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Cheap flights from Manitoba to Chicago from C$ 276

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 22/3. 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
4:55 p.m. - 4:40 p.m.
YWG
-
ORD
23h 45m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 498WestJet
Mon, 15 Jun - Fri, 19 Jun
Multiple Airlines Logo
8:00 a.m. - 6:08 a.m.
YWG
-
ORD
22h 08m
1 stop
Multiple Airlines Logo
7:31 p.m. - 3:30 p.m.
ORD
-
YWG
19h 59m
2 stops
C$ 531Multiple Airlines
Mon, 23 Mar - Mon, 30 Mar
Multiple Airlines Logo
11:55 a.m. - 6:36 p.m.
YWG
-
MDW
6h 41m
1 stop
Multiple Airlines Logo
6:00 a.m. - 10:10 p.m.
MDW
-
YWG
16h 10m
2 stops
C$ 559Multiple Airlines
Tue, 28 Apr - Wed, 29 Apr
Multiple Airlines Logo
11:55 a.m. - 6:13 p.m.
YWG
-
ORD
6h 18m
1 stop
Multiple Airlines Logo
5:01 a.m. - 10:10 p.m.
ORD
-
YWG
17h 09m
2 stops
C$ 559Multiple Airlines
Tue, 28 Apr - Wed, 29 Apr
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
Multiple Airlines Logo
8:53 p.m. - 5:40 p.m.
ORD
-
YWG
20h 47m
2 stops
C$ 566Multiple Airlines
Tue, 16 Jun - Mon, 22 Jun
Multiple Airlines Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m
1 stop
Multiple Airlines Logo
7:30 a.m. - 9:13 p.m.
ORD
-
YWG
13h 43m
2 stops
C$ 567Multiple Airlines
Fri, 20 Mar - Sun, 22 Mar
WestJet Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m
1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
C$ 607WestJet
Mon, 23 Mar - Mon, 30 Mar
Multiple Airlines Logo
12:10 p.m. - 11:17 a.m.
YWG
-
ORD
23h 07m
2 stops
Multiple Airlines Logo
7:31 p.m. - 7:35 p.m.
ORD
-
YWG
24h 04m
2 stops
C$ 614Multiple Airlines
Mon, 23 Mar - Mon, 30 Mar
Multiple Airlines Logo
12:10 p.m. - 5:31 a.m.
YWG
-
ORD
17h 21m
2 stops
Multiple Airlines Logo
6:34 p.m. - 10:10 p.m.
ORD
-
YWG
27h 36m
3 stops
C$ 617Multiple Airlines
Tue, 28 Apr - Wed, 29 Apr
WestJet Logo
10:45 a.m. - 6:41 p.m.
YWG
-
ORD
7h 56m
2 stops
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 619WestJet
Mon, 15 Jun - Fri, 19 Jun

United Airlines flights from Manitoba to Chicago

Our best United Airlines deals on Manitoba to Chicago flight tickets
United Airlines
23 Mar
YWG2:20 p.m.Winnipeg
2h 25m
ORD4:45 p.m.Chicago O'Hare Intl
30 Mar
ORD9:18 a.m.Chicago O'Hare Intl
2h 34m
YWG11:52 a.m.Winnipeg
C$ 764
United Airlines
12 Mar
YWG2:20 p.m.Winnipeg
2h 25m
ORD4:45 p.m.Chicago O'Hare Intl
15 Mar
ORD9:15 a.m.Chicago O'Hare Intl
2h 42m
YWG11:57 a.m.Winnipeg
C$ 768
United Airlines
26 Mar
YWG2:20 p.m.Winnipeg
2h 25m
ORD4:45 p.m.Chicago O'Hare Intl
1 Apr
ORD9:18 a.m.Chicago O'Hare Intl
2h 34m
YWG11:52 a.m.Winnipeg
C$ 770

WestJet flights from Manitoba to Chicago

Our best WestJet deals on Manitoba to Chicago flight tickets
WestJet
15 Jun
YWG4:55 p.m.Winnipeg
23h 45m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
19 Jun
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 498
WestJet
23 Mar
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
30 Mar
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
C$ 607
WestJet
15 Jun
YWG10:45 a.m.Winnipeg
7h 56m
2 stops
ORD6:41 p.m.Chicago O'Hare Intl
19 Jun
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 619

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 February 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

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 15/6

4:55 p.m.-4:40 p.m.

1 stop23h 45m

Chicago O'Hare Intl

Fri 19/6

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

1 stop7h 25m

C$ 498

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 23/3

8:00 a.m.-6:08 a.m.

1 stop22h 08m

Chicago O'Hare Intl

Mon 30/3

7:31 p.m.-3:30 p.m.

2 stops19h 59m

C$ 531

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 28/4

11:55 a.m.-6:36 p.m.

1 stop6h 41m

Chicago Midway

Wed 29/4

6:00 a.m.-10:10 p.m.

2 stops16h 10m

C$ 559

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 28/4

11:55 a.m.-6:13 p.m.

1 stop6h 18m

Chicago O'Hare Intl

Wed 29/4

5:01 a.m.-10:10 p.m.

2 stops17h 09m

C$ 559

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 16/6

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 22/6

8:53 p.m.-5:40 p.m.

2 stops20h 47m

C$ 566

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 20/3

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

1 stop7h 20m

Chicago O'Hare Intl

Sun 22/3

7:30 a.m.-9:13 p.m.

2 stops13h 43m

C$ 567

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 23/3

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

1 stop7h 20m

Chicago O'Hare Intl

Mon 30/3

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

1 stop8h 20m

C$ 607

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 23/3

12:10 p.m.-11:17 a.m.

2 stops23h 07m

Chicago O'Hare Intl

Mon 30/3

7:31 p.m.-7:35 p.m.

2 stops24h 04m

C$ 614

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 28/4

12:10 p.m.-5:31 a.m.

2 stops17h 21m

Chicago O'Hare Intl

Wed 29/4

6:34 p.m.-10:10 p.m.

3 stops27h 36m

C$ 617

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 15/6

10:45 a.m.-6:41 p.m.

2 stops7h 56m

Chicago O'Hare Intl

Fri 19/6

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

1 stop7h 25m

C$ 619

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$ 490.

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$ 754. 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$ 1,016. 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$ 835. 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$ 918 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 64% 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$ 261

Fastest flight time

2h 21m

Direct flights

Mon, Tue, Wed, 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$ 261. The best round-trip flight deal from Manitoba to Chicago found on momondo in the last 72 hours is C$ 518.
The fastest flight from Manitoba to Chicago takes 2h 21m
Direct flights go from Manitoba to Chicago on Monday, Tuesday, Wednesday, 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?

  • 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$ 198Free CancellationRating
7.2
3,255 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 357Free CancellationRating
7.1
10,697 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 481Free CancellationRating
7.4
9,245 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

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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