Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Illinois from $182

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 4/23. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Winnipeg to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
9:00 pm - 4:40 pm
YWG
-
ORD
19h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$292WestJet
Sat, Apr 25 - Thu, Apr 30
WestJet Logo
6:55 pm - 4:40 pm
YWG
-
ORD
21h 45m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$293WestJet
Sat, Apr 25 - Thu, Apr 30
WestJet Logo
7:50 am - 1:35 pm
YWG
-
ORD
29h 45m
1 stop
WestJet Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m
1 stop
$294WestJet
Thu, Mar 5 - Mon, Mar 9
WestJet Logo
7:50 am - 1:35 pm
YWG
-
ORD
29h 45m
1 stop
WestJet Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m
1 stop
$295WestJet
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
12:20 pm - 3:52 pm
YWG
-
ORD
27h 32m
2 stops
Multiple Airlines Logo
7:41 pm - 3:09 pm
ORD
-
YWG
19h 28m
1 stop
$341Multiple Airlines
Tue, Mar 3 - Tue, Mar 10
United Airlines Logo
2:20 pm - 9:05 pm
YWG
-
STL
6h 45m
1 stop
United Airlines Logo
6:25 am - 11:57 am
STL
-
YWG
5h 32m
1 stop
$351United Airlines
Tue, Mar 3 - Tue, Mar 10
Delta Logo
11:55 am - 5:05 pm
YWG
-
STL
5h 10m
1 stop
Delta Logo
6:29 am - 11:01 am
STL
-
YWG
4h 32m
1 stop
$352Delta
Wed, Mar 11 - Tue, Mar 17
Multiple Airlines Logo
8:20 pm - 10:05 am
YWG
-
MDW
13h 45m
1 stop
Multiple Airlines Logo
9:51 pm - 7:35 pm
MDW
-
YWG
21h 44m
2 stops
$366Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Delta Logo
6:40 am - 2:54 pm
YWG
-
STL
8h 14m
1 stop
Delta Logo
6:10 am - 11:01 am
STL
-
YWG
4h 51m
1 stop
$394Delta
Sun, Mar 1 - Wed, Mar 4
Air Canada Logo
5:10 am - 12:21 pm
YWG
-
STL
7h 11m
1 stop
Air Canada Logo
8:55 am - 4:20 pm
STL
-
YWG
7h 25m
1 stop
$404Air Canada
Tue, Jun 30 - Tue, Jul 7

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets
WestJet
Apr 25
YWG9:00 pmWinnipeg
19h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Apr 30
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$292
WestJet
Apr 25
YWG6:55 pmWinnipeg
21h 45m
1 stop
ORD4:40 pmChicago O'Hare Intl
Apr 30
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$293
WestJet
Mar 5
YWG7:50 amWinnipeg
29h 45m
1 stop
ORD1:35 pmChicago O'Hare Intl
Mar 9
ORD2:20 pmChicago O'Hare Intl
8h 20m
1 stop
YWG10:40 pmWinnipeg
$294

United Airlines flights from Winnipeg to Illinois

Our best United Airlines deals on Winnipeg to Illinois flight tickets
United Airlines
Mar 3
YWG2:20 pmWinnipeg
6h 45m
1 stop
STL9:05 pmLambert-St Louis
Mar 10
STL6:25 amLambert-St Louis
5h 32m
1 stop
YWG11:57 amWinnipeg
$351
United Airlines
Jun 30
YWG5:10 amWinnipeg
7h 11m
1 stop
STL12:21 pmLambert-St Louis
Jul 7
STL6:00 amLambert-St Louis
10h 20m
2 stops
YWG4:20 pmWinnipeg
$460
United Airlines
Feb 7
YWG2:20 pmWinnipeg
2h 43m
ORD5:03 pmChicago O'Hare Intl
Feb 14
ORD2:00 pmChicago O'Hare Intl
5h 34m
1 stop
YWG7:34 pmWinnipeg
$890

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 February 4, 2026.
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

Sat 4/25

9:00 pm-4:40 pm

1 stop19h 40m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-12:55 am

1 stop7h 25m

$292

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 4/25

6:55 pm-4:40 pm

1 stop21h 45m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-12:55 am

1 stop7h 25m

$293

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 3/5

7:50 am-1:35 pm

1 stop29h 45m

Chicago O'Hare Intl

Mon 3/9

2:20 pm-10:40 pm

1 stop8h 20m

$294

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 3/5

7:50 am-1:35 pm

1 stop29h 45m

Chicago O'Hare Intl

Mon 3/9

2:20 pm-10:40 pm

1 stop8h 20m

$295

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 3/3

12:20 pm-3:52 pm

2 stops27h 32m

Chicago O'Hare Intl

Tue 3/10

7:41 pm-3:09 pm

1 stop19h 28m

$341

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Tue 3/3

2:20 pm-9:05 pm

1 stop6h 45m

Lambert-St Louis

Tue 3/10

6:25 am-11:57 am

1 stop5h 32m

$351

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Wed 3/11

11:55 am-5:05 pm

1 stop5h 10m

Lambert-St Louis

Tue 3/17

6:29 am-11:01 am

1 stop4h 32m

$352

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 3/5

8:20 pm-10:05 am

1 stop13h 45m

Chicago Midway

Mon 3/9

9:51 pm-7:35 pm

2 stops21h 44m

$366

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Sun 3/1

6:40 am-2:54 pm

1 stop8h 14m

Lambert-St Louis

Wed 3/4

6:10 am-11:01 am

1 stop4h 51m

$394

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Tue 6/30

5:10 am-12:21 pm

1 stop7h 11m

Lambert-St Louis

Tue 7/7

8:55 am-4:20 pm

1 stop7h 25m

$404

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 Friday when prices can be found for as low as $494. 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 morning. Flights from Winnipeg to Illinois during this time can be as low as $605. Flights at noon are often more expensive with an average ticket price of $610.

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 68% 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

$218

Fastest flight time

2h 25m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Winnipeg in the past 72 hours is $218. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is $245.
The fastest flight from Winnipeg to Illinois takes 2h 25m
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
9,236 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 3/6
Fri 3/13
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Illinois

Popular cities in Illinois

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $49
Flights to Los Angelesfrom $46
Flights to Miamifrom $27
Flights to Chicagofrom $49
Flights to Orlandofrom $50
Flights to San Franciscofrom $54
Flights to Las Vegasfrom $49
Flights to Washington, D.C.from $51
Flights to Bostonfrom $51
Flights to Atlantafrom $49
Flights to Dallasfrom $49
Flights to Seattlefrom $83