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Cheap flights from Manitoba to Illinois 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 Illinois 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 Illinois

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
4:22 p.m. - 6:06 p.m.ORD-YWG
25h 44m2 stops
C$ 308Multiple Airlines
Find Deal
Wed, 26 Nov - Tue, 9 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
Find Deal
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 Illinois

Our best WestJet deals on Manitoba to Illinois 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 Illinois

Our best Air Canada deals on Manitoba to Illinois 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 Illinois 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 Illinois 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

Tue 9/12

4:22 p.m.-6:06 p.m.

2 stops25h 44m

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 Illinois from

How to get the cheapest flight ticket from Manitoba to Illinois

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 Illinois?

In general, September is the cheapest month to fly from Manitoba to Illinois. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 496. If you don’t want to visit Illinois in September, then you should wait until October to fly from Manitoba, when ticket prices are also cheap, with an average price of C$ 523.

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

According to our data, Wednesday is the cheapest day to fly to Illinois from Manitoba. The lowest ticket price found for a Wednesday departure recently was C$ 808. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to Illinois is Sunday, with ticket prices averaging around C$ 1,006.

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

Our most recent data shows that the best time of day to fly to Illinois is in the afternoon. Flights from Manitoba to Illinois during this time can be as low as C$ 718. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 883 on average. Flights to Illinois from Manitoba at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

What is the cheapest Manitoba to Illinois flight route?

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

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

There are 3 cabin classes available to choose from on Manitoba to Illinois 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 Illinois flights?

You could potentially save up to 59% on your flight if you consider stops on a Manitoba to Illinois flight.

Cheap Manitoba to Illinois flight deals and tips

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

Best price found

C$ 269

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Illinois

1 airport
The best one-way flight to Illinois from Manitoba in the past 72 hours is C$ 269. The best round-trip flight deal from Manitoba to Illinois found on momondo in the last 72 hours is C$ 637.
The fastest flight from Manitoba to Illinois takes 2h 21m
Direct flights go from Manitoba to Illinois every day.
There is 1 airport near Illinois: Chicago O'Hare Intl (ORD)
Search flight deals

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

    Prices for flights from Manitoba to Illinois were last updated today.

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

  • How old do you have to be to fly from Manitoba to Illinois?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Manitoba to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The required travel and health documents for your Illinois trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Illinois. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Manitoba to Illinois?

Best airlines flying from Manitoba to Illinois

Compare and see reviews for airlines that fly from Manitoba to Illinois 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

Why use momondo?

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

Finding the right flight to Illinois from Manitoba is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Illinois quick and easy, saving you time and money.

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

Flights from Manitoba to Illinois with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Manitoba to Illinois.

I’m not ready to book a flight from Manitoba to Illinois right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Manitoba to Illinois now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Illinois and let you know when they change.

An easier way to manage your Illinois 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 Illinois

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