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

As of December 2025, 21 flights take off from Chicago and land in Winnipeg each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.

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

As of December 2025, there are 3 flights per day flying from Chicago to Winnipeg. The most common time of day flights depart is 9:00a.m., with 100% of flights taking off at noon.

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

Prices for flights from Chicago to Winnipeg Airport are updated daily.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Winnipeg Airport.

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

The necessary travel and health documents for your Winnipeg Airport 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.

C$ 110 Cheap Flights from Chicago to Winnipeg in 2025/26

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

Prices are currently low for flights on this route. Typical prices usually range from C$ 596 to C$ 978. The lowest price recently found on this route was C$ 308.

1 adult

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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.

5:01 p.m. - 3:07 p.m.

MDW

YWG

22h 06m1 stop

7:30 a.m. - 10:19 p.m.

YWG

MDW

14h 49m1 stop

C$ 308Multiple Airlines

Thu, 29 Jan - Sun, 1 Feb

6:20 a.m. - 3:07 p.m.

MDW

YWG

8h 47m1 stop

9:00 p.m. - 12:05 p.m.

YWG

MDW

15h 05m2 stops

C$ 317Multiple Airlines

Fri, 30 Jan - Mon, 2 Feb

4:41 p.m. - 3:07 p.m.

ORD

YWG

22h 26m1 stop

9:00 p.m. - 1:37 p.m.

YWG

ORD

16h 37m2 stops

C$ 328Multiple Airlines

Sat, 17 Jan - Sat, 24 Jan

5:40 a.m. - 3:07 p.m.

ORD

YWG

9h 27m1 stop

9:00 p.m. - 1:58 p.m.

YWG

ORD

16h 58m2 stops

C$ 342Multiple Airlines

Fri, 30 Jan - Mon, 2 Feb

2:20 p.m. - 10:41 p.m.

ORD

YWG

8h 21m1 stop

6:15 a.m. - 1:35 p.m.

YWG

ORD

7h 20m1 stop

C$ 345WestJet

Fri, 30 Jan - Mon, 2 Feb

5:40 a.m. - 3:07 p.m.

ORD

YWG

9h 27m1 stop

8:00 a.m. - 7:38 p.m.

YWG

ORD

11h 38m1 stop

C$ 348Multiple Airlines

Fri, 30 Jan - Mon, 2 Feb

2:42 p.m. - 3:07 p.m.

ORD

YWG

24h 25m1 stop

7:30 a.m. - 10:46 p.m.

YWG

ORD

15h 16m1 stop

C$ 412Multiple Airlines

Thu, 22 Jan - Sun, 25 Jan

5:30 p.m. - 10:00 a.m.

ORD

YWG

16h 30m1 stop

8:30 a.m. - 4:43 p.m.

YWG

ORD

8h 13m1 stop

C$ 429WestJet

Mon, 25 May - Mon, 1 Jun

11:05 a.m. - 11:13 a.m.

MDW

YWG

24h 08m2 stops

6:00 a.m. - 3:20 p.m.

YWG

MDW

9h 20m1 stop

C$ 616Porter Airlines

Thu, 29 Jan - Sun, 1 Feb

9:20 a.m. - 4:54 p.m.

MDW

YWG

7h 34m1 stop

6:40 a.m. - 1:07 p.m.

YWG

MDW

6h 27m1 stop

C$ 896Delta

Mon, 25 May - Mon, 1 Jun

Air Canada flights from Chicago to Winnipeg

Our best Air Canada deals on Chicago to Winnipeg flight tickets

Air Canada

15 Jan

ORD9:10 a.m.Chicago O'Hare Intl

2h 47m

YWG11:57 a.m.Winnipeg

22 Jan

YWG8:00 a.m.Winnipeg

9h 08m

1 stop

ORD5:08 p.m.Chicago O'Hare Intl

C$ 680

Find similar

Air Canada

15 Jan

ORD9:10 a.m.Chicago O'Hare Intl

2h 47m

YWG11:57 a.m.Winnipeg

22 Jan

YWG2:20 p.m.Winnipeg

2h 43m

ORD5:03 p.m.Chicago O'Hare Intl

C$ 758

Find similar

Air Canada

8 Dec

ORD8:45 a.m.Chicago O'Hare Intl

6h 58m

1 stop

YWG3:43 p.m.Winnipeg

9 Dec

YWG8:00 a.m.Winnipeg

9h 10m

1 stop

ORD5:10 p.m.Chicago O'Hare Intl

C$ 1,080

Find similar

Delta flights from Chicago to Winnipeg

Our best Delta deals on Chicago to Winnipeg flight tickets

Delta

8 Jan

MDW9:50 a.m.Chicago Midway

25h 13m

1 stop

YWG11:03 a.m.Winnipeg

11 Jan

YWG5:21 p.m.Winnipeg

25h 11m

1 stop

MDW6:32 p.m.Chicago Midway

C$ 729

Find similar

Delta

8 Jan

MDW6:45 a.m.Chicago Midway

16h 53m

2 stops

YWG11:38 p.m.Winnipeg

11 Jan

YWG5:21 p.m.Winnipeg

25h 11m

1 stop

MDW6:32 p.m.Chicago Midway

C$ 798

Find similar

Delta

8 Jan

MDW6:45 a.m.Chicago Midway

16h 53m

2 stops

YWG11:38 p.m.Winnipeg

11 Jan

YWG5:21 p.m.Winnipeg

19h 27m

2 stops

MDW12:48 p.m.Chicago Midway

C$ 800

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 29/1

5:01 p.m.-3:07 p.m.

1 stop22h 06m

Winnipeg

Sun 1/2

7:30 a.m.-10:19 p.m.

1 stop14h 49m

C$ 308

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 30/1

6:20 a.m.-3:07 p.m.

1 stop8h 47m

Winnipeg

Mon 2/2

9:00 p.m.-12:05 p.m.

2 stops15h 05m

C$ 317

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 17/1

4:41 p.m.-3:07 p.m.

1 stop22h 26m

Winnipeg

Sat 24/1

9:00 p.m.-1:37 p.m.

2 stops16h 37m

C$ 328

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 30/1

5:40 a.m.-3:07 p.m.

1 stop9h 27m

Winnipeg

Mon 2/2

9:00 p.m.-1:58 p.m.

2 stops16h 58m

C$ 342

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 30/1

2:20 p.m.-10:41 p.m.

1 stop8h 21m

Winnipeg

Mon 2/2

6:15 a.m.-1:35 p.m.

1 stop7h 20m

C$ 345

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 30/1

5:40 a.m.-3:07 p.m.

1 stop9h 27m

Winnipeg

Mon 2/2

8:00 a.m.-7:38 p.m.

1 stop11h 38m

C$ 348

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 22/1

2:42 p.m.-3:07 p.m.

1 stop24h 25m

Winnipeg

Sun 25/1

7:30 a.m.-10:46 p.m.

1 stop15h 16m

C$ 412

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 25/5

5:30 p.m.-10:00 a.m.

1 stop16h 30m

Winnipeg

Mon 1/6

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 429

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 29/1

11:05 a.m.-11:13 a.m.

2 stops24h 08m

Winnipeg

Sun 1/2

6:00 a.m.-3:20 p.m.

1 stop9h 20m

C$ 616

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 25/5

9:20 a.m.-4:54 p.m.

1 stop7h 34m

Winnipeg

Mon 1/6

6:40 a.m.-1:07 p.m.

1 stop6h 27m

C$ 896

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

Other information

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

What is the cheapest month to fly to Winnipeg?

The cheapest month to fly to Winnipeg from Chicago is in May. Flight prices, which tend to average around C$ 378, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of May, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around C$ 445.

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

Our data shows that Tuesday is the least expensive day to fly to Winnipeg. Tickets to fly out on this day can be as low as C$ 447. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Saturday is C$ 1,013.

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

In the morning is the cheapest time of day to fly from Chicago to Winnipeg when you can find flight prices for as low as C$ 448. Flying to Winnipeg in the morning is an ideal time because this is during off-peak travel hours. Flights to Winnipeg are more costly in the evening, with an average ticket price of C$ 938. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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?

No. A direct flight is the cheapest option for a flight between Chicago to Winnipeg.

How have Chicago to Winnipeg flight prices changed over time?

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

Fastest flight time	2h 24m
Direct flights	Tue, Wed, Thu, Fri, Sat and Sun
Airports in Winnipeg	1 airport

The fastest flight from Chicago to Winnipeg takes 2h 24m

Direct flights go from Chicago to Winnipeg on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.

There is 1 airport near Winnipeg: Winnipeg (YWG)

Search flight deals

How far is Chicago to Winnipeg by plane?
A flight from Chicago to Winnipeg will travel around 1153.0 km. Typically, this will take 2h 47m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to Winnipeg Airport?
Prices for flights from Chicago to Winnipeg Airport are updated daily.
How old do you have to be to fly from Chicago to Winnipeg Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The necessary travel and health documents for your Winnipeg Airport 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 Chicago to Winnipeg?
Based on momondo bookings for flights between Chicago and Winnipeg, the leading plane model is Embraer 175 (Enhanced Winglets), making up 70.00% of the total bookings. Other popular models include Boeing 777-300ER with 7.14%, Boeing 737 MAX 8 with 4.29%, and Airbus A319 with 2.86%.

Morden

Selkirk

Portage la Prairie

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Winnipeg for you.

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?

momondo helps you find the best flight between Chicago and Winnipeg by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Winnipeg, momondo offers a useful price alert feature which will track prices for flights to Winnipeg from Chicago and alert you when they change.