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$138+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$247
(Mytrip)

One-way from

$138
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$433

Good round-trip deal

$281 or less

Good one-way deal

$293 or less
Provider with most accurate pricing for Winnipeg-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Winnipeg-Chicago (CHI) flights.
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From Winnipeg to Illinois
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One-way flight from Winnipeg to Illinois
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Winnipeg to Illinois.
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Price to beat on a 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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/217:30 amYWG - ORD
1 stop25h 14mMultiple Airlines
Mon 3/248:33 pmORD - YWG
1 stop18h 35mMultiple Airlines
Deal found 2/19$247
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Thu 3/68:15 amYWG - ORD
1 stop7h 41mWestJet
Mon 3/104:45 pmORD - YWG
1 stop7h 59mWestJet
Deal found 2/20$248
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 3/215:00 amYWG - MDW
1 stop11h 40mMultiple Airlines
Mon 3/246:20 amMDW - YWG
1 stop8h 48mMultiple Airlines
Deal found 2/20$350
This Air Canada deal was found by Cheapflights users on 2/20. 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 4/262:20 pmYWG - ORD
Nonstop2h 28mAir Canada
Wed 4/3012:57 pmORD - YWG
Nonstop2h 34mAir Canada
Deal found 2/20$380
This United Airlines deal was found by Cheapflights users on 2/20. 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 4/102:20 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Mon 4/147:10 amORD - YWG
1 stop5h 59mUnited Airlines
Deal found 2/20$445
This Delta deal was found by Cheapflights users on 2/20. 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 10/316:40 amYWG - MDW
1 stop6h 22mDelta
Mon 11/36:45 pmMDW - YWG
1 stop4h 37mDelta
Deal found 2/20$452
This CheapTicketsDeal deal was found by Cheapflights users on 2/19. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/285:00 amYWG - MDW
2 stops13h 11mWestJet
Mon 3/31:26 pmMDW - YWG
1 stop10h 12mWestJet
Deal found 2/19$472
This Mytrip deal was found by Cheapflights users on 2/18. 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.
Tue 5/136:55 pmYWG - MDW
1 stop21h 29mPorter Airlines
Sat 5/179:15 amMDW - YWG
1 stop25h 35mPorter Airlines
Deal found 2/18$490
This Delta deal was found by Cheapflights users on 2/20. 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 10/316:40 amYWG - ORD
2 stops9h 54mDelta
Tue 11/41:35 pmORD - YWG
2 stops9h 47mDelta
Deal found 2/20$497
This Delta deal was found by Cheapflights users on 2/19. 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.
Sun 4/68:50 amYWG - STL
2 stops14h 40mDelta
Sat 5/35:33 pmSTL - YWG
1 stop5h 55mDelta
Deal found 2/19$562
This Air Canada deal was found by Cheapflights users on 2/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/136:45 amYWG - STL
2 stops8h 46mAir Canada
Wed 3/1910:03 amSTL - YWG
1 stop5h 25mAir Canada
Deal found 2/19$569
This FlightHub deal was found by Cheapflights users on 2/18. 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.
Thu 3/138:25 pmYWG - STL
2 stops20h 27mWestJet
Wed 3/191:48 pmSTL - YWG
2 stops21h 34mWestJet
Deal found 2/18$611

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 February 20, 2025.

Fly from

Winnipeg

Fly to

Illinois

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/21

7:30 am-8:44 am

1 stop25h 14m

Chicago O'Hare Intl

Mon 3/24

8:33 pm-3:08 pm

1 stop18h 35m

$247

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 3/6

8:15 am-3:56 pm

1 stop7h 41m

Chicago O'Hare Intl

Mon 3/10

4:45 pm-12:44 am

1 stop7h 59m

$248

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 3/21

5:00 am-4:40 pm

1 stop11h 40m

Chicago Midway

Mon 3/24

6:20 am-3:08 pm

1 stop8h 48m

$350

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 4/26

2:20 pm-4:48 pm

Nonstop2h 28m

Chicago O'Hare Intl

Wed 4/30

12:57 pm-3:31 pm

Nonstop2h 34m

$380

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 4/10

2:20 pm-4:48 pm

Nonstop2h 28m

Chicago O'Hare Intl

Mon 4/14

7:10 am-1:09 pm

1 stop5h 59m

$445

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 4/10

6:50 am-12:35 pm

2 stops5h 45m

Chicago Midway

Mon 4/14

1:16 pm-8:19 pm

1 stop7h 03m

$452

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 4/26

8:00 am-2:22 pm

1 stop6h 22m

Chicago Midway

Wed 4/30

12:48 pm-4:28 pm

1 stop27h 40m

$484

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 5/13

6:55 pm-4:24 pm

1 stop21h 29m

Chicago Midway

Sat 5/17

9:15 am-10:50 am

1 stop25h 35m

$490

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Sun 4/6

8:50 am-11:30 pm

2 stops14h 40m

Lambert-St Louis

Sat 5/3

5:33 pm-11:28 pm

1 stop5h 55m

$562

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Thu 3/13

6:45 am-3:31 pm

2 stops8h 46m

Lambert-St Louis

Wed 3/19

10:03 am-3:28 pm

1 stop5h 25m

$569

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 20 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.

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 $321). 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 February 20, 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 February 20, 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 February 20, 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
8,219 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

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
8,219 reviews
Delta
8.0
Very good
8,219 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

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
8,219 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

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
8,765 reviews
Delta
8.0
Very good
8,219 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

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
2,801 reviews
Delta
8.0
Very good
8,219 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

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
8,748 reviews
Delta
8.0
Very good
8,219 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

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 $172 on WestJet. Other airlines that offer cheap prices include Air Canada from $214 and Porter Airlines from $219 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 (66%), Air Canada (66%) and United Airlines (66%).

  • What are the cheapest flights from Winnipeg to Illinois?

    Looking for the cheapest flight from Winnipeg to Illinois? While on average our users pay $556, our data indicates the cheapest price to be $149. The most popular route (Winnipeg - Chicago O'Hare Intl), is priced around $210.

  • 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 $321). 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

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$349Average$572FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$443Average$547FlexibilityNo cancel feeOn-time69%
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