 27

MDW3:20 pmChicago Midway

19h 23m

2 stops

YWG10:43 amWinnipeg

$540

Porter Airlines

Sep 9

YWG9:20 amWinnipeg

6h 58m

1 stop

ORD4:18 pmChicago O'Hare Intl

Sep 12

ORD8:03 amChicago O'Hare Intl

7h 16m

1 stop

YWG3:19 pmWinnipeg

$610

Porter Airlines

Sep 26

YWG11:15 amWinnipeg

23h 45m

2 stops

MDW11:00 amChicago Midway

Oct 3

MDW3:20 pmChicago Midway

26h 38m

2 stops

YWG5:58 pmWinnipeg

$650

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 9/8

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 9/10

5:30 pm-12:55 am

1 stop7h 25m

$288

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 10/22

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 10/23

5:30 pm-12:55 am

1 stop7h 25m

$300

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 9/8

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 9/11

5:30 pm-12:55 am

1 stop7h 25m

$311

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 9/8

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 9/15

5:30 pm-12:55 am

1 stop7h 25m

$311

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 10/1

4:55 pm-4:40 pm

1 stop23h 45m

Chicago O'Hare Intl

Sun 10/4

5:30 pm-12:55 am

1 stop7h 25m

$321

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 9/8

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 9/13

5:30 pm-12:55 am

1 stop7h 25m

$322

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 9/10

2:55 pm-4:40 pm

1 stop25h 45m

Chicago O'Hare Intl

Sun 9/13

5:30 pm-12:55 am

1 stop7h 25m

$322

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 9/19

7:10 pm-4:40 pm

1 stop21h 30m

Chicago O'Hare Intl

Mon 9/21

5:30 pm-12:55 am

1 stop7h 25m

$329

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 9/22

8:15 am-5:55 am

2 stops21h 40m

Chicago O'Hare Intl

Tue 9/29

9:25 pm-4:27 pm

2 stops19h 02m

$648

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 9/23

5:00 am-8:40 pm

2 stops15h 40m

Chicago O'Hare Intl

Sat 9/26

6:55 am-9:27 pm

2 stops14h 32m

$655

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 $608.
The lowest price recently found on this route was $288.

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 $601. 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 $786.

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 at noon. Flights from Winnipeg to Chicago during this time can be as low as $642. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $658.

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.

How have Winnipeg to Chicago flight prices changed over time?

As of August 2026, prices for Winnipeg to Chicago flights are approximately 274% 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	$164
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 $164. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $288.

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).

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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 August 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 86.71% of the total bookings. Other popular models include Boeing 737-700 Passenger/BBJ1 (winglets) with 5.59%, Boeing 737 MAX 8 with 2.80%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 1.40%.
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 $335	Free Cancellation	Rating 7.4 10,136 reviews		Search United Airlines flights

United Airlines Flights From Winnipeg to Chicago
United Airlines flight deals from Winnipeg to Chicago start from $335 round-trip. Over the 8 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.

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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 $164

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 10/23. 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

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines 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?

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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According to popular flight searches on momondo this year