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Cheap flights from Winnipeg to Illinois from C$ 172

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 15/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
11 oct. — 18 oct.1
1 adult
1 adult, Economy

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 11 septiembre 2025.

Round-trip from

C$ 312

One-way from

C$ 172

Popular in

April

Cheapest in

September

Average price

C$ 547

Good round-trip deal

C$ 546 or less

Good one-way deal

C$ 587 or less
25/10-26/10
  • 25/10-26/10
  • 3 total stops
  • 25h 04m total
  • Winnipeg to Illinois
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15/12
  • 15/12
  • 2 total stops
  • 24h 32m total
  • Winnipeg to Illinois
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 34 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 14 potential savings vs. average RT price).
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Average for round-trip flights in September 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 11 septiembre 2025.

sáb. 25/106:30 a.m.YWG - MDW
2 stops16h 17mMultiple Airlines
dom. 26/106:20 a.m.MDW - YWG
1 stop8h 47mMultiple Airlines
Deal found 10/9C$ 312
vie. 3/106:15 p.m.YWG - ORD
1 stop18h 24mWestJet
dom. 5/105:30 p.m.ORD - YWG
1 stop15h 31mWestJet
Deal found 9/9C$ 327
sáb. 25/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
dom. 26/102:20 p.m.ORD - YWG
1 stop29h 46mWestJet
Deal found 10/9C$ 328
mié. 1/1011:20 a.m.YWG - ORD
2 stops32h 24mMultiple Airlines
lun. 6/105:30 p.m.ORD - YWG
1 stop15h 31mMultiple Airlines
Deal found 9/9C$ 351
sáb. 18/106:30 a.m.YWG - ORD
1 stop10h 13mWestJet
jue. 23/105:30 p.m.ORD - YWG
1 stop29h 40mWestJet
Deal found 10/9C$ 363
mar. 7/105:10 p.m.YWG - MDW
1 stop15h 29mMultiple Airlines
mar. 14/108:05 a.m.MDW - YWG
2 stops30h 08mMultiple Airlines
Deal found 9/9C$ 371
jue. 9/109:00 a.m.YWG - ORD
1 stop14h 39mMultiple Airlines
jue. 16/105:05 a.m.ORD - YWG
1 stop11h 17mMultiple Airlines
Deal found 11/9C$ 374
dom. 26/107:30 a.m.YWG - MDW
2 stops27h 47mMultiple Airlines
dom. 2/115:20 a.m.MDW - YWG
1 stop8h 47mMultiple Airlines
Deal found 11/9C$ 376
dom. 26/106:15 a.m.YWG - ORD
1 stop7h 20mMultiple Airlines
dom. 2/116:06 p.m.ORD - YWG
2 stops30h 29mMultiple Airlines
Deal found 11/9C$ 381
jue. 2/106:15 p.m.YWG - ORD
2 stops22h 28mWestJet
dom. 5/105:30 p.m.ORD - YWG
1 stop15h 31mWestJet
Deal found 10/9C$ 382
jue. 9/109:00 a.m.YWG - MDW
1 stop14h 46mMultiple Airlines
dom. 12/106:20 a.m.MDW - YWG
2 stops18h 10mMultiple Airlines
Deal found 11/9C$ 385
vie. 17/109:00 a.m.YWG - MDW
1 stop14h 46mMultiple Airlines
dom. 19/106:20 a.m.MDW - YWG
2 stops18h 10mMultiple Airlines
Deal found 11/9C$ 399

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 629,999 searches. Data last updated 11 septiembre 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 - MDW

YWGMDW

Winnipeg

sáb. 25/10

6:30 a.m.-10:47 p.m.

2 stops16h 17m

Chicago Midway

dom. 26/10

6:20 a.m.-3:07 p.m.

1 stop8h 47m

C$ 312

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

vie. 3/10

6:15 p.m.-12:39 p.m.

1 stop18h 24m

Chicago O'Hare Intl

dom. 5/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 327

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

mar. 7/10

5:10 p.m.-8:39 a.m.

1 stop15h 29m

Chicago Midway

mar. 14/10

8:05 a.m.-2:13 p.m.

2 stops30h 08m

C$ 371

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

jue. 9/10

9:00 a.m.-11:39 p.m.

1 stop14h 39m

Chicago O'Hare Intl

jue. 16/10

5:05 a.m.-4:22 p.m.

1 stop11h 17m

C$ 374

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

dom. 26/10

7:30 a.m.-11:17 a.m.

2 stops27h 47m

Chicago Midway

dom. 2/11

5:20 a.m.-2:07 p.m.

1 stop8h 47m

C$ 376

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

jue. 2/10

6:15 p.m.-4:43 p.m.

2 stops22h 28m

Chicago O'Hare Intl

dom. 5/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 382

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

sáb. 4/10

9:10 a.m.-9:58 p.m.

1 stop12h 48m

Chicago O'Hare Intl

dom. 5/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

C$ 389

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

vie. 17/10

4:30 p.m.-4:43 p.m.

2 stops24h 13m

Chicago O'Hare Intl

dom. 19/10

5:30 p.m.-11:41 a.m.

1 stop18h 11m

C$ 392

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

vie. 17/10

9:00 a.m.-11:46 p.m.

1 stop14h 46m

Chicago Midway

dom. 19/10

6:20 a.m.-12:30 a.m.

2 stops18h 10m

C$ 399

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

lun. 29/9

9:00 a.m.-5:26 p.m.

1 stop8h 26m

Chicago O'Hare Intl

mar. 30/9

5:30 p.m.-2:30 p.m.

1 stop21h 00m

C$ 400

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

Showing 1-10 of 33 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.

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, January is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 261). Flying from Winnipeg to Illinois in March is currently the most expensive (average of C$ 349). 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 11 septiembre 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 11 septiembre 2025.

The most flights from YWG to USIL are scheduled on a Wednesday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

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 11 septiembre 2025.
See what other customers who have flown with United Airlines,WestJet, andAir Canada from Winnipeg to Illinois have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,937 reviews
Check prices

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,937 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
WestJet
7.2
Good
3,091 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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?

    If you book a flight to Illinois from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg.

  • How long is the flight from Winnipeg to Illinois?

    Departing from Winnipeg to Illinois will take you 18h 24m. The distance between Winnipeg and Illinois is about 1136 km.

  • What are the most reliable airlines from Winnipeg to Illinois?

    Consider Copa Airlines (84%), Avianca (82%) or SkyWest Airlines (77%) when booking your flight. These represent the most reliable airlines when flying from Winnipeg to Illinois.

  • What are the cheapest flights from Winnipeg to Illinois?

    While on average a flight from Winnipeg to Illinois is generally C$ 1,359, our data shows the cheapest flight currently is C$ 243. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 292 for that flight.

  • 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, January is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 261). Flying from Winnipeg to Illinois in March is currently the most expensive (average of C$ 349). 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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Alternative routes for Winnipeg to Illinois

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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 629,999 searches. Data last updated 11 septiembre 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 200AverageC$ 460FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 362AverageC$ 604FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 488AverageC$ 630FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Illinois?

Cheapflights helps you search for flights from Winnipeg to Illinois via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Illinois?

Cheapflights helps you find that perfect flight to Illinois from Winnipeg by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Winnipeg to Illinois with no change fees?

Certainly. Search results for flights to Illinois from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Winnipeg to Illinois become cheaper?

Of course! You can now track prices for flights from Winnipeg to Illinois and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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