HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to Illinois with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$223
(Trip.com)

One-way from

$152
(Kiwi.com)

Popular in

August

Cheapest in

June

Average price

$450

Good round-trip deal

$411 or less

Good one-way deal

$209 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. 6% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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

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 March 28, 2025.

This Trip.com deal was found by Cheapflights users on 3/26. 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.
Mon 6/98:30 amYWG - ORD
1 stop8h 14mWestJet
Tue 6/105:30 pmORD - YWG
1 stop18h 11mWestJet
Deal found 3/26$220
This Trip.com deal was found by Cheapflights users on 3/26. 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.
Tue 6/108:30 amYWG - ORD
1 stop8h 14mMultiple Airlines
Thu 6/125:10 amORD - YWG
1 stop11h 18mMultiple Airlines
Deal found 3/26$296
This United Airlines deal was found by Cheapflights users on 3/26. 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 9/242:15 pmYWG - ORD
Nonstop2h 21mUnited Airlines
Thu 9/254:00 pmORD - YWG
1 stop7h 20mUnited Airlines
Deal found 3/26$368
This Air Canada deal was found by Cheapflights users on 3/25. 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.
Sat 4/262:20 pmYWG - ORD
Nonstop2h 28mAir Canada
Wed 5/712:57 pmORD - YWG
Nonstop2h 34mAir Canada
Deal found 3/25$391
This Delta deal was found by Cheapflights users on 3/27. 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.
Tue 5/278:30 amYWG - MDW
1 stop4h 45mDelta
Wed 5/287:25 pmMDW - YWG
1 stop4h 00mDelta
Deal found 3/27$414
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Thu 4/245:00 amYWG - MDW
1 stop11h 40mMultiple Airlines
Thu 5/18:30 amMDW - YWG
1 stop7h 58mMultiple Airlines
Deal found 3/27$419
This Delta deal was found by Cheapflights users on 3/26. 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.
Sun 4/2012:52 pmYWG - ORD
2 stops7h 58mDelta
Sun 4/276:35 amORD - YWG
1 stop5h 27mDelta
Deal found 3/26$435
This CheapTicketsDeal deal was found by Cheapflights users on 3/27. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/226:40 amYWG - MDW
1 stop10h 39mWestJet
Fri 4/257:00 pmMDW - YWG
1 stop4h 28mWestJet
Deal found 3/27$474
This FlightHub deal was found by Cheapflights users on 3/27. 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 7/3011:45 amYWG - MDW
2 stops21h 00mPorter Airlines
Mon 8/45:20 pmMDW - YWG
2 stops29h 26mPorter Airlines
Deal found 3/27$581

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 March 28, 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

Mon 6/9

8:30 am-4:44 pm

1 stop8h 14m

Chicago O'Hare Intl

Tue 6/10

5:30 pm-11:41 am

1 stop18h 11m

$220

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 6/10

8:30 am-4:44 pm

1 stop8h 14m

Chicago O'Hare Intl

Thu 6/12

5:10 am-4:28 pm

1 stop11h 18m

$296

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 4/26

2:20 pm-4:48 pm

Nonstop2h 28m

Chicago O'Hare Intl

Wed 5/7

12:57 pm-3:31 pm

Nonstop2h 34m

$391

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 5/6

2:20 pm-4:48 pm

Nonstop2h 28m

Chicago O'Hare Intl

Wed 5/7

12:57 pm-3:31 pm

Nonstop2h 34m

$392

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 5/27

8:30 am-1:15 pm

1 stop4h 45m

Chicago Midway

Wed 5/28

7:25 pm-11:25 pm

1 stop4h 00m

$414

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 4/24

5:00 am-4:40 pm

1 stop11h 40m

Chicago Midway

Thu 5/1

8:30 am-4:28 pm

1 stop7h 58m

$419

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 4/20

12:52 pm-8:50 pm

2 stops7h 58m

Chicago O'Hare Intl

Sun 4/27

6:35 am-12:02 pm

1 stop5h 27m

$435

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 4/22

6:40 am-5:19 pm

1 stop10h 39m

Chicago Midway

Fri 4/25

7:00 pm-11:28 pm

1 stop4h 28m

$474

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 7/30

11:45 am-8:45 am

2 stops21h 00m

Chicago Midway

Mon 8/4

5:20 pm-10:46 pm

2 stops29h 26m

$581

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/9

5:30 pm-4:44 pm

1 stop23h 14m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 17 results
1
2

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, August is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $245). Flying from Winnipeg to Illinois in March is currently the most expensive (average of $323). 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 March 28, 2025.

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.

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 March 28, 2025.
Read reviews from past customers who have flown Delta, Porter Airlines and United Airlines from Winnipeg to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,896 reviews
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,603 reviews
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,785 reviews
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Canada
7.0
Good
8,986 reviews
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • What are the cheapest airlines to fly from Winnipeg to Illinois one-way?

    One-way options have recently been found by users for as low as $152 on WestJet. Other airlines that offer cheap prices include Air Canada from $226 and Porter Airlines from $228 one-way.

  • 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 (71%), Air Canada (71%) and United Airlines (71%).

  • What are the cheapest flights from Winnipeg to Illinois?

    Looking for the cheapest flight from Winnipeg to Illinois? While on average our users pay $472, our data indicates the cheapest price to be $150. The most popular route (Winnipeg - Chicago O'Hare Intl), is priced around $261.

  • 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, August is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $245). Flying from Winnipeg to Illinois in March is currently the most expensive (average of $323). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Las Vegas flights
Winnipeg to Newark flights
Winnipeg to Minneapolis flights
Winnipeg to LaGuardia flights
Winnipeg to O'Hare Intl flights
Winnipeg to John F Kennedy Intl flights
Winnipeg to Orlando flights
Winnipeg to Los Angeles flights
Winnipeg to Sky Harbor Intl flights
Winnipeg to Nashville flights
Winnipeg to Atlanta flights
Winnipeg to Denver flights
Winnipeg to Midway flights
Winnipeg to Dulles Intl flights
Winnipeg to Ontario flights
Winnipeg to Baltimore flights
Winnipeg to Fort Lauderdale flights
Winnipeg to Hobby flights
Winnipeg to Honolulu flights
Winnipeg to Reagan-National flights
Winnipeg to San Francisco flights
Winnipeg to Miami flights
Winnipeg to Santa Ana flights
Winnipeg to Seattle flights
Winnipeg to Dallas/Fort Worth flights
Winnipeg to Philadelphia flights
Winnipeg to George Bush Intcntl flights
Winnipeg to Tampa flights
Winnipeg to Boston flights
Winnipeg to Love Field flights
Winnipeg to San Diego flights
Winnipeg to Detroit flights
Winnipeg to Fort Myers flights
Winnipeg to Memphis flights
Winnipeg to Daytona Beach flights
Winnipeg to Bozeman flights
Winnipeg to Palm Springs flights
Winnipeg to Kansas City flights
Winnipeg to New Orleans flights
Winnipeg to Harrisburg flights
Winnipeg to Columbus flights
Winnipeg to Portland flights
Winnipeg to San Jose flights
Winnipeg to Albany flights
Winnipeg to Pensacola flights
Winnipeg to Traverse City flights
Winnipeg to Sacramento flights
Winnipeg to Anchorage flights
Winnipeg to Burbank flights
Winnipeg to Medford flights

Top 2 airlines flying from Winnipeg to Illinois

Discover the top 2 airlines 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$349Average$572FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$443Average$547FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.