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Cheap flights from Winnipeg to Illinois from $123

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 1/12. 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:00 pm - 4:52 pm
YWG
-
ORD
19h 52m2 stops
Multiple Airlines Logo
2:53 pm - 3:07 pm
ORD
-
YWG
24h 14m1 stop
$206Multiple Airlines
Tue, Jan 13 - Tue, Jan 20
Multiple Airlines Logo
12:55 pm - 11:47 am
YWG
-
MDW
22h 52m2 stops
Multiple Airlines Logo
12:57 pm - 12:43 am
MDW
-
YWG
11h 46m1 stop
$210Multiple Airlines
Wed, Jan 14 - Mon, Jan 19
WestJet Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m1 stop
WestJet Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m1 stop
$214WestJet
Fri, Jan 30 - Fri, Feb 6
Multiple Airlines Logo
7:30 am - 4:52 pm
YWG
-
ORD
9h 22m1 stop
Multiple Airlines Logo
11:48 am - 12:43 am
ORD
-
YWG
12h 55m1 stop
$218Multiple Airlines
Wed, Jan 14 - Mon, Jan 19
Multiple Airlines Logo
9:00 pm - 4:52 pm
YWG
-
ORD
19h 52m2 stops
Multiple Airlines Logo
2:53 pm - 3:07 pm
ORD
-
YWG
24h 14m1 stop
$221Multiple Airlines
Tue, Jan 13 - Tue, Jan 20
Multiple Airlines Logo
5:05 pm - 4:52 pm
YWG
-
ORD
23h 47m1 stop
Multiple Airlines Logo
8:41 pm - 12:43 am
ORD
-
YWG
28h 02m1 stop
$232Multiple Airlines
Fri, Jan 16 - Sun, Jan 18
WestJet Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m1 stop
WestJet Logo
2:20 pm - 12:41 am
ORD
-
YWG
10h 21m1 stop
$237WestJet
Mon, Jan 12 - Mon, Jan 19
Delta Logo
6:40 am - 2:38 pm
YWG
-
STL
7h 58m1 stop
Delta Logo
6:10 am - 11:03 am
STL
-
YWG
4h 53m1 stop
$353Delta
Thu, Jan 29 - Mon, Feb 2
Delta Logo
5:21 pm - 11:25 pm
YWG
-
STL
6h 04m1 stop
Delta Logo
6:10 am - 11:03 am
STL
-
YWG
4h 53m1 stop
$361Delta
Thu, Jan 29 - Mon, Feb 2
Air Canada Logo
5:30 am - 2:30 pm
YWG
-
STL
9h 00m2 stops
Air Canada Logo
11:20 am - 11:54 pm
STL
-
YWG
12h 34m2 stops
$420Air Canada
Thu, Jan 29 - Mon, Feb 2

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets
WestJet
Jan 30
YWG6:15 amWinnipeg
7h 20m
1 stop
ORD1:35 pmChicago O'Hare Intl
Feb 6
ORD2:20 pmChicago O'Hare Intl
8h 20m
1 stop
YWG10:40 pmWinnipeg
$214
Find similar
WestJet
Apr 25
YWG12:40 pmWinnipeg
28h 03m
1 stop
ORD4:43 pmChicago O'Hare Intl
Apr 30
ORD5:30 pmChicago O'Hare Intl
24h 10m
1 stop
YWG5:40 pmWinnipeg
$234
Find similar
WestJet
Apr 25
YWG5:00 pmWinnipeg
23h 43m
2 stops
ORD4:43 pmChicago O'Hare Intl
Apr 30
ORD5:30 pmChicago O'Hare Intl
21h 00m
1 stop
YWG2:30 pmWinnipeg
$239
Find similar

Porter Airlines flights from Winnipeg to Illinois

Our best Porter Airlines deals on Winnipeg to Illinois flight tickets
Porter Airlines
Apr 14
YWG6:00 amWinnipeg
8h 05m
1 stop
ORD2:05 pmChicago O'Hare Intl
Apr 18
ORD8:00 amChicago O'Hare Intl
7h 30m
1 stop
YWG3:30 pmWinnipeg
$417
Find similar
Porter Airlines
Apr 14
YWG6:00 amWinnipeg
8h 05m
1 stop
ORD2:05 pmChicago O'Hare Intl
Apr 18
ORD8:00 amChicago O'Hare Intl
7h 30m
1 stop
YWG3:30 pmWinnipeg
$425
Find similar
Porter Airlines
Feb 26
YWG12:10 pmWinnipeg
7h 19m
1 stop
ORD7:29 pmChicago O'Hare Intl
Mar 1
ORD6:40 pmChicago O'Hare Intl
16h 33m
2 stops
YWG11:13 amWinnipeg
$460
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 December 18, 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

Tue 1/13

9:00 pm-4:52 pm

2 stops19h 52m

Chicago O'Hare Intl

Tue 1/20

2:53 pm-3:07 pm

1 stop24h 14m

$206

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 1/14

12:55 pm-11:47 am

2 stops22h 52m

Chicago Midway

Mon 1/19

12:57 pm-12:43 am

1 stop11h 46m

$210

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 1/30

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Fri 2/6

2:20 pm-10:40 pm

1 stop8h 20m

$214

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 1/14

7:30 am-4:52 pm

1 stop9h 22m

Chicago O'Hare Intl

Mon 1/19

11:48 am-12:43 am

1 stop12h 55m

$218

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 1/13

9:00 pm-4:52 pm

2 stops19h 52m

Chicago O'Hare Intl

Tue 1/20

2:53 pm-3:07 pm

1 stop24h 14m

$221

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 1/16

5:05 pm-4:52 pm

1 stop23h 47m

Chicago O'Hare Intl

Sun 1/18

8:41 pm-12:43 am

1 stop28h 02m

$232

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 1/12

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 1/19

2:20 pm-12:41 am

1 stop10h 21m

$237

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Thu 1/29

6:40 am-2:38 pm

1 stop7h 58m

Lambert-St Louis

Mon 2/2

6:10 am-11:03 am

1 stop4h 53m

$353

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Thu 1/29

5:21 pm-11:25 pm

1 stop6h 04m

Lambert-St Louis

Mon 2/2

6:10 am-11:03 am

1 stop4h 53m

$361

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Thu 1/29

5:30 am-2:30 pm

2 stops9h 00m

Lambert-St Louis

Mon 2/2

11:20 am-11:54 pm

2 stops12h 34m

$420

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 $354, 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 $358.

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

The cheapest day to depart from Winnipeg to Illinois is on a Thursday 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 $836. 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 $616.

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?

You could potentially save up to 71% on your flight if you consider stops on a Winnipeg to Illinois flight.

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

$362

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Winnipeg in the past 72 hours is $362. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is $384.
The fastest flight from Winnipeg to Illinois takes 2h 21m
Direct flights go from Winnipeg to Illinois every day.
There are 98 airports in Illinois. From Winnipeg there are direct flights to 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
9,091 reviews
Search United Airlines 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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