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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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
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 December 18, 2024.

Round-trip from

$286
(Kiwi.com)

One-way from

$130
(Kiwi.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 December 18, 2024.

This Mytrip deal was found by Cheapflights users on 12/16. 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.
Mon 12/3011:35 amYWG - ORD
2 stops20h 12mMultiple Airlines
Sun 2/211:10 amORD - YWG
2 stops27h 58mMultiple Airlines
Deal found 12/16$499
This Mytrip deal was found by Cheapflights users on 12/16. 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.
Mon 12/305:00 amYWG - MDW
1 stop11h 40mPorter Airlines
Sun 2/21:05 pmMDW - YWG
1 stop10h 35mPorter Airlines
Deal found 12/16$517
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/305:55 pmYWG - ORD
1 stop15h 02mUnited Airlines
Sun 2/27:10 amORD - YWG
1 stop6h 17mUnited Airlines
Deal found 12/16$543
This Mytrip deal was found by Cheapflights users on 12/16. 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.
Mon 12/307:00 pmYWG - MDW
1 stop15h 20mMultiple Airlines
Sun 2/21:26 pmMDW - YWG
2 stops21h 19mMultiple Airlines
Deal found 12/16$563
This WestJet deal was found by Cheapflights users on 12/16. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/308:00 pmYWG - MDW
2 stops21h 11mWestJet
Sun 2/21:26 pmMDW - YWG
2 stops21h 56mWestJet
Deal found 12/16$659
This Air Canada deal was found by Cheapflights users on 12/16. 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 12/302:15 pmYWG - ORD
Nonstop2h 36mAir Canada
Sun 2/27:20 amORD - YWG
1 stop9h 08mAir Canada
Deal found 12/16$671
This Justfly.com deal was found by Cheapflights users on 12/17. 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.
Mon 12/308:00 pmYWG - ORD
2 stops37h 21mWestJet
Fri 1/35:30 pmORD - YWG
2 stops31h 05mWestJet
Deal found 12/17$809

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 1/19

7:30 am-9:32 pm

1 stop14h 02m

Chicago Midway

Fri 1/24

6:40 am-3:10 pm

1 stop8h 30m

$286

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 1/15

7:30 am-5:55 am

2 stops22h 25m

Chicago O'Hare Intl

Wed 1/22

3:56 pm-12:39 am

3 stops32h 43m

$331

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 1/19

7:30 am-2:51 pm

1 stop7h 21m

Chicago O'Hare Intl

Fri 1/24

10:53 am-5:18 pm

1 stop6h 25m

$369

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 1/15

5:37 pm-9:58 pm

1 stop4h 21m

Chicago O'Hare Intl

Wed 1/22

11:05 am-11:42 pm

2 stops12h 37m

$400

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 1/19

12:45 pm-5:47 pm

1 stop5h 02m

Chicago Midway

Fri 1/24

9:34 am-4:47 pm

2 stops7h 13m

$434

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 4/4

12:15 pm-6:30 pm

1 stop6h 15m

Chicago O'Hare Intl

Mon 4/7

5:00 am-1:09 pm

1 stop8h 09m

$436

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 1/17

5:37 pm-3:30 pm

1 stop21h 53m

Chicago O'Hare Intl

Sun 1/19

4:58 pm-7:10 pm

2 stops26h 12m

$446

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 1/16

5:00 am-6:14 pm

2 stops13h 14m

Chicago Midway

Thu 1/23

10:19 am-4:47 pm

1 stop6h 28m

$470

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 12/30

5:00 am-4:40 pm

1 stop11h 40m

Chicago Midway

Sun 2/2

1:05 pm-11:40 pm

1 stop10h 35m

$517

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Fri 1/17

5:37 pm-2:54 pm

1 stop21h 17m

Lambert-St Louis

Mon 1/20

10:22 am-7:37 pm

2 stops33h 15m

$575

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 18 results
1
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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, September is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $232). Flying from Winnipeg to Illinois in June is currently the most expensive (average of $308). 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 18, 2024.

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 December 18, 2024.
Read reviews from past customers who have flown United Airlines, Air Canada and Delta 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
8,604 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.6

Comfort

7.9

Food

7.3

Overall

8.0

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
8,604 reviews
Delta
8.0
Very good
8,604 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.6

Comfort

7.9

Food

7.3

Overall

8.0

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
283 reviews
Delta
8.0
Very good
8,604 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.6

Comfort

7.9

Food

7.3

Overall

8.0

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
9,055 reviews
Delta
8.0
Very good
8,604 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.6

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 10

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

WestJet
7.3
Good
2,818 reviews
Delta
8.0
Very good
8,604 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.6

Comfort

7.9

Food

7.3

Overall

8.0

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
8,382 reviews
Delta
8.0
Very good
8,604 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.6

Comfort

7.9

Food

7.3

Overall

8.0

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 $209 on Air Canada. Other airlines that offer cheap prices include United Airlines from $227 and Delta from $298 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 (84%), United Airlines (84%) 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 $579, our data indicates the cheapest price to be $219. The most popular route (Winnipeg - Chicago O'Hare Intl), is priced around $299.

  • 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, September is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $232). Flying from Winnipeg to Illinois in June is currently the most expensive (average of $308). 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 3 airlines flying from Winnipeg to Illinois

Discover the top 3 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$289Average$550FlexibilityNo cancel feeOn-time67%
DeltaCheapest$370Average$671FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$441Average$533FlexibilityNo cancel feeOn-time69%
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