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Cheap flights from Manitoba to Chicago from C$ 154

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Manitoba to Chicago departing on 19/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Manitoba to Chicago

Cheap round-trip flights

WestJet Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
WestJet Logo
2:20 p.m. - 12:41 a.m.ORD-YWG
10h 21m1 stop
C$ 266WestJet
Find Deal
Fri, 14 Nov - Mon, 17 Nov
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 9:01 a.m.ORD-YWG
15h 31m1 stop
C$ 274WestJet
Find Deal
Thu, 2 Oct - Mon, 6 Oct
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 9:01 a.m.ORD-YWG
15h 31m1 stop
C$ 276WestJet
Find Deal
Thu, 2 Oct - Sun, 5 Oct
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 11:26 a.m.ORD-YWG
17h 56m2 stops
C$ 280WestJet
Find Deal
Thu, 2 Oct - Mon, 6 Oct
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 11:26 a.m.ORD-YWG
17h 56m2 stops
C$ 287WestJet
Find Deal
Thu, 2 Oct - Sun, 5 Oct
Logo
8:15 p.m. - 10:31 a.m.YWG-ORD
14h 16m2 stops
Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
C$ 292
Find Deal
Sun, 28 Sep - Sat, 4 Oct
WestJet Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
WestJet Logo
2:20 p.m. - 8:35 a.m.ORD-YWG
18h 15m2 stops
C$ 303WestJet
Find Deal
Fri, 14 Nov - Mon, 17 Nov
Delta Logo
8:00 a.m. - 1:08 p.m.YWG-MDW
5h 08m1 stop
Delta Logo
11:10 a.m. - 11:27 p.m.MDW-YWG
12h 17m2 stops
C$ 472Delta
Find Deal
Wed, 8 Oct - Sat, 11 Oct
Delta Logo
12:44 p.m. - 10:16 p.m.YWG-MDW
9h 32m2 stops
Delta Logo
9:30 a.m. - 11:33 p.m.MDW-YWG
14h 03m2 stops
C$ 589Delta
Find Deal
Thu, 25 Dec - Tue, 13 Jan
Delta Logo
5:56 p.m. - 11:06 a.m.YWG-MDW
17h 10m1 stop
Delta Logo
9:30 a.m. - 11:33 p.m.MDW-YWG
14h 03m2 stops
C$ 616Delta
Find Deal
Mon, 22 Dec - Tue, 13 Jan

WestJet flights from Manitoba to Chicago

Our best WestJet deals on Manitoba to Chicago flight tickets
WestJet
14 Nov
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
17 Nov
ORD2:20 p.m.Chicago O'Hare Intl
10h 21m
1 stop
YWG12:41 a.m.Winnipeg
C$ 266
Find similar
WestJet
2 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
6 Oct
ORD5:30 p.m.Chicago O'Hare Intl
15h 31m
1 stop
YWG9:01 a.m.Winnipeg
C$ 274
Find similar
WestJet
2 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
5 Oct
ORD5:30 p.m.Chicago O'Hare Intl
15h 31m
1 stop
YWG9:01 a.m.Winnipeg
C$ 276
Find similar

United Airlines flights from Manitoba to Chicago

Our best United Airlines deals on Manitoba to Chicago flight tickets
United Airlines
18 Sep
YWG7:00 a.m.Winnipeg
2h 31m
ORD9:31 a.m.Chicago O'Hare Intl
21 Sep
ORD1:01 p.m.Chicago O'Hare Intl
2h 30m
YWG3:31 p.m.Winnipeg
C$ 979
Find similar
United Airlines
18 Sep
YWG7:00 a.m.Winnipeg
2h 31m
ORD9:31 a.m.Chicago O'Hare Intl
21 Sep
ORD5:00 a.m.Chicago O'Hare Intl
8h 09m
1 stop
YWG1:09 p.m.Winnipeg
C$ 992
Find similar
United Airlines
18 Sep
YWG4:25 p.m.Winnipeg
7h 34m
1 stop
ORD11:59 p.m.Chicago O'Hare Intl
21 Sep
ORD5:00 a.m.Chicago O'Hare Intl
8h 09m
1 stop
YWG1:09 p.m.Winnipeg
C$ 1,014
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Manitoba to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 11 September 2025.
Use the filters below to find and compare flights from Manitoba to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 14/11

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

1 stop7h 20m

Chicago O'Hare Intl

Mon 17/11

2:20 p.m.-12:41 a.m.

1 stop10h 21m

C$ 266

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 2/10

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

1 stop8h 13m

Chicago O'Hare Intl

Mon 6/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 274

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 2/10

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

1 stop8h 13m

Chicago O'Hare Intl

Sun 5/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 276

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 2/10

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

1 stop8h 13m

Chicago O'Hare Intl

Mon 6/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

C$ 280

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 2/10

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

1 stop8h 13m

Chicago O'Hare Intl

Sun 5/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

C$ 287

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 28/9

8:15 p.m.-10:31 a.m.

2 stops14h 16m

Chicago O'Hare Intl

Sat 4/10

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 292

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 14/11

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

1 stop7h 20m

Chicago O'Hare Intl

Mon 17/11

2:20 p.m.-8:35 a.m.

2 stops18h 15m

C$ 303

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/10

8:00 a.m.-1:08 p.m.

1 stop5h 08m

Chicago Midway

Sat 11/10

11:10 a.m.-11:27 p.m.

2 stops12h 17m

C$ 472

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 25/12

12:44 p.m.-10:16 p.m.

2 stops9h 32m

Chicago Midway

Tue 13/1

9:30 a.m.-11:33 p.m.

2 stops14h 03m

C$ 589

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 22/12

5:56 p.m.-11:06 a.m.

1 stop17h 10m

Chicago Midway

Tue 13/1

9:30 a.m.-11:33 p.m.

2 stops14h 03m

C$ 616

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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$ 560.

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$ 802. 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$ 980. 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$ 710. 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$ 869 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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Manitoba when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 620 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Manitoba for as low as C$ 338 on momondo.

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 58% 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$ 587

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Manitoba in the past 72 hours is C$ 587. The best round-trip flight deal from Manitoba to Chicago found on momondo in the last 72 hours is C$ 546.
The fastest flight from Manitoba to Chicago takes 2h 21m
Direct flights go from Manitoba to Chicago every day.
There is 1 airport near Chicago: 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?

  • 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?

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
WestJetPriceFrom C$ 200Free CancellationRating
7.2
3,091 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 362Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 487Free CancellationRating
7.4
8,937 reviews
Search United Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport