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.

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

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$ 127 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.

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

ORD

YWG

8h 20m1 stop

4:10 p.m. - 3:59 p.m.

YWG

ORD

23h 49m2 stops

C$ 315Multiple Airlines

vie., 13 mar. - dom., 15 mar.

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

ORD

YWG

8h 20m1 stop

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

YWG

ORD

7h 20m1 stop

C$ 317WestJet

vie., 20 feb. - vie., 27 feb.

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

ORD

YWG

8h 20m1 stop

4:55 p.m. - 3:59 p.m.

YWG

ORD

23h 04m1 stop

C$ 319Multiple Airlines

vie., 13 mar. - dom., 15 mar.

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

ORD

YWG

18h 10m1 stop

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

YWG

ORD

8h 13m1 stop

C$ 332WestJet

lun., 11 may. - lun., 1 jun.

5:40 a.m. - 3:09 p.m.

ORD

YWG

9h 29m1 stop

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

YWG

ORD

14h 44m1 stop

C$ 340Multiple Airlines

vie., 6 feb. - dom., 8 feb.

8:43 p.m. - 3:30 p.m.

ORD

YWG

18h 47m2 stops

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

YWG

ORD

27h 22m1 stop

C$ 348Multiple Airlines

lun., 2 feb. - lun., 9 feb.

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

ORD

YWG

10h 20m1 stop

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

YWG

ORD

7h 20m1 stop

C$ 350WestJet

lun., 2 feb. - lun., 9 feb.

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

dom., 28 jun. - jue., 9 jul.

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

ORD

YWG

18h 10m1 stop

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

YWG

ORD

8h 13m1 stop

C$ 354WestJet

vie., 5 jun. - dom., 7 jun.

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

ORD

YWG

18h 10m1 stop

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

YWG

ORD

8h 13m1 stop

C$ 361WestJet

vie., 26 jun. - jue., 9 jul.

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

20 Feb

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

8h 20m

1 stop

YWG10:40 p.m.Winnipeg

27 Feb

YWG6:15 a.m.Winnipeg

7h 20m

1 stop

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

C$ 317

WestJet

30 May

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

18h 10m

1 stop

YWG11:40 a.m.Winnipeg

7 Jun

YWG8:30 a.m.Winnipeg

8h 13m

1 stop

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

C$ 330

WestJet

11 May

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

18h 10m

1 stop

YWG11:40 a.m.Winnipeg

1 Jun

YWG8:30 a.m.Winnipeg

8h 13m

1 stop

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

C$ 332

Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

Porter Airlines

11 May

MDW9:40 a.m.Chicago Midway

13h 06m

2 stops

YWG10:46 p.m.Winnipeg

1 Jun

YWG6:10 a.m.Winnipeg

10h 14m

1 stop

MDW4:24 p.m.Chicago Midway

C$ 576

Porter Airlines

11 May

MDW9:40 a.m.Chicago Midway

13h 06m

2 stops

YWG10:46 p.m.Winnipeg

1 Jun

YWG11:45 a.m.Winnipeg

21h 00m

2 stops

MDW8:45 a.m.Chicago Midway

C$ 737

Porter Airlines

11 Jan

ORD3:37 p.m.Chicago O'Hare Intl

7h 58m

1 stop

YWG11:35 p.m.Winnipeg

15 Jan

YWG12:10 p.m.Winnipeg

7h 54m

1 stop

ORD8:04 p.m.Chicago O'Hare Intl

C$ 1,410

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 13/3

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

1 stop8h 20m

Winnipeg

dom. 15/3

4:10 p.m.-3:59 p.m.

2 stops23h 49m

C$ 315

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 20/2

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

1 stop8h 20m

Winnipeg

vie. 27/2

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

1 stop7h 20m

C$ 317

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 13/3

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

1 stop8h 20m

Winnipeg

dom. 15/3

4:55 p.m.-3:59 p.m.

1 stop23h 04m

C$ 319

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 11/5

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

1 stop18h 10m

Winnipeg

lun. 1/6

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

1 stop8h 13m

C$ 332

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 6/2

5:40 a.m.-3:09 p.m.

1 stop9h 29m

Winnipeg

dom. 8/2

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

1 stop14h 44m

C$ 340

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 2/2

8:43 p.m.-3:30 p.m.

2 stops18h 47m

Winnipeg

lun. 9/2

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

1 stop27h 22m

C$ 348

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 2/2

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

1 stop10h 20m

Winnipeg

lun. 9/2

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

1 stop7h 20m

C$ 350

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

dom. 28/6

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

1 stop24h 10m

Winnipeg

jue. 9/7

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

1 stop8h 13m

C$ 351

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 5/6

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

1 stop18h 10m

Winnipeg

dom. 7/6

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

1 stop8h 13m

C$ 354

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 26/6

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

1 stop18h 10m

Winnipeg

jue. 9/7

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

1 stop8h 13m

C$ 361

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 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$ 443. 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$ 883.

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$ 443. 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$ 929. 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 75.38% of the total bookings. Other popular models include Boeing 737 MAX 8 with 4.62%, Boeing 777-300ER with 4.62%, and Airbus A319 with 3.08%.

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.