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Cheap flights from Winnipeg to Illinois from C$ 169

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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
16 Jan — 23 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Illinois

Enter your travel dates to find the best prices.

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 17 December 2025.

Wed 31/124:55 p.m.YWG - ORD
1 stop27h 28mMultiple Airlines
Sat 4/411:39 a.m.ORD - YWG
2 stops36h 08mMultiple Airlines
Deal found 17/12C$ 725
Wed 31/128:05 p.m.YWG - ORD
2 stops16h 07mWestJet
Sat 4/412:15 p.m.ORD - YWG
2 stops31h 09mWestJet
Deal found 17/12C$ 845
Mon 29/1212:20 p.m.YWG - MDW
2 stops20h 29mWestJet
Mon 5/19:50 a.m.MDW - YWG
1 stop25h 13mWestJet
Deal found 16/12C$ 852
Wed 24/124:55 p.m.YWG - ORD
1 stop27h 28mMultiple Airlines
Wed 31/126:35 a.m.ORD - YWG
2 stops29h 34mMultiple Airlines
Deal found 17/12C$ 864
Mon 29/1212:20 p.m.YWG - ORD
2 stops20h 41mWestJet
Mon 5/17:10 a.m.ORD - YWG
2 stops12h 02mWestJet
Deal found 16/12C$ 875
Wed 24/128:05 p.m.YWG - ORD
2 stops21h 49mWestJet
Wed 31/126:35 a.m.ORD - YWG
2 stops29h 34mWestJet
Deal found 17/12C$ 970
Thu 25/126:45 a.m.YWG - MDW
2 stops10h 34mWestJet
Sun 28/1211:48 a.m.MDW - YWG
1 stop5h 07mWestJet
Deal found 15/12C$ 1,057
Sat 20/1212:20 p.m.YWG - MDW
2 stops23h 38mWestJet
Tue 6/19:50 a.m.MDW - YWG
1 stop25h 13mWestJet
Deal found 14/12C$ 1,075
Wed 24/122:20 p.m.YWG - ORD
Nonstop2h 43mUnited Airlines
Wed 31/123:55 p.m.ORD - YWG
1 stop7h 59mUnited Airlines
Deal found 17/12C$ 1,104
Wed 24/122:20 p.m.YWG - ORD
Nonstop2h 43mAir Canada
Wed 31/129:10 a.m.ORD - YWG
Nonstop2h 47mAir Canada
Deal found 17/12C$ 1,111
Mon 29/124:55 p.m.YWG - MDW
2 stops27h 00mMultiple Airlines
Fri 2/13:10 p.m.MDW - YWG
1 stop10h 16mMultiple Airlines
Deal found 14/12C$ 1,204
Fri 19/125:45 p.m.YWG - MDW
1 stop23h 34mWestJet
Mon 22/129:29 a.m.MDW - YWG
2 stops26h 06mWestJet
Deal found 16/12C$ 1,210

Find flight deals from Winnipeg to Illinois

Keep the following information in mind while searching for Winnipeg to Illinois flight deals. Data was last updated 17 December 2025.

Round-trip from

C$ 283

One-way from

C$ 169

Popular in

December

Cheapest in

September

Average price

C$ 828

Good round-trip deal

C$ 628 or less

Good one-way deal

C$ 485 or less
13/1-20/1
  • 13/1-20/1
  • 3 total stops
  • 44h 06m total
  • Winnipeg to Illinois
Search Deals
12/1
  • 12/1
  • 2 total stops
  • 19h 52m total
  • Winnipeg to Illinois
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 91 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Winnipeg to Illinois.
Search Deals
Price to beat on a one-way flight from Winnipeg to Illinois.
Search Deals

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 17 December 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

Wed 14/1

12:55 p.m.-11:47 a.m.

2 stops22h 52m

Chicago Midway

Mon 19/1

12:57 p.m.-12:43 a.m.

1 stop11h 46m

C$ 289

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 14/1

7:30 a.m.-4:52 p.m.

1 stop9h 22m

Chicago O'Hare Intl

Mon 19/1

11:48 a.m.-12:43 a.m.

1 stop12h 55m

C$ 300

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 16/1

5:05 p.m.-4:52 p.m.

1 stop23h 47m

Chicago O'Hare Intl

Sun 18/1

8:41 p.m.-12:43 a.m.

1 stop28h 02m

C$ 319

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 13/5

3:15 p.m.-4:43 p.m.

1 stop25h 28m

Chicago O'Hare Intl

Mon 18/5

5:30 p.m.-10:00 a.m.

1 stop16h 30m

C$ 322

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 7/6

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Thu 11/6

5:30 p.m.-1:00 p.m.

2 stops19h 30m

C$ 330

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

5:00 p.m.-4:43 p.m.

2 stops23h 43m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-11:00 p.m.

1 stop29h 30m

C$ 330

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 13/1

8:00 a.m.-5:52 p.m.

1 stop9h 52m

Chicago O'Hare Intl

Tue 20/1

2:53 p.m.-3:07 p.m.

1 stop24h 14m

C$ 339

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 13/1

9:00 p.m.-10:31 a.m.

2 stops13h 31m

Chicago Midway

Tue 20/1

1:20 p.m.-3:07 p.m.

1 stop25h 47m

C$ 344

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 12/1

9:00 p.m.-10:34 a.m.

2 stops13h 34m

Chicago Midway

Mon 19/1

12:57 p.m.-12:43 a.m.

1 stop11h 46m

C$ 362

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 16/5

6:30 p.m.-4:43 p.m.

1 stop22h 13m

Chicago O'Hare Intl

Wed 20/5

5:30 p.m.-8:48 p.m.

2 stops27h 18m

C$ 363

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/12

Showing 1-10 of 29 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, May is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 200). Flying from Winnipeg to Illinois in January is currently the most expensive (average of C$ 641). 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 17 December 2025.

A simple way to save on the total cost of your ticket is to fly from Winnipeg to Illinois in the evening. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight in the morning.

How much does it cost to fly round-trip from Winnipeg to Illinois?

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 17 December 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
9,092 reviews
Check prices

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,092 reviews
United Airlines
7.4
Good
9,092 reviews
Check prices

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,202 reviews
United Airlines
7.4
Good
9,092 reviews
Check prices

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,531 reviews
United Airlines
7.4
Good
9,092 reviews
Check prices

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 25h 28m. The distance between Winnipeg and Illinois is about 1136 km.

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

    Consider Copa Airlines (90%), SkyWest Airlines (84%) or Air Canada (84%) 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$ 763, our data shows the cheapest flight currently is C$ 279. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 323 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, May is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 200). Flying from Winnipeg to Illinois in January is currently the most expensive (average of C$ 641). 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 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 17 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 199AverageC$ 409FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 484AverageC$ 641FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 494AverageC$ 728FlexibilityNo cancel feeOn-time67%
Search Air Canada 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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