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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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 November 21, 2024.

This Mytrip deal was found by Cheapflights users on 11/20. 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.
Fri 12/67:30 amYWG - ORD
2 stops17h 03mMultiple Airlines
Thu 12/126:33 pmORD - YWG
2 stops20h 37mMultiple Airlines
Deal found 11/20$358
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/67:30 amYWG - MDW
1 stop9h 42mMultiple Airlines
Thu 12/1211:25 amMDW - YWG
2 stops9h 44mMultiple Airlines
Deal found 11/20$402
This Air Canada deal was found by Cheapflights users on 11/20. 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.
Sat 12/147:30 amYWG - ORD
1 stop7h 21mAir Canada
Wed 12/187:19 amORD - YWG
1 stop6h 39mAir Canada
Deal found 11/20$404
This United Airlines deal was found by Cheapflights users on 11/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/182:15 pmYWG - ORD
Nonstop2h 30mUnited Airlines
Wed 12/2512:56 pmORD - YWG
Nonstop2h 32mUnited Airlines
Deal found 11/19$430
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/186:55 amYWG - MDW
1 stop6h 36mDelta
Wed 12/254:50 pmMDW - YWG
1 stop6h 53mDelta
Deal found 11/19$470
This Delta deal was found by Cheapflights users on 11/20. 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.
Fri 12/1312:35 pmYWG - ORD
1 stop7h 15mDelta
Tue 12/171:45 pmORD - YWG
2 stops9h 49mDelta
Deal found 11/20$472
This KAYAK deal was found by Cheapflights users on 11/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/145:00 amYWG - ORD
2 stops14h 29mWestJet
Tue 12/176:20 amORD - YWG
1 stop5h 25mWestJet
Deal found 11/20$522
This Orbitz deal was found by Cheapflights users on 11/20. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/145:00 amYWG - MDW
2 stops17h 06mWestJet
Tue 12/1712:44 pmMDW - YWG
2 stops11h 51mWestJet
Deal found 11/20$536
This Porter Airlines deal was found by Cheapflights users on 11/20. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1311:35 amYWG - MDW
2 stops24h 25mPorter Airlines
Tue 12/1711:15 amMDW - YWG
2 stops30h 49mPorter Airlines
Deal found 11/20$541
This Aeromexico deal was found by Cheapflights users on 11/20. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/68:00 pmYWG - ORD
2 stops27h 14mAeromexico
Sun 12/81:00 amORD - YWG
2 stops34h 25mAeromexico
Deal found 11/20$2,169

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 1/7

7:30 am-4:14 pm

1 stop8h 44m

Chicago Midway

Mon 1/13

6:15 am-3:10 pm

1 stop8h 55m

$261

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/6

7:30 am-12:33 am

2 stops17h 03m

Chicago O'Hare Intl

Thu 12/12

6:33 pm-3:10 pm

2 stops20h 37m

$358

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 3/13

8:15 am-3:56 pm

1 stop7h 41m

Chicago O'Hare Intl

Mon 3/17

4:45 pm-12:44 am

1 stop7h 59m

$390

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 12/14

7:30 am-2:51 pm

1 stop7h 21m

Chicago O'Hare Intl

Wed 12/18

7:19 am-1:58 pm

1 stop6h 39m

$404

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 1/14

2:15 pm-4:51 pm

Nonstop2h 36m

Chicago O'Hare Intl

Sun 2/16

9:50 am-5:18 pm

1 stop7h 28m

$427

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 1/10

6:55 am-6:14 pm

2 stops11h 19m

Chicago Midway

Sun 1/12

9:34 am-4:47 pm

2 stops7h 13m

$428

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 1/7

5:37 pm-9:58 pm

1 stop4h 21m

Chicago O'Hare Intl

Sun 1/12

6:55 am-4:47 pm

2 stops9h 52m

$428

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 1/7

5:37 pm-12:46 pm

1 stop19h 09m

Chicago Midway

Wed 1/15

10:19 am-4:47 pm

1 stop6h 28m

$484

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 12/13

11:35 am-12:00 pm

2 stops24h 25m

Chicago Midway

Tue 12/17

11:15 am-6:04 pm

2 stops30h 49m

$541

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Wed 1/22

7:30 am-11:37 pm

1 stop16h 07m

Lambert-St Louis

Sun 1/26

7:07 pm-3:10 pm

1 stop20h 03m

$548

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 24 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.

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 November 21, 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.

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 November 21, 2024.

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 November 21, 2024.
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
8,759 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

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
8,759 reviews
Delta
8.0
Very good
8,759 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Reviews

1 / 10

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

Porter Airlines
7.8
Good
286 reviews
Delta
8.0
Very good
8,759 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

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
9,173 reviews
Delta
8.0
Very good
8,759 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

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
2,810 reviews
Delta
8.0
Very good
8,759 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

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
8,238 reviews
Delta
8.0
Very good
8,759 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

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 $223 on Porter Airlines. Other airlines that offer cheap prices include Air Canada from $228 and United Airlines from $239 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 (87%), United Airlines (87%) and Air Canada (87%).

  • What are the cheapest flights from Winnipeg to Illinois?

    Looking for the cheapest flight from Winnipeg to Illinois? While on average our users pay $621, our data indicates the cheapest price to be $209. The most popular route (Winnipeg - Chicago O'Hare Intl), is priced around $227.

  • 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 2,629,791 searches. Data last updated November 21, 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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