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

WestJet is the most popular carrier operating from Manitoba to Chicago

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

28 flights are operational weekly from Manitoba to Chicago as of December 2025. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.

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

4 flights are operational daily from Manitoba to Chicago as of December 2025. The most popular departure time for this route is 2:00p.m., with 100% of flights per day taking off in the afternoon.

Which airlines fly to Chicago?

United Airlines, Air Canada and WestJet are the top three most popular airlines that fly to Chicago from Manitoba according to our data. United Airlines is the first choice among our users, with 48% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Manitoba to Chicago?

Prices for flights from Manitoba to Chicago refresh daily.

How many operators does momondo search for flights from Manitoba to Chicago?

There are 3 operators available for flights from Manitoba to Chicago as of December 2025.

How old do you have to be to fly from Manitoba to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Manitoba to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

C$ 168 Cheap Flights from Manitoba to Chicago in 2025/26

1 adult

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Find the cheapest flights from Manitoba to Chicago

Round-trip

One-way

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

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

YWG

ORD

7h 20m1 stop

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

ORD

YWG

8h 20m1 stop

C$ 269WestJet

Fri, 20 Feb - Mon, 23 Feb

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

YWG

ORD

8h 13m1 stop

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

ORD

YWG

28h 00m1 stop

C$ 275WestJet

Fri, 1 May - Mon, 4 May

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

YWG

ORD

7h 20m1 stop

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

ORD

YWG

8h 20m1 stop

C$ 277WestJet

Mon, 23 Feb - Mon, 9 Mar

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

YWG

ORD

8h 13m1 stop

5:30 p.m. - 10:00 a.m.

ORD

YWG

16h 30m1 stop

C$ 284WestJet

Fri, 1 May - Sun, 3 May

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

YWG

ORD

9h 22m1 stop

6:02 p.m. - 12:40 a.m.

ORD

YWG

30h 38m2 stops

C$ 293Multiple Airlines

Wed, 18 Feb - Wed, 4 Mar

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

YWG

ORD

8h 13m1 stop

5:30 p.m. - 10:00 a.m.

ORD

YWG

16h 30m1 stop

C$ 302WestJet

Wed, 27 May - Wed, 3 Jun

9:00 p.m. - 4:57 p.m.

YWG

ORD

19h 57m2 stops

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

ORD

YWG

8h 20m1 stop

C$ 304Multiple Airlines

Mon, 16 Feb - Fri, 27 Feb

4:10 p.m. - 2:54 p.m.

YWG

ORD

22h 44m2 stops

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

ORD

YWG

8h 20m1 stop

C$ 306Multiple Airlines

Wed, 18 Feb - Fri, 27 Feb

9:00 p.m. - 10:39 a.m.

YWG

ORD

13h 39m2 stops

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

ORD

YWG

8h 20m1 stop

C$ 310Multiple Airlines

Tue, 17 Feb - Fri, 27 Feb

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

YWG

ORD

7h 20m1 stop

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

ORD

YWG

8h 20m1 stop

C$ 312WestJet

Fri, 20 Feb - Mon, 9 Mar

WestJet flights from Manitoba to Chicago

Our best WestJet deals on Manitoba to Chicago flight tickets

WestJet

20 Feb

YWG6:15 a.m.Winnipeg

7h 20m

1 stop

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

23 Feb

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

8h 20m

1 stop

YWG10:40 p.m.Winnipeg

C$ 269

Find similar

WestJet

1 May

YWG8:30 a.m.Winnipeg

8h 13m

1 stop

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

4 May

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

28h 00m

1 stop

YWG9:30 p.m.Winnipeg

C$ 275

Find similar

WestJet

23 Feb

YWG6:15 a.m.Winnipeg

7h 20m

1 stop

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

9 Mar

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

8h 20m

1 stop

YWG10:40 p.m.Winnipeg

C$ 277

Find similar

United Airlines flights from Manitoba to Chicago

Our best United Airlines deals on Manitoba to Chicago flight tickets

United Airlines

27 Dec

YWG8:40 a.m.Winnipeg

15h 19m

1 stop

ORD11:59 p.m.Chicago O'Hare Intl

29 Jan

ORD9:10 a.m.Chicago O'Hare Intl

2h 47m

YWG11:57 a.m.Winnipeg

C$ 1,028

Find similar

United Airlines

27 Dec

YWG8:40 a.m.Winnipeg

10h 15m

1 stop

ORD6:55 p.m.Chicago O'Hare Intl

29 Jan

ORD1:13 p.m.Chicago O'Hare Intl

8h 31m

1 stop

YWG9:44 p.m.Winnipeg

C$ 1,038

Find similar

United Airlines

27 Dec

YWG8:40 a.m.Winnipeg

12h 39m

1 stop

ORD9:19 p.m.Chicago O'Hare Intl

29 Jan

ORD10:35 a.m.Chicago O'Hare Intl

13h 19m

2 stops

YWG11:54 p.m.Winnipeg

C$ 1,072

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 20/2

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

1 stop7h 20m

Chicago O'Hare Intl

Mon 23/2

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

1 stop8h 20m

C$ 269

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 1/5

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

1 stop8h 13m

Chicago O'Hare Intl

Mon 4/5

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

1 stop28h 00m

C$ 275

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 23/2

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

1 stop7h 20m

Chicago O'Hare Intl

Mon 9/3

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

1 stop8h 20m

C$ 277

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 1/5

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

1 stop8h 13m

Chicago O'Hare Intl

Sun 3/5

5:30 p.m.-10:00 a.m.

1 stop16h 30m

C$ 284

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 18/2

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

1 stop9h 22m

Chicago O'Hare Intl

Wed 4/3

6:02 p.m.-12:40 a.m.

2 stops30h 38m

C$ 293

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 27/5

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

1 stop8h 13m

Chicago O'Hare Intl

Wed 3/6

5:30 p.m.-10:00 a.m.

1 stop16h 30m

C$ 302

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 16/2

9:00 p.m.-4:57 p.m.

2 stops19h 57m

Chicago O'Hare Intl

Fri 27/2

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

1 stop8h 20m

C$ 304

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 18/2

4:10 p.m.-2:54 p.m.

2 stops22h 44m

Chicago O'Hare Intl

Fri 27/2

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

1 stop8h 20m

C$ 306

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 17/2

9:00 p.m.-10:39 a.m.

2 stops13h 39m

Chicago O'Hare Intl

Fri 27/2

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

1 stop8h 20m

C$ 310

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 20/2

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

1 stop7h 20m

Chicago O'Hare Intl

Mon 9/3

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

1 stop8h 20m

C$ 312

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 Manitoba to Chicago

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 Chicago?

The month of October is another great option to travel to Chicago, with average flight prices from Manitoba averaging around C$ 494.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as C$ 806. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 1,006. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the afternoon is the cheapest time of day to fly from Manitoba to Chicago when you can find flight prices for as low as C$ 707. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 895 per ticket.

What is the cheapest Manitoba to Chicago flight route?

Fly from Winnipeg to Chicago O'Hare Intl for the best Manitoba - Chicago flight prices

What cabin class options are available on Manitoba to Chicago flights?

There are 4 cabin classes available to choose from on Manitoba to Chicago 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 Manitoba to Chicago flights?

You could potentially save up to 22% on your flight if you consider stops on a Manitoba to Chicago flight.

Cheap Manitoba to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Manitoba to Chicago

Best price found	C$ 416
Fastest flight time	2h 21m
Direct flights	Mon, Tue, Thu, Fri, Sat and Sun
Airports in Chicago	3 airports

The best one-way flight to Chicago from Manitoba in the past 72 hours is C$ 416. The best round-trip flight deal from Manitoba to Chicago found on momondo in the last 72 hours is C$ 619.

The fastest flight from Manitoba to Chicago takes 2h 21m

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

There are 3 airports in Chicago. From Manitoba there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

When did momondo last update prices for flights from Manitoba to Chicago?
Prices for flights from Manitoba to Chicago refresh daily.
How many operators does momondo search for flights from Manitoba to Chicago?
There are 3 operators available for flights from Manitoba to Chicago as of December 2025.
How old do you have to be to fly from Manitoba to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Manitoba to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Manitoba to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Manitoba to Chicago is Embraer 175 (Enhanced Winglets), representing 49.66% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 13.79%, Boeing 737-800 Passenger/BBJ2 (winglets) at 8.97%, and Airbus A330-900neo at 5.52%.

Best airlines flying from Manitoba to Chicago

Compare and see reviews for airlines that fly from Manitoba to Chicago with momondo

Airline	Rating	Free Cancellation	Price
WestJet	PriceFrom C$ 200	Free Cancellation	Rating 7.2 3,208 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 486	Free Cancellation	Rating 7.4 9,099 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 496	Free Cancellation	Rating 7.1 10,549 reviews	Search Air Canada flights

Munster

Hammond

Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Manitoba to Chicago?

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 Manitoba to Chicago for you.

Can I find flights from Manitoba to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Manitoba with this policy.

How can momondo help me find flights from Manitoba to Chicago?

momondo helps you find the best flight between Manitoba and Chicago 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 Manitoba to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Manitoba and alert you when they change.