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Cheap flights from Winnipeg to Illinois from $126

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Illinois departing on 10/31. 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
0 bags

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Find the cheapest flights from Winnipeg to Illinois

Cheap round-trip flights

WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 9:01 amORD-YWG
15h 31m1 stop
$195WestJet
Find Deal
Sun, Oct 12 - Sun, Oct 19
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 9:01 amORD-YWG
15h 31m1 stop
$204WestJet
Find Deal
Fri, Oct 17 - Sun, Oct 19
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 11:26 amORD-YWG
17h 56m2 stops
$217WestJet
Find Deal
Fri, Oct 17 - Sun, Oct 19
Multiple Airlines Logo
9:00 pm - 6:39 pmYWG-MDW
21h 39m2 stops
Multiple Airlines Logo
1:37 pm - 3:07 pmMDW-YWG
25h 30m1 stop
$218Multiple Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Multiple Airlines Logo
7:30 am - 6:39 pmYWG-MDW
11h 09m1 stop
Multiple Airlines Logo
5:20 am - 2:07 pmMDW-YWG
8h 47m1 stop
$231Multiple Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2
United Airlines Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
United Airlines Logo
5:01 am - 1:09 pmORD-YWG
8h 08m1 stop
$341United Airlines
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Thu, Oct 16 - Sun, Oct 19
United Airlines Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
United Airlines Logo
1:01 pm - 3:31 pmORD-YWG
2h 30mnonstop
$342United Airlines
Find Deal
Thu, Oct 9 - Sun, Oct 12
Delta Logo
6:40 am - 1:08 pmYWG-MDW
6h 28m1 stop
Delta Logo
9:20 am - 4:50 pmMDW-YWG
7h 30m1 stop
$447Delta
Find Deal
Thu, Oct 9 - Sun, Oct 12
Delta Logo
12:40 pm - 6:08 pmYWG-MDW
5h 28m1 stop
Delta Logo
6:00 am - 3:09 pmMDW-YWG
9h 09m1 stop
$553Delta
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Tue, Mar 3 - Sun, Mar 8
Porter Airlines Logo
4:25 pm - 11:50 amYWG-MDW
19h 25m2 stops
Porter Airlines Logo
11:00 am - 11:13 amMDW-YWG
24h 13m2 stops
$796Porter Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets
WestJet
Oct 12
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 19
ORD5:30 pmChicago O'Hare Intl
15h 31m
1 stop
YWG9:01 amWinnipeg
$195
Find similar
WestJet
Oct 17
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 19
ORD5:30 pmChicago O'Hare Intl
15h 31m
1 stop
YWG9:01 amWinnipeg
$204
Find similar
WestJet
Oct 17
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 19
ORD5:30 pmChicago O'Hare Intl
17h 56m
2 stops
YWG11:26 amWinnipeg
$217
Find similar

United Airlines flights from Winnipeg to Illinois

Our best United Airlines deals on Winnipeg to Illinois flight tickets
United Airlines
Oct 16
YWG7:00 amWinnipeg
2h 31m
ORD9:31 amChicago O'Hare Intl
Oct 19
ORD5:01 amChicago O'Hare Intl
8h 08m
1 stop
YWG1:09 pmWinnipeg
$341
Find similar
United Airlines
Oct 9
YWG2:20 pmWinnipeg
2h 31m
ORD4:51 pmChicago O'Hare Intl
Oct 12
ORD1:01 pmChicago O'Hare Intl
2h 30m
YWG3:31 pmWinnipeg
$342
Find similar
United Airlines
Oct 9
YWG2:20 pmWinnipeg
2h 31m
ORD4:51 pmChicago O'Hare Intl
Oct 12
ORD5:01 amChicago O'Hare Intl
8h 08m
1 stop
YWG1:09 pmWinnipeg
$343
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg 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 832,500 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Winnipeg to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 10/12

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-9:01 am

1 stop15h 31m

$195

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/17

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-9:01 am

1 stop15h 31m

$204

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/17

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-11:26 am

2 stops17h 56m

$217

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/30

9:00 pm-6:39 pm

2 stops21h 39m

Chicago Midway

Thu 11/6

1:37 pm-3:07 pm

1 stop25h 30m

$218

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/31

7:30 am-6:39 pm

1 stop11h 09m

Chicago Midway

Sun 11/2

5:20 am-2:07 pm

1 stop8h 47m

$231

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/16

7:00 am-9:31 am

Nonstop2h 31m

Chicago O'Hare Intl

Sun 10/19

5:01 am-1:09 pm

1 stop8h 08m

$341

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/9

2:20 pm-4:51 pm

Nonstop2h 31m

Chicago O'Hare Intl

Sun 10/12

1:01 pm-3:31 pm

Nonstop2h 30m

$342

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/9

6:40 am-1:08 pm

1 stop6h 28m

Chicago Midway

Sun 10/12

9:20 am-4:50 pm

1 stop7h 30m

$447

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

12:40 pm-6:08 pm

1 stop5h 28m

Chicago Midway

Sun 3/8

6:00 am-3:09 pm

1 stop9h 09m

$553

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/31

4:25 pm-11:50 am

2 stops19h 25m

Chicago Midway

Sun 11/2

11:00 am-11:13 am

2 stops24h 13m

$796

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 Winnipeg 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?

The cheapest month to fly to Illinois from Winnipeg is in September. Flight prices, which tend to average around $363, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of September, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $399.

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

The cheapest day to depart from Winnipeg to Illinois is on a Friday when prices can be found for as low as $533. Flights from Winnipeg to Illinois on a Sunday will generally be more expensive and average around $799. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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 Winnipeg to Illinois during this time can be as low as $440. Flights at noon are often more expensive with an average ticket price of $634.

What is the cheapest Winnipeg to Illinois flight route?

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

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

There are 4 cabin classes available to choose from on Winnipeg 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 Winnipeg to Illinois flights?

No. A direct flight is the cheapest option for a flight between Winnipeg to Illinois.

Cheap Winnipeg to Illinois flight deals and tips

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

Best Price Found

$247

Fastest flight time

2h 21m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Illinois

1 airport
The best one-way flight to Illinois from Winnipeg in the past 72 hours is $247. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is $466.
The fastest flight from Winnipeg to Illinois takes 2h 21m
Direct flights go from Winnipeg to Illinois on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Illinois: Chicago O'Hare Intl (ORD)
Search flight deals

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

    Prices for flights from Winnipeg Airport to Illinois refresh daily.

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

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

    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 Winnipeg Airport to Illinois.

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

    The travel and health documents required for your trip to Illinois 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 Illinois. 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 Winnipeg to Illinois?

Best airlines flying from Winnipeg to Illinois

Compare and see reviews for airlines that fly from Winnipeg to Illinois with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $199Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
Air CanadaPriceFrom $230Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

Why use momondo?

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

It is quick and easy to find Winnipeg to Illinois flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Illinois that suits you.

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

Yes. momondo enables you to select and highlight flights to Illinois from Winnipeg with this policy.

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

Once all potential Winnipeg to Illinois flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from Winnipeg 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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