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$130+ 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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
1 adult, Economy
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Find 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 octubre 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
vie. 12/57:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
lun. 12/88:42 pmMDW - YWG
2 stops21h 24mMultiple Airlines
Deal found 10/28$196
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
vie. 12/57:30 amYWG - ORD
1 stop28h 24mMultiple Airlines
dom. 12/710:24 amORD - YWG
2 stops14h 17mMultiple Airlines
Deal found 10/29$198
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
mié. 11/267:30 amYWG - ORD
1 stop16h 38mMultiple Airlines
mié. 12/38:00 amORD - YWG
2 stops16h 41mMultiple Airlines
Deal found 10/29$213
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
jue. 12/49:00 pmYWG - MDW
2 stops25h 12mMultiple Airlines
dom. 12/76:15 amMDW - YWG
1 stop8h 52mMultiple Airlines
Deal found 10/29$214
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
mar. 11/119:00 pmYWG - MDW
2 stops15h 41mMultiple Airlines
mar. 11/181:56 pmMDW - YWG
1 stop25h 11mMultiple Airlines
Deal found 10/29$215
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
mar. 11/119:00 pmYWG - ORD
2 stops14h 14mMultiple Airlines
mar. 11/1812:37 pmORD - YWG
1 stop26h 30mMultiple Airlines
Deal found 10/29$215
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
mié. 12/107:30 amYWG - ORD
1 stop11h 16mMultiple Airlines
mié. 12/174:01 pmORD - YWG
2 stops32h 38mMultiple Airlines
Deal found 10/27$218
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
lun. 12/19:00 pmYWG - ORD
2 stops18h 12mMultiple Airlines
vie. 12/56:11 amORD - YWG
1 stop8h 56mMultiple Airlines
Deal found 10/27$237
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
vie. 12/57:30 amYWG - ORD
1 stop28h 24mMultiple Airlines
lun. 12/89:27 pmORD - YWG
2 stops27h 12mMultiple Airlines
Deal found 10/28$251
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
sáb. 11/159:00 pmYWG - ORD
2 stops27h 11mMultiple Airlines
sáb. 12/131:24 pmORD - YWG
1 stop25h 43mMultiple Airlines
Deal found 10/28$266
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
vie. 11/287:30 amYWG - MDW
1 stop7h 10mMultiple Airlines
vie. 12/58:42 pmMDW - YWG
2 stops27h 59mMultiple Airlines
Deal found 10/29$274
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
vie. 11/217:30 amYWG - MDW
1 stop7h 10mMultiple Airlines
mar. 11/256:05 amMDW - YWG
2 stops18h 36mMultiple Airlines
Deal found 10/29$285

Cheap flight deals from Winnipeg to Illinois

Keep the following information in mind while searching for Winnipeg to Illinois flight deals. Data was last updated octubre 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$196
(Kiwi.com)

One-way from

$130
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$373

Good round-trip deal

$454 or less

Good one-way deal

$225 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. 5% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 octubre 29, 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 - MDW

YWGMDW

Winnipeg

vie. 12/5

7:30 am-10:12 pm

1 stop14h 42m

Chicago Midway

lun. 12/8

8:42 pm-6:06 pm

2 stops21h 24m

$198

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

vie. 12/5

7:30 am-11:54 am

1 stop28h 24m

Chicago O'Hare Intl

dom. 12/7

6:11 am-3:07 pm

1 stop8h 56m

$202

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

mié. 11/26

7:30 am-12:08 am

1 stop16h 38m

Chicago O'Hare Intl

mié. 12/3

8:00 am-12:41 am

2 stops16h 41m

$213

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

jue. 12/4

9:00 pm-10:12 pm

2 stops25h 12m

Chicago Midway

dom. 12/7

6:15 am-3:07 pm

1 stop8h 52m

$214

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

mar. 11/11

9:00 pm-12:41 pm

2 stops15h 41m

Chicago Midway

mar. 11/18

1:56 pm-3:07 pm

1 stop25h 11m

$215

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

lun. 12/1

9:00 pm-3:12 pm

2 stops18h 12m

Chicago O'Hare Intl

vie. 12/5

6:11 am-3:07 pm

1 stop8h 56m

$237

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

mié. 1/7

7:30 am-10:15 pm

1 stop14h 45m

Chicago Midway

mié. 1/14

7:10 am-3:07 pm

1 stop7h 57m

$251

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

vie. 12/5

7:30 am-11:54 am

1 stop28h 24m

Chicago O'Hare Intl

lun. 12/8

9:27 pm-12:39 am

2 stops27h 12m

$253

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

vie. 11/28

7:30 am-2:40 pm

1 stop7h 10m

Chicago Midway

vie. 12/5

6:15 am-3:07 pm

1 stop8h 52m

$278

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

vie. 11/21

7:30 am-2:40 pm

1 stop7h 10m

Chicago Midway

mar. 11/25

6:05 am-12:41 am

2 stops18h 36m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 45 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 March is currently the most expensive (average of $397). 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 octubre 29, 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.

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 octubre 29, 2025.
Get a feel of what it's like to fly with United Airlines and Air Canada 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
8,999 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Food

6.6

Entertainment

7.1

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
8,999 reviews
United Airlines
7.4
Good
8,999 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Food

6.6

Entertainment

7.1

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.
Air Canada
7.1
Good
10,372 reviews
United Airlines
7.4
Good
8,999 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Food

6.6

Entertainment

7.1

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 7h 56m. Fly via United Airlines, 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 SkyWest Airlines (85%), Air Canada (85%) and United Airlines (85%).

  • What are the cheapest flights from Winnipeg to Illinois?

    Looking for the cheapest flight from Winnipeg to Illinois? While on average our users pay $432, our data indicates the cheapest price to be $207. The most popular route (Winnipeg - Chicago O'Hare Intl), is priced around $224.

  • 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 March is currently the most expensive (average of $397). 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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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 octubre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$471FlexibilityNo cancel feeOn-time69%

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