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Cheap flights from Manitoba to Chicago from C$ 196

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 30/1. 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:00 p.m. - 7:42 p.m.YWG-MDW
22h 42m2 stops
Multiple Airlines Logo
6:15 a.m. - 3:07 p.m.MDW-YWG
8h 52m1 stop
C$ 293Multiple Airlines
Find Deal
Thu, 4 Dec - Sun, 7 Dec
Multiple Airlines Logo
9:00 p.m. - 10:12 p.m.YWG-MDW
25h 12m2 stops
Multiple Airlines Logo
6:15 a.m. - 3:07 p.m.MDW-YWG
8h 52m1 stop
C$ 304Multiple Airlines
Find Deal
Thu, 4 Dec - Sun, 7 Dec
Multiple Airlines Logo
7:30 a.m. - 12:08 a.m.YWG-ORD
16h 38m1 stop
Multiple Airlines Logo
11:44 a.m. - 6:06 p.m.ORD-YWG
30h 22m2 stops
C$ 308Multiple Airlines
Find Deal
Wed, 26 Nov - Mon, 8 Dec
Multiple Airlines Logo
7:30 a.m. - 12:08 a.m.YWG-ORD
16h 38m1 stop
Multiple Airlines Logo
4:22 p.m. - 3:07 p.m.ORD-YWG
22h 45m1 stop
C$ 315Multiple Airlines
Find Deal
Wed, 26 Nov - Tue, 9 Dec
WestJet Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
WestJet Logo
2:20 p.m. - 10:41 p.m.ORD-YWG
8h 21m1 stop
C$ 333WestJet
Find Deal
Fri, 16 Jan - Mon, 19 Jan
WestJet Logo
9:00 p.m. - 1:35 p.m.YWG-ORD
16h 35m1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.ORD-YWG
8h 20m1 stop
C$ 375WestJet
Find Deal
Thu, 12 Feb - Mon, 16 Feb
Delta Logo
11:53 a.m. - 6:37 p.m.YWG-MDW
6h 44m1 stop
Delta Logo
6:00 a.m. - 3:09 p.m.MDW-YWG
9h 09m1 stop
C$ 768Delta
Find Deal
Tue, 3 Mar - Sun, 8 Mar
Delta Logo
12:35 p.m. - 11:47 p.m.YWG-MDW
11h 12m2 stops
Delta Logo
9:34 a.m. - 7:12 p.m.MDW-YWG
9h 38m2 stops
C$ 845Delta
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Thu, 4 Dec - Sun, 7 Dec
Porter Airlines Logo
4:25 p.m. - 10:05 a.m.YWG-MDW
17h 40m2 stops
Porter Airlines Logo
11:00 a.m. - 11:08 a.m.MDW-YWG
24h 08m2 stops
C$ 1,091Porter Airlines
Find Deal
Mon, 17 Nov - Thu, 20 Nov
Porter Airlines Logo
4:25 p.m. - 10:05 a.m.YWG-MDW
17h 40m2 stops
Porter Airlines Logo
11:00 a.m. - 11:08 a.m.MDW-YWG
24h 08m3 stops
C$ 1,220Porter Airlines
Find Deal
Mon, 17 Nov - Thu, 20 Nov

WestJet flights from Manitoba to Chicago

Our best WestJet deals on Manitoba to Chicago flight tickets
WestJet
16 Jan
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
19 Jan
ORD2:20 p.m.Chicago O'Hare Intl
8h 21m
1 stop
YWG10:41 p.m.Winnipeg
C$ 333
Find similar
WestJet
12 Feb
YWG9:00 p.m.Winnipeg
16h 35m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
16 Feb
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
C$ 375
Find similar
WestJet
28 Nov
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
5 Dec
ORD2:20 p.m.Chicago O'Hare Intl
8h 21m
1 stop
YWG10:41 p.m.Winnipeg
C$ 422
Find similar

Air Canada flights from Manitoba to Chicago

Our best Air Canada deals on Manitoba to Chicago flight tickets
Air Canada
6 Nov
YWG2:20 p.m.Winnipeg
2h 41m
ORD5:01 p.m.Chicago O'Hare Intl
15 Nov
ORD9:22 a.m.Chicago O'Hare Intl
2h 35m
YWG11:57 a.m.Winnipeg
C$ 1,237
Find similar
Air Canada
7 Nov
YWG8:40 a.m.Winnipeg
10h 13m
1 stop
ORD6:53 p.m.Chicago O'Hare Intl
15 Nov
ORD9:22 a.m.Chicago O'Hare Intl
2h 35m
YWG11:57 a.m.Winnipeg
C$ 1,245
Find similar
Air Canada
7 Nov
YWG8:40 a.m.Winnipeg
10h 13m
1 stop
ORD6:53 p.m.Chicago O'Hare Intl
15 Nov
ORD7:05 a.m.Chicago O'Hare Intl
9h 30m
1 stop
YWG4:35 p.m.Winnipeg
C$ 1,308
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 3 November 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 - MDW

YWGMDW

Winnipeg

Thu 4/12

9:00 p.m.-7:42 p.m.

2 stops22h 42m

Chicago Midway

Sun 7/12

6:15 a.m.-3:07 p.m.

1 stop8h 52m

C$ 293

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 4/12

9:00 p.m.-10:12 p.m.

2 stops25h 12m

Chicago Midway

Sun 7/12

6:15 a.m.-3:07 p.m.

1 stop8h 52m

C$ 304

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 26/11

7:30 a.m.-12:08 a.m.

1 stop16h 38m

Chicago O'Hare Intl

Mon 8/12

11:44 a.m.-6:06 p.m.

2 stops30h 22m

C$ 308

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 26/11

7:30 a.m.-12:08 a.m.

1 stop16h 38m

Chicago O'Hare Intl

Tue 9/12

4:22 p.m.-3:07 p.m.

1 stop22h 45m

C$ 315

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 16/1

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

1 stop7h 20m

Chicago O'Hare Intl

Mon 19/1

2:20 p.m.-10:41 p.m.

1 stop8h 21m

C$ 333

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 12/2

9:00 p.m.-1:35 p.m.

1 stop16h 35m

Chicago O'Hare Intl

Mon 16/2

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

1 stop8h 20m

C$ 375

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

11:53 a.m.-6:37 p.m.

1 stop6h 44m

Chicago Midway

Sun 8/3

6:00 a.m.-3:09 p.m.

1 stop9h 09m

C$ 768

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 4/12

12:35 p.m.-11:47 p.m.

2 stops11h 12m

Chicago Midway

Sun 7/12

9:34 a.m.-7:12 p.m.

2 stops9h 38m

C$ 845

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 17/11

4:25 p.m.-10:05 a.m.

2 stops17h 40m

Chicago Midway

Thu 20/11

11:00 a.m.-11:08 a.m.

2 stops24h 08m

C$ 1,091

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 17/11

4:25 p.m.-10:05 a.m.

2 stops17h 40m

Chicago Midway

Thu 20/11

11:00 a.m.-11:08 a.m.

3 stops24h 08m

C$ 1,220

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$ 523.

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$ 808. 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$ 718. 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$ 883 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 3 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 59% 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$ 269

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$ 269. The best round-trip flight deal from Manitoba to Chicago found on momondo in the last 72 hours is C$ 637.
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$ 203Free CancellationRating
7.2
3,153 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 384Free CancellationRating
7.1
10,398 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 493Free CancellationRating
7.4
8,997 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