Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Illinois from $140

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 1/30. 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.
Multiple Airlines Logo
9:00 pm - 7:42 pmYWG-MDW
22h 42m2 stops
Multiple Airlines Logo
6:15 am - 3:07 pmMDW-YWG
8h 52m1 stop
$209Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
9:00 pm - 7:42 pmYWG-MDW
22h 42m2 stops
Multiple Airlines Logo
6:15 am - 3:07 pmMDW-YWG
8h 52m1 stop
$216Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
9:00 pm - 10:12 pmYWG-MDW
25h 12m2 stops
Multiple Airlines Logo
6:15 am - 3:07 pmMDW-YWG
8h 52m1 stop
$217Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
WestJet Logo
6:15 am - 1:35 pmYWG-ORD
7h 20m1 stop
WestJet Logo
2:20 pm - 10:41 pmORD-YWG
8h 21m1 stop
$238WestJet
Find Deal
Fri, Jan 16 - Mon, Jan 19
WestJet Logo
9:00 pm - 1:35 pmYWG-ORD
16h 35m1 stop
WestJet Logo
2:20 pm - 10:40 pmORD-YWG
8h 20m1 stop
$268WestJet
Find Deal
Thu, Feb 12 - Mon, Feb 16
United Airlines Logo
8:30 am - 4:26 pmYWG-STL
7h 56m1 stop
United Airlines Logo
1:30 pm - 8:48 pmSTL-YWG
7h 18m1 stop
$348United Airlines
Find Deal
Tue, Apr 14 - Wed, Apr 15
Air Canada Logo
7:15 am - 3:21 pmYWG-STL
8h 06m2 stops
Air Canada Logo
1:30 pm - 8:48 pmSTL-YWG
7h 18m1 stop
$407Air Canada
Find Deal
Tue, Apr 14 - Wed, Apr 15
Air Canada Logo
6:00 am - 3:21 pmYWG-STL
9h 21m2 stops
Air Canada Logo
1:30 pm - 8:48 pmSTL-YWG
7h 18m1 stop
$463Air Canada
Find Deal
Tue, Apr 14 - Wed, Apr 15
Delta Logo
11:53 am - 6:37 pmYWG-MDW
6h 44m1 stop
Delta Logo
6:00 am - 3:09 pmMDW-YWG
9h 09m1 stop
$548Delta
Find Deal
Tue, Mar 3 - Sun, Mar 8
Delta Logo
12:35 pm - 11:47 pmYWG-MDW
11h 12m2 stops
Delta Logo
9:34 am - 7:12 pmMDW-YWG
9h 38m2 stops
$603Delta
Find Deal
Thu, Dec 4 - Sun, Dec 7

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets
WestJet
Jan 16
YWG6:15 amWinnipeg
7h 20m
1 stop
ORD1:35 pmChicago O'Hare Intl
Jan 19
ORD2:20 pmChicago O'Hare Intl
8h 21m
1 stop
YWG10:41 pmWinnipeg
$238
Find similar
WestJet
Feb 12
YWG9:00 pmWinnipeg
16h 35m
1 stop
ORD1:35 pmChicago O'Hare Intl
Feb 16
ORD2:20 pmChicago O'Hare Intl
8h 20m
1 stop
YWG10:40 pmWinnipeg
$268
Find similar
WestJet
Nov 28
YWG6:15 amWinnipeg
7h 20m
1 stop
ORD1:35 pmChicago O'Hare Intl
Dec 5
ORD2:20 pmChicago O'Hare Intl
8h 21m
1 stop
YWG10:41 pmWinnipeg
$301
Find similar

Air Canada flights from Winnipeg to Illinois

Our best Air Canada deals on Winnipeg to Illinois flight tickets
Air Canada
Apr 14
YWG7:15 amWinnipeg
8h 06m
2 stops
STL3:21 pmLambert-St Louis
Apr 15
STL1:30 pmLambert-St Louis
7h 18m
1 stop
YWG8:48 pmWinnipeg
$407
Find similar
Air Canada
Apr 14
YWG6:00 amWinnipeg
9h 21m
2 stops
STL3:21 pmLambert-St Louis
Apr 15
STL1:30 pmLambert-St Louis
7h 18m
1 stop
YWG8:48 pmWinnipeg
$463
Find similar
Air Canada
Apr 14
YWG7:15 amWinnipeg
8h 06m
2 stops
STL3:21 pmLambert-St Louis
Apr 15
STL8:00 amLambert-St Louis
11h 28m
2 stops
YWG7:28 pmWinnipeg
$550
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 November 3, 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 - MDW

YWGMDW

Winnipeg

Thu 12/4

9:00 pm-7:42 pm

2 stops22h 42m

Chicago Midway

Sun 12/7

6:15 am-3:07 pm

1 stop8h 52m

$209

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 12/4

9:00 pm-7:42 pm

2 stops22h 42m

Chicago Midway

Sun 12/7

6:15 am-3:07 pm

1 stop8h 52m

$216

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 12/4

9:00 pm-10:12 pm

2 stops25h 12m

Chicago Midway

Sun 12/7

6:15 am-3:07 pm

1 stop8h 52m

$217

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 1/16

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 1/19

2:20 pm-10:41 pm

1 stop8h 21m

$238

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 2/12

9:00 pm-1:35 pm

1 stop16h 35m

Chicago O'Hare Intl

Mon 2/16

2:20 pm-10:40 pm

1 stop8h 20m

$268

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Tue 4/14

8:30 am-4:26 pm

1 stop7h 56m

Lambert-St Louis

Wed 4/15

1:30 pm-8:48 pm

1 stop7h 18m

$348

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Tue 4/14

7:15 am-3:21 pm

2 stops8h 06m

Lambert-St Louis

Wed 4/15

1:30 pm-8:48 pm

1 stop7h 18m

$407

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Tue 4/14

6:00 am-3:21 pm

2 stops9h 21m

Lambert-St Louis

Wed 4/15

1:30 pm-8:48 pm

1 stop7h 18m

$463

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

11:53 am-6:37 pm

1 stop6h 44m

Chicago Midway

Sun 3/8

6:00 am-3:09 pm

1 stop9h 09m

$548

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 12/4

12:35 pm-11:47 pm

2 stops11h 12m

Chicago Midway

Sun 12/7

9:34 am-7:12 pm

2 stops9h 38m

$603

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 $373.

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 $547. Flights from Winnipeg to Illinois on a Sunday will generally be more expensive and average around $814. 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 $621.

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

$225

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Illinois

1 airport
The best one-way flight to Illinois from Winnipeg in the past 72 hours is $225. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is $454.
The fastest flight from Winnipeg to Illinois takes 2h 21m
Direct flights go from Winnipeg 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 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
8,997 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
Wed 12/3
Wed 12/10
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 $49
Flights to Miamifrom $49
Flights to Chicagofrom $54
Flights to Orlandofrom $47
Flights to Las Vegasfrom $49
Flights to San Franciscofrom $54
Flights to Washington, D.C.from $54
Flights to Bostonfrom $40
Flights to Atlantafrom $40
Flights to Dallasfrom $49
Flights to Seattlefrom $68