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$118+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Winnipeg to Illinois

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Illinois (USIL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$325
(Mytrip)

One-way from

$118
(Trip.com)
From Winnipeg to Illinois
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One-way flight from Winnipeg to Illinois
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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 January 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/136:20 amYWG - ORD
1 stop9h 36mWestJet
Mon 3/174:45 pmORD - YWG
2 stops18h 30mWestJet
Deal found 1/20$325
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/136:00 amYWG - ORD
2 stops9h 56mMultiple Airlines
Mon 3/177:42 pmORD - YWG
3 stops29h 02mMultiple Airlines
Deal found 1/20$361
This Air Canada deal was found by Cheapflights users on 1/20. 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 2/107:30 amYWG - ORD
1 stop5h 41mAir Canada
Wed 2/1210:53 amORD - YWG
1 stop6h 25mAir Canada
Deal found 1/20$434
This Delta deal was found by Cheapflights users on 1/20. 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.
Thu 3/138:50 amYWG - MDW
1 stop5h 25mDelta
Mon 3/1710:25 amMDW - YWG
1 stop6h 28mDelta
Deal found 1/20$445
This Delta deal was found by Cheapflights users on 1/20. 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 2/196:40 amYWG - ORD
2 stops11h 45mDelta
Wed 2/266:45 amORD - YWG
2 stops9h 58mDelta
Deal found 1/20$445
This Trip.com deal was found by Cheapflights users on 1/19. 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 3/256:50 amYWG - MDW
1 stop11h 28mWestJet
Sat 3/2911:27 amMDW - YWG
1 stop8h 48mWestJet
Deal found 1/19$488
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/135:15 pmYWG - MDW
2 stops17h 05mMultiple Airlines
Mon 3/1711:15 amMDW - YWG
2 stops12h 17mMultiple Airlines
Deal found 1/20$509
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Thu 3/132:15 pmYWG - ORD
Nonstop2h 22mUnited Airlines
Mon 3/1712:58 pmORD - YWG
Nonstop2h 30mUnited Airlines
Deal found 1/20$534
This Delta deal was found by Cheapflights users on 1/20. 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.
Thu 4/248:50 amYWG - STL
2 stops14h 48mDelta
Sun 4/277:10 pmSTL - YWG
1 stop21h 18mDelta
Deal found 1/20$564
This Porter Airlines deal was found by Cheapflights users on 1/19. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2511:35 amYWG - MDW
2 stops22h 45mPorter Airlines
Sat 3/2912:55 pmMDW - YWG
2 stops29h 09mPorter Airlines
Deal found 1/19$589
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Thu 3/64:30 pmYWG - STL
2 stops25h 23mUnited Airlines
Thu 3/138:00 amSTL - YWG
1 stop7h 28mUnited Airlines
Deal found 1/20$604
This Justfly.com deal was found by Cheapflights users on 1/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/245:00 amYWG - STL
2 stops15h 33mWestJet
Sun 4/275:40 pmSTL - YWG
2 stops25h 44mWestJet
Deal found 1/20$636

Find flights from Winnipeg to Illinois within your budget

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 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 3/13

6:20 am-3:56 pm

1 stop9h 36m

Chicago O'Hare Intl

Mon 3/17

4:45 pm-11:15 am

2 stops18h 30m

$325

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 3/13

6:00 am-3:56 pm

2 stops9h 56m

Chicago O'Hare Intl

Mon 3/17

7:42 pm-12:44 am

3 stops29h 02m

$361

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 2/10

7:30 am-1:11 pm

1 stop5h 41m

Chicago O'Hare Intl

Wed 2/12

10:53 am-5:18 pm

1 stop6h 25m

$434

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 3/13

6:50 am-12:36 pm

2 stops5h 46m

Chicago Midway

Mon 3/17

10:25 am-4:53 pm

1 stop6h 28m

$445

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 2/19

12:45 pm-8:53 pm

2 stops8h 08m

Chicago O'Hare Intl

Wed 2/26

10:10 am-4:43 pm

1 stop6h 33m

$445

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/25

6:50 am-6:18 pm

1 stop11h 28m

Chicago Midway

Sat 3/29

11:27 am-8:15 pm

1 stop8h 48m

$488

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 3/13

5:15 pm-10:20 am

2 stops17h 05m

Chicago Midway

Mon 3/17

11:15 am-11:32 pm

2 stops12h 17m

$509

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 3/13

2:15 pm-4:37 pm

Nonstop2h 22m

Chicago O'Hare Intl

Mon 3/17

12:58 pm-3:28 pm

Nonstop2h 30m

$534

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Thu 4/24

8:50 am-11:38 pm

2 stops14h 48m

Lambert-St Louis

Sun 4/27

7:10 pm-4:28 pm

1 stop21h 18m

$564

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/25

11:35 am-10:20 am

2 stops22h 45m

Chicago Midway

Sat 3/29

12:55 pm-6:04 pm

2 stops29h 09m

$589

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 23 results
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2
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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.

Travel insights for flights from Winnipeg to Illinois

Get recent, data-driven insights about flights from Winnipeg to Illinois including ideal travel times, pricing trends, and more.

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 $320). 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 21, 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.

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 21, 2025.

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

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 January 21, 2025.
Read reviews from past customers who have flown WestJet, Air Canada 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
8,521 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.6

Reviews

1 / 10

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

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.6

Reviews

1 / 10

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

Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.6

Reviews

1 / 10

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

United Airlines
7.4
Good
8,984 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.6

Reviews

1 / 10

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

WestJet
7.2
Good
2,828 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.6

Reviews

1 / 10

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

Air Canada
7.0
Good
8,633 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.6

Reviews

1 / 10

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 $157 on WestJet. Other airlines that offer cheap prices include Delta from $212 and Air Canada from $240 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 $567, our data indicates the cheapest price to be $152. The most popular route (Winnipeg - Chicago O'Hare Intl), is priced around $271.

  • 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 $320). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$271Average$556FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$441Average$533FlexibilityNo cancel feeOn-time69%
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