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$148+ Cheap flights from Winnipeg (YWG) to Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Winnipeg to Illinois

Cheapest flights from Winnipeg to Illinois
Explore the most affordable flight options available from Winnipeg to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This FlightHub deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:55 pm
YWG
-
ORD
1 stop21h 45m
WestJet
Thu 4/305:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 1/27$257
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:00 am
YWG
-
ORD
2 stops9h 40m
WestJet
Tue 6/95:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 1/27$260
This Trip.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:15 am
YWG
-
ORD
1 stop7h 20m
WestJet
Mon 3/92:20 pm
ORD
-
YWG
1 stop8h 20m
WestJet
Deal found 1/27$262
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:30 am
YWG
-
ORD
1 stop27h 46m
Multiple Airlines
Tue 3/107:41 pm
ORD
-
YWG
2 stops28h 59m
Multiple Airlines
Deal found 1/28$289
This Trip.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:00 pm
YWG
-
ORD
1 stop16h 35m
WestJet
Mon 3/92:20 pm
ORD
-
YWG
1 stop8h 20m
WestJet
Deal found 1/27$294
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:30 am
YWG
-
ORD
1 stop9h 22m
Multiple Airlines
Wed 3/46:02 pm
ORD
-
YWG
2 stops30h 38m
Multiple Airlines
Deal found 1/28$309
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/139:05 pm
YWG
-
ORD
1 stop19h 35m
WestJet
Tue 6/165:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 1/27$318
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:30 am
YWG
-
MDW
1 stop12h 17m
Multiple Airlines
Tue 3/106:00 am
MDW
-
YWG
2 stops18h 40m
Multiple Airlines
Deal found 1/28$320
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:30 am
YWG
-
MDW
1 stop11h 37m
Multiple Airlines
Wed 3/47:15 am
MDW
-
YWG
2 stops17h 25m
Multiple Airlines
Deal found 1/28$348
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:55 am
YWG
-
STL
1 stop5h 10m
Delta
Tue 3/176:29 am
STL
-
YWG
1 stop4h 32m
Delta
Deal found 1/27$351
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:30 am
YWG
-
MDW
1 stop12h 17m
Multiple Airlines
Mon 3/99:51 pm
MDW
-
YWG
2 stops37h 41m
Multiple Airlines
Deal found 1/27$359
This FlightHub deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:45 am
YWG
-
STL
2 stops10h 20m
WestJet
Tue 3/176:29 am
STL
-
YWG
1 stop4h 32m
WestJet
Deal found 1/27$380

Find flight deals from Winnipeg to Illinois

Keep the following information in mind while searching for Winnipeg to Illinois flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$257
(FlightHub)

One-way from

$148
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$477

Good round-trip deal

$338 or less

Good one-way deal

$243 or less
Provider with most accurate pricing for Winnipeg-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Chicago (CHI) flights.
Search Deals
From Winnipeg to Illinois
Search Deals
One-way flight from Winnipeg to Illinois
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Winnipeg to Illinois.
Search Deals
Price to beat on a one-way flight from Winnipeg to Illinois.
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Winnipeg to Illinois that are best for you.

Fly from

Winnipeg

Fly to

Illinois

Route

Depart

Return

Price

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

$257

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 6/5

7:00 am-4:40 pm

2 stops9h 40m

Chicago O'Hare Intl

Tue 6/9

5:30 pm-12:55 am

1 stop7h 25m

$260

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/6

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 3/9

2:20 pm-10:40 pm

1 stop8h 20m

$262

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/6

7:30 am-11:16 am

1 stop27h 46m

Chicago O'Hare Intl

Tue 3/10

7:41 pm-3:09 pm

1 stop19h 28m

$291

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 6/13

9:05 pm-4:40 pm

1 stop19h 35m

Chicago O'Hare Intl

Tue 6/16

5:30 pm-12:55 am

1 stop7h 25m

$318

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 2/25

7:30 am-7:07 pm

1 stop11h 37m

Chicago Midway

Wed 3/4

7:15 am-12:40 am

2 stops17h 25m

$348

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/13

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 3/30

2:20 pm-12:07 pm

2 stops21h 47m

$350

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

$351

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Wed 3/11

6:45 am-5:05 pm

2 stops10h 20m

Lambert-St Louis

Tue 3/17

6:29 am-11:01 am

1 stop4h 32m

$380

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Sun 3/1

5:19 pm-11:23 pm

1 stop6h 04m

Lambert-St Louis

Wed 3/4

6:10 am-11:01 am

1 stop4h 51m

$398

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 43 results
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Best time to book a flight from Winnipeg to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Illinois

What is the cheapest month to book a flight from Winnipeg to Illinois?

Currently, May is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $145). Flying from Winnipeg to Illinois in January is currently the most expensive (average of $515). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YWG to IL?

Find hourly flight availability from Winnipeg to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Illinois as you normally would.

Weekly flight availability from Winnipeg to Illinois

Explore weekly flight availability from Winnipeg to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 29, 2026.

The most flights from YWG to USIL are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Winnipeg to Illinois?

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated January 29, 2026.
Get a feel of what it's like to fly with United Airlines from Winnipeg to Illinois by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,215 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Illinois?

    Winnipeg (YWG), located 4.6 mi from the city center, is the airport you fly out of when you book flights from Winnipeg to Illinois.

  • How long is the flight from Winnipeg to Illinois?

    There are many flights that can get you from Winnipeg to Illinois in 5h 10m. Fly via WestJet or Delta to get the fastest option. Winnipeg and Illinois are separated by a distance of 841 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Winnipeg to Illinois?

    While some choose either Winnipeg - Chicago Midway or Winnipeg - Lambert-St Louis, Winnipeg - Chicago O'Hare Intl is the most popular route from Winnipeg to Illinois.

  • What are the most reliable airlines from Winnipeg to Illinois?

    The top 3 most reliable airlines when flying from Winnipeg to Illinois are SkyWest Airlines (77%), Air Canada (77%) and Avianca (77%).

  • What are the cheapest flights from Winnipeg to Illinois?

    Looking for the cheapest flight from Winnipeg to Illinois? While on average our users pay $661, our data indicates the cheapest price to be $197. The most popular route (Winnipeg - Chicago O'Hare Intl), is priced around $308.

  • Can I find deals for flights from Winnipeg to Illinois that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Illinois.

  • Can I find deals for business class flights from Winnipeg to Illinois?

    Yes. Cheapflights offers flight deals from Winnipeg to Illinois by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Illinois?

    Currently, May is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $145). Flying from Winnipeg to Illinois in January is currently the most expensive (average of $515). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Winnipeg to Illinois

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Top airline flying from Winnipeg to Illinois

Discover the top airline that operate flights from Winnipeg to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$469FlexibilityNo cancel feeOn-time69%

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