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Cheap flights from Manitoba to Chicago from C$ 245

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 26/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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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.
WestJet Logo
6:00 a.m. - 4:40 p.m.
YWG
-
ORD
10h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 316WestJet
Sat, 23 May - Sat, 30 May
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 373WestJet
Wed, 10 Jun - Mon, 15 Jun
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 384WestJet
Sat, 5 Sep - Tue, 8 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 395WestJet
Sat, 5 Sep - Tue, 8 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 419WestJet
Fri, 25 Sep - Sun, 27 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 448WestJet
Fri, 21 Aug - Mon, 24 Aug
Multiple Airlines Logo
8:45 p.m. - 9:35 a.m.
YWG
-
MDW
12h 50m
1 stop
Multiple Airlines Logo
3:20 p.m. - 9:45 a.m.
MDW
-
YWG
18h 25m
1 stop
C$ 593Multiple Airlines
Mon, 1 Jun - Mon, 8 Jun
Delta Logo
6:40 a.m. - 6:31 p.m.
YWG
-
MDW
11h 51m
2 stops
Delta Logo
6:58 p.m. - 3:04 p.m.
MDW
-
YWG
20h 06m
2 stops
C$ 712Delta
Tue, 23 Jun - Tue, 30 Jun
Delta Logo
6:40 a.m. - 9:46 p.m.
YWG
-
MDW
15h 06m
2 stops
Delta Logo
6:00 a.m. - 8:09 p.m.
MDW
-
YWG
14h 09m
2 stops
C$ 724Delta
Wed, 23 Sep - Sat, 26 Sep
Delta Logo
5:41 p.m. - 8:43 a.m.
YWG
-
MDW
15h 02m
2 stops
Delta Logo
5:12 p.m. - 2:55 p.m.
MDW
-
YWG
21h 43m
2 stops
C$ 732Delta
Sat, 23 May - Wed, 27 May

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Porter Airlines flights from Manitoba to Chicago

Our best Porter Airlines deals on Manitoba to Chicago flight tickets
Porter Airlines
7 Oct
YWG9:20 a.m.Winnipeg
6h 35m
1 stop
ORD3:55 p.m.Chicago O'Hare Intl
21 Oct
ORD7:00 a.m.Chicago O'Hare Intl
10h 58m
2 stops
YWG5:58 p.m.Winnipeg
C$ 649
Porter Airlines
13 May
YWG4:15 p.m.Winnipeg
17h 30m
2 stops
MDW9:45 a.m.Chicago Midway
8 Jun
MDW10:15 a.m.Chicago Midway
7h 43m
2 stops
YWG5:58 p.m.Winnipeg
C$ 980

WestJet flights from Manitoba to Chicago

Our best WestJet deals on Manitoba to Chicago flight tickets
WestJet
23 May
YWG6:00 a.m.Winnipeg
10h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
30 May
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 316
WestJet
10 Jun
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
15 Jun
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 373
WestJet
5 Sep
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
8 Sep
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 384

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 7 May 2026.
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

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 23/5

6:00 a.m.-4:40 p.m.

1 stop10h 40m

Chicago O'Hare Intl

Sat 30/5

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

1 stop7h 25m

C$ 316
Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 10/6

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 15/6

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

1 stop7h 25m

C$ 373

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 5/9

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

1 stop9h 40m

Chicago O'Hare Intl

Tue 8/9

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

1 stop7h 25m

C$ 384

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 5/9

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

1 stop9h 40m

Chicago O'Hare Intl

Tue 8/9

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

1 stop7h 25m

C$ 395

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 25/9

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

1 stop9h 40m

Chicago O'Hare Intl

Sun 27/9

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

1 stop7h 25m

C$ 419

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 21/8

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 24/8

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

1 stop7h 25m

C$ 448

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 1/6

8:45 p.m.-9:35 a.m.

1 stop12h 50m

Chicago Midway

Mon 8/6

3:20 p.m.-9:45 a.m.

1 stop18h 25m

C$ 593

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 23/6

6:40 a.m.-6:31 p.m.

2 stops11h 51m

Chicago Midway

Tue 30/6

6:58 p.m.-3:04 p.m.

2 stops20h 06m

C$ 712

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 23/9

6:40 a.m.-9:46 p.m.

2 stops15h 06m

Chicago Midway

Sat 26/9

6:00 a.m.-8:09 p.m.

2 stops14h 09m

C$ 724

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 23/5

5:41 p.m.-8:43 a.m.

2 stops15h 02m

Chicago Midway

Wed 27/5

5:12 p.m.-2:55 p.m.

2 stops21h 43m

C$ 732

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 May is another great option to travel to Chicago, with average flight prices from Manitoba averaging around C$ 122.

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 Friday when prices can be found for as low as C$ 768. 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 Monday because tickets tend to average around C$ 1,065. 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 morning is the cheapest time of day to fly from Manitoba to Chicago when you can find flight prices for as low as C$ 821. Flying to Chicago in the morning 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$ 941 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

Can stopping save me money on Manitoba to Chicago flights?

You could potentially save up to 42% 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$ 396

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Manitoba in the past 72 hours is C$ 396. The best round-trip flight deal from Manitoba to Chicago found on momondo in the last 72 hours is C$ 593.
The fastest flight from Manitoba to Chicago takes 2h 21m
Direct flights go from Manitoba to Chicago every day.
There are 3 airports in Chicago. From Manitoba there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Manitoba to Chicago

  • 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$ 266Free CancellationRating
7.2
3,331 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 359Free CancellationRating
7.1
11,004 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 474Free CancellationRating
7.4
9,690 reviews
Search United Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster

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