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$134+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
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 December 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/314:55 pmYWG - ORD
2 stops17h 23mMultiple Airlines
Mon 1/51:32 pmORD - YWG
1 stop11h 11mMultiple Airlines
Deal found 12/14$580
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Tue 12/238:00 amYWG - ORD
1 stop26h 18mMultiple Airlines
Tue 1/612:09 pmORD - YWG
2 stops23h 26mMultiple Airlines
Deal found 12/14$603
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Tue 12/308:00 amYWG - ORD
1 stop30h 21mMultiple Airlines
Mon 1/51:32 pmORD - YWG
1 stop11h 11mMultiple Airlines
Deal found 12/14$606
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/292:20 pmYWG - ORD
Nonstop2h 43mUnited Airlines
Thu 1/18:45 amORD - YWG
1 stop12h 06mUnited Airlines
Deal found 12/14$631
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:40 amYWG - ORD
1 stop15h 19mUnited Airlines
Thu 1/110:56 amORD - YWG
1 stop9h 55mUnited Airlines
Deal found 12/14$636
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/208:00 amYWG - ORD
1 stop30h 53mMultiple Airlines
Tue 1/65:29 pmORD - YWG
2 stops42h 06mMultiple Airlines
Deal found 12/14$669
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Mon 12/294:55 pmYWG - ORD
2 stops21h 22mMultiple Airlines
Mon 1/51:32 pmORD - YWG
1 stop11h 11mMultiple Airlines
Deal found 12/14$687
This Air Canada deal was found by Cheapflights users on 12/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/292:20 pmYWG - ORD
Nonstop2h 43mAir Canada
Fri 1/29:10 amORD - YWG
Nonstop2h 47mAir Canada
Deal found 12/14$688
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/317:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
Mon 1/56:14 pmMDW - YWG
2 stops30h 28mMultiple Airlines
Deal found 12/14$691
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/317:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
Sun 1/46:08 pmMDW - YWG
2 stops25h 04mMultiple Airlines
Deal found 12/14$727
This FlightHub deal was found by Cheapflights users on 12/14. 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.
Tue 12/236:45 amYWG - MDW
2 stops10h 34mWestJet
Tue 1/61:49 pmMDW - YWG
1 stop21h 14mWestJet
Deal found 12/14$738
This FlightHub deal was found by Cheapflights users on 12/15. 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.
Thu 12/256:45 amYWG - MDW
2 stops10h 34mWestJet
Sun 12/2811:48 amMDW - YWG
1 stop5h 07mWestJet
Deal found 12/15$768

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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$235
(Kiwi.com)

One-way from

$134
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$602

Good round-trip deal

$384 or less

Good one-way deal

$362 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 ($48 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 December 2025
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 December 15, 2025.
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

Fri 1/30

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 3/2

2:20 pm-12:40 am

1 stop10h 20m

$243

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 2/19

6:55 pm-1:35 pm

1 stop18h 40m

Chicago O'Hare Intl

Mon 2/23

2:20 pm-10:40 pm

1 stop8h 20m

$256

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 1/12

9:00 pm-10:34 am

2 stops13h 34m

Chicago Midway

Mon 1/19

12:57 pm-12:43 am

1 stop11h 46m

$263

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 2/1

7:30 am-10:19 pm

1 stop14h 49m

Chicago Midway

Thu 2/5

5:01 pm-3:09 pm

1 stop22h 08m

$267

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 2/19

9:00 pm-1:35 pm

1 stop16h 35m

Chicago O'Hare Intl

Mon 2/23

4:42 pm-6:05 pm

2 stops25h 23m

$275

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 1/17

5:00 am-9:03 pm

2 stops16h 03m

Chicago O'Hare Intl

Tue 1/20

7:20 am-12:35 am

2 stops17h 15m

$291

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 1/10

9:00 pm-6:58 pm

2 stops45h 58m

Chicago O'Hare Intl

Sat 1/17

6:02 pm-12:43 am

1 stop30h 41m

$292

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 2/1

8:20 pm-9:03 pm

2 stops24h 43m

Chicago O'Hare Intl

Thu 2/5

8:43 pm-7:09 pm

2 stops22h 26m

$330

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 1/30

2:40 pm-6:16 pm

3 stops27h 36m

Chicago O'Hare Intl

Mon 3/2

2:20 pm-6:05 pm

1 stop27h 45m

$348

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Sat 3/14

12:53 pm-5:05 pm

1 stop4h 12m

Lambert-St Louis

Sat 3/21

6:10 am-12:03 pm

1 stop5h 53m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 42 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 $466). 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 December 15, 2025.

It’s typically best to fly out from Winnipeg to Illinois in the afternoon. Doing so could potentially save you 36% on the flight price compared to flying in the morning, which is usually more expensive.

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 December 15, 2025.
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
9,092 reviews

Entertainment

7.1

Food

6.6

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,092 reviews
United Airlines
7.4
Good
9,092 reviews

Entertainment

7.1

Food

6.6

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 4h 12m. Fly via WestJet, Delta, or Air Canada 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 Avianca (82%), SkyWest Airlines (80%) and Air Canada (80%).

  • What are the cheapest flights from Winnipeg to Illinois?

    Looking for the cheapest flight from Winnipeg to Illinois? While on average our users pay $503, our data indicates the cheapest price to be $148. The most popular route (Winnipeg - Chicago O'Hare Intl), is priced around $252.

  • 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 $466). 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.

See more FAQs

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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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$471FlexibilityNo cancel feeOn-time69%

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