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

As of January 2026, 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

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

As of January 2026, 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.

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$ 182 Cheap Flights from Chicago to Winnipeg in 2026

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.

9:15 a.m. - 12:41 a.m.

ORD

YWG

15h 26m

2 stops

7:30 a.m. - 4:52 p.m.

YWG

ORD

9h 22m

1 stop

C$ 315Multiple Airlines

Tue, 3 Mar - Wed, 4 Mar

2:20 p.m. - 10:40 p.m.

ORD

YWG

8h 20m

1 stop

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

YWG

ORD

7h 20m

1 stop

C$ 351WestJet

Mon, 13 Apr - Fri, 17 Apr

2:20 p.m. - 12:40 a.m.

ORD

YWG

10h 20m

1 stop

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

YWG

ORD

7h 20m

1 stop

C$ 357WestJet

Fri, 27 Feb - Fri, 6 Mar

5:30 p.m. - 11:00 p.m.

ORD

YWG

29h 30m

1 stop

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

YWG

ORD

8h 13m

1 stop

C$ 360WestJet

Fri, 15 May - Sun, 17 May

1:40 p.m. - 11:10 p.m.

ORD

YWG

9h 30m

1 stop

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

YWG

ORD

8h 13m

1 stop

C$ 362WestJet

Sat, 11 Jul - Fri, 17 Jul

5:30 p.m. - 11:40 a.m.

ORD

YWG

18h 10m

1 stop

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

YWG

ORD

8h 13m

1 stop

C$ 364WestJet

Fri, 15 May - Sun, 17 May

2:20 p.m. - 10:07 a.m.

ORD

YWG

19h 47m

1 stop

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

YWG

ORD

7h 20m

1 stop

C$ 375WestJet

Mon, 16 Feb - Fri, 20 Feb

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

ORD

YWG

21h 00m

1 stop

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

YWG

ORD

8h 13m

1 stop

C$ 383WestJet

Fri, 5 Jun - Sun, 7 Jun

2:42 p.m. - 3:09 p.m.

ORD

YWG

24h 27m

1 stop

7:30 a.m. - 10:14 p.m.

YWG

ORD

14h 44m

1 stop

C$ 389Multiple Airlines

Thu, 5 Feb - Sun, 8 Feb

5:30 p.m. - 11:00 p.m.

ORD

YWG

29h 30m

1 stop

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

YWG

ORD

8h 13m

1 stop

C$ 397WestJet

Fri, 5 Jun - Sun, 7 Jun

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

13 Apr

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

8h 20m

1 stop

YWG10:40 p.m.Winnipeg

17 Apr

YWG6:15 a.m.Winnipeg

7h 20m

1 stop

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

C$ 351

WestJet

27 Feb

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

10h 20m

1 stop

YWG12:40 a.m.Winnipeg

6 Mar

YWG6:15 a.m.Winnipeg

7h 20m

1 stop

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

C$ 357

WestJet

15 May

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

29h 30m

1 stop

YWG11:00 p.m.Winnipeg

17 May

YWG8:30 a.m.Winnipeg

8h 13m

1 stop

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

C$ 360

Air Canada flights from Chicago to Winnipeg

Our best Air Canada deals on Chicago to Winnipeg flight tickets

Air Canada

22 Jan

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

7h 44m

1 stop

YWG9:44 p.m.Winnipeg

19 Feb

YWG2:20 p.m.Winnipeg

2h 25m

ORD4:45 p.m.Chicago O'Hare Intl

C$ 1,029

Air Canada

22 Jan

ORD3:35 p.m.Chicago O'Hare Intl

9h 39m

1 stop

YWG1:14 a.m.Winnipeg

19 Feb

YWG6:00 a.m.Winnipeg

8h 55m

2 stops

ORD2:55 p.m.Chicago O'Hare Intl

C$ 1,041

Air Canada

22 Jan

ORD3:55 p.m.Chicago O'Hare Intl

7h 59m

1 stop

YWG11:54 p.m.Winnipeg

5 Feb

YWG2:20 p.m.Winnipeg

2h 43m

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

C$ 1,073

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 3/3

9:15 a.m.-12:41 a.m.

2 stops15h 26m

Winnipeg

Wed 4/3

7:30 a.m.-4:52 p.m.

1 stop9h 22m

C$ 315

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 13/4

2:20 p.m.-10:40 p.m.

1 stop8h 20m

Winnipeg

Fri 17/4

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

1 stop7h 20m

C$ 351

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 27/2

2:20 p.m.-12:40 a.m.

1 stop10h 20m

Winnipeg

Fri 6/3

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

1 stop7h 20m

C$ 357

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 15/5

5:30 p.m.-11:00 p.m.

1 stop29h 30m

Winnipeg

Sun 17/5

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

1 stop8h 13m

C$ 360

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 11/7

1:40 p.m.-11:10 p.m.

1 stop9h 30m

Winnipeg

Fri 17/7

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

1 stop8h 13m

C$ 362

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 15/5

5:30 p.m.-11:40 a.m.

1 stop18h 10m

Winnipeg

Sun 17/5

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

1 stop8h 13m

C$ 364

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 16/2

2:20 p.m.-10:07 a.m.

1 stop19h 47m

Winnipeg

Fri 20/2

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

1 stop7h 20m

C$ 375

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

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

1 stop21h 00m

Winnipeg

Sun 7/6

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

1 stop8h 13m

C$ 383

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 5/2

2:42 p.m.-3:09 p.m.

1 stop24h 27m

Winnipeg

Sun 8/2

7:30 a.m.-10:14 p.m.

1 stop14h 44m

C$ 389

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-11:00 p.m.

1 stop29h 30m

Winnipeg

Sun 7/6

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

1 stop8h 13m

C$ 397

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?

The cheapest month to fly to Winnipeg from Chicago is in May. Flight prices, which tend to average around C$ 376, 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 August is also very affordable. Most momondo users find prices during this month for around C$ 622.

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$ 445. Be sure to avoid booking your departure on a Wednesday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Wednesday is C$ 887.

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$ 445. 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$ 933. 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	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 in Winnipeg. From Chicago there are direct flights to 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 24m 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 737 MAX 8 with 4.41%, Boeing 777-300ER with 4.41%, and Airbus A319 with 2.94%.

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.