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

47 flights are operational weekly from Chicago to Winnipeg as of September 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

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

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

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

The number of flights available between Chicago and Winnipeg is 6 per day as of September 2026. The most frequent departure time is 7:00PM, with 55% of daily flights leaving in the evening.

When did momondo last update prices for flights from Chicago to Winnipeg Airport?

Prices for flights from Chicago to Winnipeg Airport refresh daily.

How many operators does momondo search for flights from Chicago to Winnipeg Airport?

As of September 2026, there are 2 operators available to choose from for flights from Chicago to Winnipeg Airport.

How old do you have to be to fly from Chicago to Winnipeg Airport?

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 Chicago to Winnipeg Airport.

What documentation or ID do you need to fly to Winnipeg Airport?

The travel and health documents required for your trip to Winnipeg Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Winnipeg Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$145 Cheap Flights from Chicago to Winnipeg in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Winnipeg

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

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

7h 25m1 stop Calgary

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

9h 40m1 stop Calgary

$329WestJet

Fri, Oct 2 - Sun, Oct 4

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

7h 25m1 stop Calgary

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

9h 40m1 stop Calgary

$330WestJet

Thu, Oct 15 - Mon, Oct 19

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

7h 25m1 stop Calgary

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

9h 40m1 stop Calgary

$333WestJet

Sun, Oct 4 - Sun, Oct 11

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

7h 25m1 stop Calgary

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

9h 40m1 stop Calgary

$339WestJet

Mon, Oct 5 - Mon, Oct 12

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

9h 35m1 stop Toronto Island

6:05 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

16h 55m1 stop Toronto Pearson Intl

$361Multiple Airlines

Fri, Oct 2 - Sun, Oct 4

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

7h 25m1 stop Calgary

9:20 am - 4:14 pmYWG Winnipeg-ORD Chicago O'Hare Intl

6h 54m1 stop Toronto Pearson Intl

$381Multiple Airlines

Thu, Oct 15 - Tue, Oct 20

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

9h 35m1 stop Toronto Island

9:05 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

17h 30m2 stops Calgary Toronto Pearson Intl

$383Multiple Airlines

Fri, Oct 2 - Sun, Oct 4

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

2h 48mnonstop

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

2h 35mnonstop

$919United Airlines

Wed, Nov 4 - Wed, Nov 11

9:29 am - 12:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 54mnonstop

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

2h 35mnonstop

$935United Airlines

Thu, Oct 29 - Tue, Nov 3

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

2h 48mnonstop

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

2h 35mnonstop

$937United Airlines

Wed, Nov 4 - Wed, Nov 11

Cheap last minute flights

Enter your travel dates to find the best prices.

7:28 pm - 3:25 pmORD Chicago O'Hare Intl-YWG Winnipeg

19h 57m2 stops Atlanta Hartsfield-Jackson Calgary

9:05 pm - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

19h 35m1 stop Calgary

$578Multiple Airlines

Mon, Sep 14 - Wed, Sep 23

7:11 am - 7:49 pmORD Chicago O'Hare Intl-YWG Winnipeg

12h 38m2 stops Fort Lauderdale Toronto Pearson Intl

9:05 pm - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

19h 35m1 stop Calgary

$607Multiple Airlines

Tue, Sep 15 - Wed, Sep 23

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

7h 25m1 stop Calgary

9:05 pm - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

19h 35m1 stop Calgary

$718WestJet

Tue, Sep 15 - Wed, Sep 23

6:25 am - 10:10 pmMDW Chicago Midway-YWG Winnipeg

15h 45m2 stops Atlanta Hartsfield-Jackson Calgary

12:41 pm - 6:19 pmYWG Winnipeg-MDW Chicago Midway

5h 38m1 stop Minneapolis St Paul

$768Multiple Airlines

Tue, Sep 15 - Tue, Sep 22

7:11 am - 7:49 pmORD Chicago O'Hare Intl-YWG Winnipeg

12h 38m2 stops Fort Lauderdale Toronto Pearson Intl

3:58 pm - 9:33 pmYWG Winnipeg-ORD Chicago O'Hare Intl

5h 35m1 stop Minneapolis St Paul

$781Multiple Airlines

Tue, Sep 15 - Tue, Sep 22

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

7h 25m1 stop Calgary

5:44 pm - 9:33 pmYWG Winnipeg-ORD Chicago O'Hare Intl

3h 49m1 stop Minneapolis St Paul

$881WestJet

Tue, Sep 15 - Tue, Sep 22

12:29 pm - 4:54 pmORD Chicago O'Hare Intl-YWG Winnipeg

4h 25m1 stop Minneapolis St Paul

5:44 pm - 9:33 pmYWG Winnipeg-ORD Chicago O'Hare Intl

3h 49m1 stop Minneapolis St Paul

$1,026WestJet

Mon, Sep 14 - Tue, Sep 22

9:15 am - 11:52 amORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mnonstop

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

2h 35mnonstop

$1,408United Airlines

Sun, Sep 13 - Sun, Sep 20

9:15 am - 11:52 amORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mnonstop

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

2h 35mnonstop

$1,408United Airlines

Sun, Sep 13 - Thu, Sep 17

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

2h 39mnonstop

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

2h 35mnonstop

$1,408United Airlines

Sun, Sep 13 - Mon, Sep 21

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

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

Oct 2

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

Oct 4

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$329

WestJet

Oct 15

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

Oct 19

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$330

WestJet

Oct 4

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

Oct 11

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$333

Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

Porter Airlines

Nov 11

ORD2:50 pmChicago O'Hare Intl

7h 07m

1 stop

YWG9:57 pmWinnipeg

Nov 16

YWG7:00 amWinnipeg

7h 37m

1 stop

ORD2:37 pmChicago O'Hare Intl

$525

Porter Airlines

Nov 11

ORD2:50 pmChicago O'Hare Intl

7h 07m

1 stop

YWG9:57 pmWinnipeg

Nov 16

YWG7:00 amWinnipeg

7h 37m

1 stop

ORD2:37 pmChicago O'Hare Intl

$537

Porter Airlines

Sep 16

ORD11:42 amChicago O'Hare Intl

8h 12m

1 stop

YWG7:54 pmWinnipeg

Sep 23

YWG9:20 amWinnipeg

6h 58m

1 stop

ORD4:18 pmChicago O'Hare Intl

$663

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 10/2

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 10/4

7:00 am-4:40 pm

1 stop9h 40m

$329

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 10/15

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Mon 10/19

7:00 am-4:40 pm

1 stop9h 40m

$330

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 10/4

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 10/11

7:00 am-4:40 pm

1 stop9h 40m

$333

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 10/5

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Mon 10/12

7:00 am-4:40 pm

1 stop9h 40m

$339

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 10/2

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sun 10/4

6:05 pm-11:00 am

1 stop16h 55m

$361

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 10/15

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Tue 10/20

9:20 am-4:14 pm

1 stop6h 54m

$381

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 10/2

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sun 10/4

9:05 pm-2:35 pm

2 stops17h 30m

$383

Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 11/4

9:35 am-12:23 pm

Nonstop2h 48m

Winnipeg

Wed 11/11

2:15 pm-4:50 pm

Nonstop2h 35m

$919

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 10/29

9:29 am-12:23 pm

Nonstop2h 54m

Winnipeg

Tue 11/3

2:15 pm-4:50 pm

Nonstop2h 35m

$935

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 11/4

9:35 am-12:23 pm

Nonstop2h 48m

Winnipeg

Wed 11/11

2:15 pm-4:50 pm

Nonstop2h 35m

$937

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 Chicago to Winnipeg

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 Winnipeg?

In general, October is the cheapest month to fly from Chicago to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $479. If you’re not able to fly to Winnipeg in October, then March is your next best option. Flight prices from Chicago to Winnipeg during March average around $528.

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

The cheapest day to depart on your flight to Winnipeg is on a Saturday when prices can be found for as low as $755. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,150.

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

The cheapest time of day to fly to Winnipeg is at noon when flights can be purchased for as low as $661. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $900 on average. Flights to Winnipeg from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to Winnipeg flight route?

Fly from Chicago O'Hare Intl to Winnipeg for the best Chicago - Winnipeg flight prices

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

There is only 1 cabin class available to choose from on Chicago to Winnipeg 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 Chicago to Winnipeg flights?

You could potentially save up to 68% on your flight if you consider stops on a Chicago to Winnipeg flight.

How have Chicago to Winnipeg flight prices changed over time?

As of September 2026, prices for Chicago to Winnipeg flights are approximately 109% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Winnipeg

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Winnipeg according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

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

Find info about flight duration, direct flights, and airports for your flight from Chicago to Winnipeg

Best Price Found	$145
Fastest flight time	2h 37m
Direct flights	Every day
Airports in Winnipeg	1 airport

The best one-way flight to Winnipeg from Chicago in the past 72 hours is $145. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is $329.

The fastest flight from Chicago to Winnipeg takes 2h 37m

Direct flights go from Chicago to Winnipeg every day.

There is 1 airport in Winnipeg. From Chicago there are direct flights to Winnipeg (YWG).

Search flight deals

Frequently asked questions about flying from Chicago to Winnipeg

How far is Chicago to Winnipeg by plane?
A flight from Chicago to Winnipeg will travel around 716.4 mi. Flights usually cover this in 2h 37m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to Winnipeg Airport?
Prices for flights from Chicago to Winnipeg Airport refresh daily.
How many operators does momondo search for flights from Chicago to Winnipeg Airport?
As of September 2026, there are 2 operators available to choose from for flights from Chicago to Winnipeg Airport.
How old do you have to be to fly from Chicago to Winnipeg Airport?
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 Chicago to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The travel and health documents required for your trip to Winnipeg Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Winnipeg Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Winnipeg?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Winnipeg is Embraer 175 (Enhanced Winglets) (74.07% of total bookings). The next most popular plane models are Boeing 787-10 Dreamliner (7.41%), Boeing 777-300ER (7.41%), and Boeing 777-300 (7.41%).
What is the most popular airline from Chicago to Winnipeg?
momondo data reveals that the most frequently booked airline on the route from Chicago to Winnipeg is United Airlines, representing 67% of all bookings. The subsequent popular airline is Air Canada at 33%.

Best airlines flying from Chicago to Winnipeg

Compare and see reviews for airlines that fly from Chicago to Winnipeg with momondo

Airline	Rating	Free Cancellation	Price
WestJet	PriceFrom $208	Free Cancellation	Rating 7.2 3,447 reviews		Search WestJet flights
United Airlines	PriceFrom $362	Free Cancellation	Rating 7.4 10,190 reviews		Search United Airlines flights

United Airlines Flights From Chicago to Winnipeg
United Airlines flies from Chicago to Winnipeg around 14 times per week, with 10,194 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago to Winnipeg in the last 72 hours was $362 (round-trip), much lower than the average airfare cost of $762 for United Airlines flights on this route.

Selkirk

Portage la Prairie

Morden

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Winnipeg?

Finding the right flight to Winnipeg from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Winnipeg quick and easy, saving you time and money.

Can I find flights from Chicago to Winnipeg with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Winnipeg from Chicago with this policy.

How can momondo help me find flights from Chicago to Winnipeg?

Once you have performed a search for Chicago to Winnipeg flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Winnipeg right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Winnipeg now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Winnipeg and let you know when they change.