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 day?

As of February 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.

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

As of February 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$ 227 Cheap Flights from Chicago to Winnipeg in 2026

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$ 1,004 to C$ 1,068. The lowest price recently found on this route was C$ 291.

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Find the cheapest flights from Chicago to Winnipeg

Round-trip

One-way

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:30 p.m. - 12:55 a.m.

ORD

YWG

7h 25m

1 stop

7:00 a.m. - 4:40 p.m.

YWG

ORD

9h 40m

1 stop

C$ 309WestJet

Fri, 15 May - Mon, 18 May

5:30 p.m. - 12:55 a.m.

ORD

YWG

7h 25m

1 stop

7:00 a.m. - 4:40 p.m.

YWG

ORD

9h 40m

1 stop

C$ 321WestJet

Mon, 25 May - Fri, 29 May

5:30 p.m. - 12:55 a.m.

ORD

YWG

7h 25m

1 stop

7:00 a.m. - 4:40 p.m.

YWG

ORD

9h 40m

1 stop

C$ 337WestJet

Fri, 8 May - Sun, 10 May

5:30 p.m. - 12:55 a.m.

ORD

YWG

7h 25m

1 stop

10:15 p.m. - 4:40 p.m.

YWG

ORD

18h 25m

2 stops

C$ 361WestJet

Fri, 15 May - Mon, 18 May

5:30 p.m. - 12:55 a.m.

ORD

YWG

7h 25m

1 stop

9:05 p.m. - 2:15 p.m.

YWG

ORD

17h 10m

2 stops

C$ 386Multiple Airlines

Mon, 25 May - Fri, 29 May

5:30 p.m. - 9:20 a.m.

ORD

YWG

15h 50m

2 stops

7:00 a.m. - 4:40 p.m.

YWG

ORD

9h 40m

2 stops

C$ 389WestJet

Fri, 15 May - Mon, 18 May

5:30 p.m. - 12:55 a.m.

ORD

YWG

7h 25m

1 stop

9:05 p.m. - 10:44 a.m.

YWG

ORD

13h 39m

2 stops

C$ 402Multiple Airlines

Fri, 8 May - Sun, 10 May

4:28 p.m. - 3:09 p.m.

ORD

YWG

22h 41m

1 stop

9:05 p.m. - 10:44 a.m.

YWG

ORD

13h 39m

2 stops

C$ 403Multiple Airlines

Tue, 21 Apr - Tue, 5 May

8:43 a.m. - 10:10 p.m.

ORD

YWG

13h 27m

2 stops

7:00 a.m. - 4:40 p.m.

YWG

ORD

9h 40m

1 stop

C$ 432Multiple Airlines

Sat, 16 May - Fri, 22 May

5:30 p.m. - 12:55 a.m.

ORD

YWG

7h 25m

1 stop

7:00 a.m. - 4:40 p.m.

YWG

ORD

9h 40m

1 stop

C$ 441WestJet

Fri, 5 Jun - Sun, 7 Jun

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

15 May

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

18 May

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

C$ 309

WestJet

25 May

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

29 May

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

C$ 321

WestJet

8 May

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

10 May

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

C$ 337

Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

Porter Airlines

25 May

MDW5:35 p.m.Chicago Midway

24h 23m

2 stops

YWG5:58 p.m.Winnipeg

29 May

YWG4:15 p.m.Winnipeg

17h 25m

2 stops

MDW9:40 a.m.Chicago Midway

C$ 950

Porter Airlines

8 May

MDW10:25 a.m.Chicago Midway

31h 33m

2 stops

YWG5:58 p.m.Winnipeg

10 May

YWG4:15 p.m.Winnipeg

24h 35m

2 stops

MDW4:50 p.m.Chicago Midway

C$ 986

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 15/5

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Mon 18/5

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 309

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 25/5

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Fri 29/5

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 321

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 8/5

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sun 10/5

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 337

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 15/5

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Mon 18/5

10:15 p.m.-4:40 p.m.

2 stops18h 25m

C$ 361

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 25/5

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Fri 29/5

9:05 p.m.-2:15 p.m.

2 stops17h 10m

C$ 386

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 15/5

5:30 p.m.-9:20 a.m.

2 stops15h 50m

Winnipeg

Mon 18/5

7:00 a.m.-4:40 p.m.

2 stops9h 40m

C$ 389

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 8/5

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sun 10/5

9:05 p.m.-10:44 a.m.

2 stops13h 39m

C$ 402

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 21/4

4:28 p.m.-3:09 p.m.

1 stop22h 41m

Winnipeg

Tue 5/5

9:05 p.m.-10:44 a.m.

2 stops13h 39m

C$ 403

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 16/5

8:43 a.m.-10:10 p.m.

2 stops13h 27m

Winnipeg

Fri 22/5

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 432

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sun 7/6

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 441

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$ 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 August is also very affordable. Most momondo users find prices during this month for around C$ 612.

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$ 437. 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$ 870.

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$ 918. 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	Mon, Tue, Wed, Thu, Fri and Sat
Airports in Winnipeg	1 airport

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

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

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 76.39% of the total bookings. Other popular models include Boeing 737 MAX 8 with 4.17%, Boeing 777-300ER 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.