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Cheap flights from Illinois to Winnipeg from C$ 188

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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
20 Feb — 27 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Illinois to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Illinois to Winnipeg
Explore the most affordable flight options available from Illinois to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 21 January 2026.

Tue 17/26:00 a.m.
MDW
-
YWG
2 stops36h 05m
Multiple Airlines
Tue 24/28:05 p.m.
YWG
-
MDW
1 stop14h 05m
Multiple Airlines
Deal found 19/1C$ 400
Tue 17/26:02 p.m.
ORD
-
YWG
2 stops24h 03m
Multiple Airlines
Tue 24/28:00 a.m.
YWG
-
ORD
1 stop31h 52m
Multiple Airlines
Deal found 19/1C$ 413
Fri 5/65:30 p.m.
ORD
-
YWG
2 stops17h 55m
WestJet
Sun 7/67:00 a.m.
YWG
-
ORD
2 stops9h 43m
WestJet
Deal found 20/1C$ 460
Fri 6/36:00 a.m.
MDW
-
YWG
1 stop9h 09m
Multiple Airlines
Fri 13/37:30 a.m.
YWG
-
MDW
1 stop12h 17m
Multiple Airlines
Deal found 19/1C$ 471
Fri 6/35:05 a.m.
ORD
-
YWG
1 stop10h 04m
Multiple Airlines
Fri 13/37:30 a.m.
YWG
-
ORD
1 stop15h 09m
Multiple Airlines
Deal found 19/1C$ 480
Mon 2/33:50 p.m.
ORD
-
YWG
2 stops19h 42m
Multiple Airlines
Wed 4/37:30 a.m.
YWG
-
ORD
1 stop9h 22m
Multiple Airlines
Deal found 20/1C$ 495
Fri 15/55:30 p.m.
ORD
-
YWG
1 stop21h 00m
WestJet
Sat 23/58:30 a.m.
YWG
-
ORD
1 stop8h 13m
WestJet
Deal found 20/1C$ 496
Tue 3/37:30 a.m.
MDW
-
YWG
2 stops17h 10m
Multiple Airlines
Wed 4/37:30 a.m.
YWG
-
MDW
1 stop11h 37m
Multiple Airlines
Deal found 21/1C$ 505
Tue 17/36:25 a.m.
STL
-
YWG
1 stop5h 32m
United Airlines
Wed 18/32:20 p.m.
YWG
-
STL
1 stop6h 47m
United Airlines
Deal found 20/1C$ 574
Mon 2/34:05 p.m.
STL
-
YWG
1 stop7h 49m
Air Canada
Wed 4/37:05 a.m.
YWG
-
STL
1 stop8h 24m
Air Canada
Deal found 21/1C$ 577
Mon 2/39:50 a.m.
MDW
-
YWG
2 stops9h 45m
Multiple Airlines
Wed 4/37:30 a.m.
YWG
-
MDW
1 stop11h 37m
Multiple Airlines
Deal found 20/1C$ 585
Thu 14/56:30 a.m.
STL
-
YWG
2 stops14h 55m
WestJet
Wed 20/55:38 p.m.
YWG
-
STL
1 stop5h 23m
WestJet
Deal found 20/1C$ 596

Find flight deals from Illinois to Winnipeg

Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated 21 January 2026.

Round-trip from

C$ 400

One-way from

C$ 188

Popular in

January

Cheapest in

May

Average price

C$ 1,702
17/2-24/2
  • 17/2-24/2
  • 3 total stops
  • 50h 10m total
  • Illinois to Winnipeg
Search Deals
2/3
  • 2/3
  • 2 total stops
  • 27h 20m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 30% potential increase in price (C$ 523 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease (C$ 106 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Winnipeg 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 21 January 2026.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Illinois

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 17/2

6:00 a.m.-6:05 p.m.

2 stops36h 05m

Winnipeg

Tue 24/2

8:05 p.m.-10:10 a.m.

1 stop14h 05m

C$ 400

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 6/3

6:00 a.m.-3:09 p.m.

1 stop9h 09m

Winnipeg

Fri 13/3

7:30 a.m.-7:47 p.m.

1 stop12h 17m

C$ 471

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 6/3

5:05 a.m.-3:09 p.m.

1 stop10h 04m

Winnipeg

Fri 13/3

7:30 a.m.-10:39 p.m.

1 stop15h 09m

C$ 480

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-11:10 p.m.

2 stops29h 40m

Winnipeg

Sun 7/6

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

1 stop8h 13m

C$ 481

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 2/3

2:20 p.m.-10:07 a.m.

1 stop19h 47m

Winnipeg

Wed 4/3

12:10 p.m.-7:17 p.m.

1 stop7h 07m

C$ 502

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 3/3

7:30 a.m.-12:40 a.m.

2 stops17h 10m

Winnipeg

Wed 4/3

7:30 a.m.-7:07 p.m.

1 stop11h 37m

C$ 505

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 17/2

4:43 p.m.-12:40 a.m.

3 stops31h 57m

Winnipeg

Tue 24/2

5:00 a.m.-11:47 p.m.

2 stops18h 47m

C$ 513

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 11/5

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

1 stop21h 00m

Winnipeg

Mon 1/6

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

1 stop8h 13m

C$ 550

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 17/3

6:25 a.m.-11:57 a.m.

1 stop5h 32m

Winnipeg

Wed 18/3

2:20 p.m.-9:07 p.m.

1 stop6h 47m

C$ 574

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 7/3

4:05 p.m.-11:54 p.m.

1 stop7h 49m

Winnipeg

Sat 14/3

7:05 a.m.-3:29 p.m.

1 stop8h 24m

C$ 577

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/1

Showing 1-10 of 37 results
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Best time to book a flight from Illinois to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Illinois 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 Illinois to Winnipeg

What is the cheapest time of day to fly from IL to YWG?

Find hourly flight availability from Illinois to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 21 January 2026.

When flying from Illinois to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Illinois to Winnipeg

Explore weekly flight availability from Illinois to Winnipeg. 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 21 January 2026.

The most flights from USIL to YWG 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).

Related info for your journey

Find useful and relevant information for your journey from Illinois to Winnipeg. 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 into for flights to Winnipeg from Illinois?

    Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly into when you book flights from Illinois to Winnipeg.

  • How long is the flight from Illinois to Winnipeg?

    Airlines like WestJet, United Airlines, and Air Canada fly from Illinois to Winnipeg in about 5h 32m. The time it takes to get you to your destination can typically vary by up to 24h 08m. There are 1353 km between Illinois and Winnipeg. This flight may include one or multiple stops.

  • What are the most popular routes from Illinois to Winnipeg?

    The most popular route from Illinois to Winnipeg is Chicago O'Hare Intl - Winnipeg. You may also consider Chicago Midway - Winnipeg or Lambert-St Louis - Winnipeg.

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

    The top 3 most reliable airlines when flying from Illinois to Winnipeg are SkyWest Airlines (54%), Air Canada (54%) and United Airlines (54%).

  • Can I find deals for flights from Illinois to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Illinois to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Winnipeg.

  • Can I find deals for business class flights from Illinois to Winnipeg?

    Yes. Cheapflights offers flight deals from Illinois to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Portage la Prairie

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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 Illinois to Winnipeg?

Cheapflights makes it easy to find Illinois to Winnipeg flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Winnipeg from Illinois.

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

Yes! Cheapflights helps users easily find flights from Illinois to Winnipeg with no change fees.

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

Yes! Start tracking prices for Illinois to Winnipeg flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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