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

As of November 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 November 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.

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

WestJet is the most popular carrier operating from Chicago to Winnipeg

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$ 114 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$ 602 to C$ 989. The lowest price recently found on this route was C$ 296.

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Find the cheapest flights from Chicago to Winnipeg

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

4:49 p.m. - 3:07 p.m.ORD-YWG

22h 18m1 stop

9:00 p.m. - 12:08 p.m.YWG-ORD

15h 08m2 stops

C$ 296Multiple Airlines

Find Deal

Thu, 8 Jan - Thu, 15 Jan

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$ 305WestJet

Find Deal

Fri, 23 Jan - Mon, 26 Jan

6:10 a.m. - 3:07 p.m.MDW-YWG

8h 57m1 stop

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

15h 05m2 stops

C$ 308Multiple Airlines

Find Deal

Fri, 16 Jan - Mon, 19 Jan

5:50 a.m. - 3:07 p.m.ORD-YWG

9h 17m1 stop

4:10 p.m. - 4:52 p.m.YWG-ORD

24h 42m2 stops

C$ 308Multiple Airlines

Find Deal

Fri, 9 Jan - Fri, 16 Jan

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$ 310WestJet

Find Deal

Fri, 9 Jan - Fri, 16 Jan

5:50 a.m. - 3:07 p.m.ORD-YWG

9h 17m1 stop

7:30 a.m. - 10:44 p.m.YWG-ORD

15h 14m1 stop

C$ 315Multiple Airlines

Find Deal

Fri, 9 Jan - Fri, 16 Jan

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

8h 47m1 stop

12:55 p.m. - 10:43 a.m.YWG-ORD

21h 48m2 stops

C$ 317Multiple Airlines

Find Deal

Fri, 16 Jan - Sun, 18 Jan

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

8h 47m1 stop

4:55 p.m. - 10:43 a.m.YWG-ORD

17h 48m1 stop

C$ 325Multiple Airlines

Find Deal

Fri, 16 Jan - Sun, 18 Jan

6:00 a.m. - 3:09 p.m.MDW-YWG

9h 09m1 stop

6:15 a.m. - 11:25 p.m.YWG-MDW

17h 10m2 stops

C$ 333Multiple Airlines

Find Deal

Sun, 1 Mar - Thu, 5 Mar

11:00 a.m. - 11:35 p.m.MDW-YWG

12h 35m1 stop

4:25 p.m. - 10:10 a.m.YWG-MDW

17h 45m2 stops

C$ 439Porter Airlines

Find Deal

Fri, 16 Jan - Sun, 18 Jan

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

23 Jan

ORD2:20 p.m.Chicago O'Hare Intl

8h 21m

1 stop

YWG10:41 p.m.Winnipeg

26 Jan

YWG6:15 a.m.Winnipeg

7h 20m

1 stop

ORD1:35 p.m.Chicago O'Hare Intl

C$ 305

Find similar

WestJet

9 Jan

ORD2:20 p.m.Chicago O'Hare Intl

8h 21m

1 stop

YWG10:41 p.m.Winnipeg

16 Jan

YWG6:15 a.m.Winnipeg

7h 20m

1 stop

ORD1:35 p.m.Chicago O'Hare Intl

C$ 310

Find similar

WestJet

30 Apr

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

16h 30m

1 stop

YWG10:00 a.m.Winnipeg

3 May

YWG8:30 a.m.Winnipeg

8h 13m

1 stop

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

C$ 378

Find similar

Air Canada flights from Chicago to Winnipeg

Our best Air Canada deals on Chicago to Winnipeg flight tickets

Air Canada

23 Apr

ORD2:00 p.m.Chicago O'Hare Intl

7h 37m

1 stop

YWG9:37 p.m.Winnipeg

28 Apr

YWG8:00 a.m.Winnipeg

9h 07m

1 stop

ORD5:07 p.m.Chicago O'Hare Intl

C$ 646

Find similar

Air Canada

16 Jan

ORD2:00 p.m.Chicago O'Hare Intl

7h 44m

1 stop

YWG9:44 p.m.Winnipeg

19 Jan

YWG5:30 a.m.Winnipeg

7h 31m

1 stop

ORD1:01 p.m.Chicago O'Hare Intl

C$ 656

Find similar

Air Canada

10 Jan

ORD10:00 a.m.Chicago O'Hare Intl

7h 19m

1 stop

YWG5:19 p.m.Winnipeg

17 Jan

YWG11:05 a.m.Winnipeg

6h 43m

1 stop

ORD5:48 p.m.Chicago O'Hare Intl

C$ 659

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 8/1

4:49 p.m.-3:07 p.m.

1 stop22h 18m

Winnipeg

Thu 15/1

9:00 p.m.-12:08 p.m.

2 stops15h 08m

C$ 296

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 23/1

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

1 stop8h 21m

Winnipeg

Mon 26/1

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

1 stop7h 20m

C$ 305

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 16/1

6:10 a.m.-3:07 p.m.

1 stop8h 57m

Winnipeg

Mon 19/1

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

2 stops15h 05m

C$ 308

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/1

5:50 a.m.-3:07 p.m.

1 stop9h 17m

Winnipeg

Fri 16/1

4:10 p.m.-4:52 p.m.

2 stops24h 42m

C$ 308

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/1

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

1 stop8h 21m

Winnipeg

Fri 16/1

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

1 stop7h 20m

C$ 310

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/1

5:50 a.m.-3:07 p.m.

1 stop9h 17m

Winnipeg

Fri 16/1

7:30 a.m.-10:44 p.m.

1 stop15h 14m

C$ 315

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 16/1

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

1 stop8h 47m

Winnipeg

Sun 18/1

12:55 p.m.-10:43 a.m.

2 stops21h 48m

C$ 317

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 16/1

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

1 stop8h 47m

Winnipeg

Sun 18/1

4:55 p.m.-10:43 a.m.

1 stop17h 48m

C$ 325

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 1/3

6:00 a.m.-3:09 p.m.

1 stop9h 09m

Winnipeg

Thu 5/3

6:15 a.m.-11:25 p.m.

2 stops17h 10m

C$ 333

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 16/1

11:00 a.m.-11:35 p.m.

1 stop12h 35m

Winnipeg

Sun 18/1

4:25 p.m.-10:10 a.m.

2 stops17h 45m

C$ 439

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 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$ 382, 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$ 450.

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$ 452. 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$ 1,024.

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$ 452. 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$ 948. 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 49% 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 24m
Direct flights	Every day
Airports in Winnipeg	1 airport

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

Direct flights go from Chicago to Winnipeg every day.

There is 1 airport near Winnipeg: 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 4h 22m 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 70.83% of the total bookings. Other popular models include Boeing 777-300ER with 6.94%, Boeing 737 MAX 8 with 4.17%, and Airbus A319 with 2.78%.

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.