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$ 115 Cheap Flights from Chicago to Winnipeg in 2025/26

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.

5:30 p.m. - 2:30 p.m.

ORD

YWG

21h 00m1 stop

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

YWG

ORD

8h 13m1 stop

C$ 333WestJet

Thu, 21 May - Tue, 26 May

5:30 p.m. - 5:40 p.m.

ORD

YWG

24h 10m1 stop

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

YWG

ORD

8h 13m1 stop

C$ 351WestJet

Fri, 5 Jun - Sun, 7 Jun

5:30 p.m. - 9:30 p.m.

ORD

YWG

28h 00m1 stop

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

YWG

ORD

8h 13m1 stop

C$ 355WestJet

Mon, 1 Jun - Mon, 8 Jun

5:32 p.m. - 3:30 p.m.

ORD

YWG

21h 58m2 stops

8:00 a.m. - 11:22 a.m.

YWG

ORD

27h 22m1 stop

C$ 370Multiple Airlines

Wed, 4 Feb - Mon, 9 Feb

5:15 a.m. - 7:12 p.m.

ORD

YWG

13h 57m2 stops

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

YWG

ORD

15h 16m1 stop

C$ 373Multiple Airlines

Thu, 29 Jan - Sun, 1 Feb

7:20 a.m. - 11:32 a.m.

ORD

YWG

28h 12m2 stops

8:00 a.m. - 9:03 p.m.

YWG

ORD

13h 03m1 stop

C$ 376Multiple Airlines

Wed, 4 Feb - Mon, 9 Feb

5:30 p.m. - 8:48 p.m.

ORD

YWG

27h 18m2 stops

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

YWG

ORD

8h 13m1 stop

C$ 379WestJet

Fri, 5 Jun - Sun, 7 Jun

7:00 p.m. - 5:26 p.m.

MDW

YWG

22h 26m1 stop

9:00 p.m. - 7:07 p.m.

YWG

MDW

22h 07m2 stops

C$ 379Multiple Airlines

Mon, 9 Feb - Mon, 16 Feb

5:30 p.m. - 8:48 p.m.

ORD

YWG

27h 18m2 stops

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

YWG

ORD

8h 13m1 stop

C$ 380WestJet

Fri, 5 Jun - Sun, 7 Jun

5:30 p.m. - 5:25 p.m.

ORD

YWG

23h 55m2 stops

7:00 a.m. - 4:43 p.m.

YWG

ORD

9h 43m2 stops

C$ 390WestJet

Fri, 5 Jun - Sun, 7 Jun

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

21 May

ORD5:30 p.m.Chicago O'Hare Intl

21h 00m

1 stop

YWG2:30 p.m.Winnipeg

26 May

YWG8:30 a.m.Winnipeg

8h 13m

1 stop

ORD4:43 p.m.Chicago O'Hare Intl

C$ 333

Find similar

WestJet

5 Jun

ORD5:30 p.m.Chicago O'Hare Intl

28h 00m

1 stop

YWG9:30 p.m.Winnipeg

7 Jun

YWG8:30 a.m.Winnipeg

8h 13m

1 stop

ORD4:43 p.m.Chicago O'Hare Intl

C$ 351

Find similar

WestJet

1 Jun

ORD5:30 p.m.Chicago O'Hare Intl

28h 00m

1 stop

YWG9:30 p.m.Winnipeg

8 Jun

YWG8:30 a.m.Winnipeg

8h 13m

1 stop

ORD4:43 p.m.Chicago O'Hare Intl

C$ 355

Find similar

Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

Porter Airlines

23 Apr

ORD8:00 a.m.Chicago O'Hare Intl

15h 35m

1 stop

YWG11:35 p.m.Winnipeg

28 Apr

YWG12:10 p.m.Winnipeg

7h 25m

1 stop

ORD7:35 p.m.Chicago O'Hare Intl

C$ 750

Find similar

Porter Airlines

23 Apr

ORD8:00 a.m.Chicago O'Hare Intl

7h 30m

1 stop

YWG3:30 p.m.Winnipeg

28 Apr

YWG12:10 p.m.Winnipeg

7h 25m

1 stop

ORD7:35 p.m.Chicago O'Hare Intl

C$ 764

Find similar

Porter Airlines

4 Feb

MDW11:00 a.m.Chicago Midway

24h 13m

2 stops

YWG11:13 a.m.Winnipeg

9 Feb

YWG4:25 p.m.Winnipeg

17h 40m

2 stops

MDW10:05 a.m.Chicago Midway

C$ 912

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 21/5

5:30 p.m.-2:30 p.m.

1 stop21h 00m

Winnipeg

Tue 26/5

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

1 stop8h 13m

C$ 333

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-5:40 p.m.

1 stop24h 10m

Winnipeg

Sun 7/6

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

1 stop8h 13m

C$ 351

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 1/6

5:30 p.m.-9:30 p.m.

1 stop28h 00m

Winnipeg

Mon 8/6

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

1 stop8h 13m

C$ 355

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 4/2

5:32 p.m.-3:30 p.m.

2 stops21h 58m

Winnipeg

Mon 9/2

8:00 a.m.-11:22 a.m.

1 stop27h 22m

C$ 370

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 29/1

5:15 a.m.-7:12 p.m.

2 stops13h 57m

Winnipeg

Sun 1/2

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

1 stop15h 16m

C$ 373

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 4/2

7:20 a.m.-11:32 a.m.

2 stops28h 12m

Winnipeg

Mon 9/2

8:00 a.m.-9:03 p.m.

1 stop13h 03m

C$ 376

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-8:48 p.m.

2 stops27h 18m

Winnipeg

Sun 7/6

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

1 stop8h 13m

C$ 379

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 9/2

7:00 p.m.-5:26 p.m.

1 stop22h 26m

Winnipeg

Mon 16/2

9:00 p.m.-7:07 p.m.

2 stops22h 07m

C$ 379

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-8:48 p.m.

2 stops27h 18m

Winnipeg

Sun 7/6

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

1 stop8h 13m

C$ 380

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-5:25 p.m.

2 stops23h 55m

Winnipeg

Sun 7/6

7:00 a.m.-4:43 p.m.

2 stops9h 43m

C$ 390

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 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$ 370, 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$ 436.

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$ 438. 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$ 992.

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$ 438. 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$ 919. 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?

You could potentially save up to 47% on your flight if you consider stops on a Chicago to Winnipeg flight.

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 34m
Direct flights	Every day
Airports in Winnipeg	1 airport

The fastest flight from Chicago to Winnipeg takes 2h 34m

Direct flights go from Chicago to Winnipeg every day.

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

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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 34m 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 75.00% of the total bookings. Other popular models include Boeing 777-300ER with 6.25%, Boeing 737 MAX 8 with 3.75%, and Airbus A319 with 2.50%.

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.