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Cheap flights from Illinois to Winnipeg from C$ 186

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 15/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
2 May — 9 May1
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 2 April 2026.

Thu 23/411:28 a.m.
ORD
-
YWG
1 stop27h 41m
Multiple Airlines
Mon 27/49:05 p.m.
YWG
-
ORD
2 stops13h 18m
Multiple Airlines
Deal found 30/3C$ 439
Wed 10/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 13/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 29/3C$ 447
Thu 7/56:50 a.m.
ORD
-
YWG
2 stops15h 20m
Multiple Airlines
Sun 10/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 30/3C$ 451
Mon 27/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 4/59:05 p.m.
YWG
-
ORD
2 stops22h 46m
Multiple Airlines
Deal found 29/3C$ 472
Thu 7/56:00 a.m.
MDW
-
YWG
2 stops16h 10m
Multiple Airlines
Sun 10/54:25 p.m.
YWG
-
MDW
1 stop17h 20m
Multiple Airlines
Deal found 29/3C$ 485
Fri 8/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sat 16/59:05 p.m.
YWG
-
ORD
2 stops34h 50m
Multiple Airlines
Deal found 29/3C$ 490
Sat 13/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 22/69:05 p.m.
YWG
-
ORD
2 stops13h 17m
Multiple Airlines
Deal found 29/3C$ 496
Wed 13/51:18 p.m.
ORD
-
YWG
2 stops35h 37m
Multiple Airlines
Wed 20/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 29/3C$ 513
Sat 16/57:05 a.m.
STL
-
YWG
1 stop7h 13m
Air Canada
Sat 23/511:00 a.m.
YWG
-
STL
1 stop9h 25m
Air Canada
Deal found 1/4C$ 518
Thu 7/53:20 p.m.
MDW
-
YWG
1 stop23h 59m
Porter Airlines
Sun 10/57:00 p.m.
YWG
-
MDW
1 stop14h 45m
Porter Airlines
Deal found 29/3C$ 554
Thu 14/58:30 p.m.
STL
-
YWG
1 stop15h 22m
United Airlines
Wed 20/52:00 p.m.
YWG
-
STL
1 stop7h 18m
United Airlines
Deal found 31/3C$ 603
Thu 14/58:30 p.m.
STL
-
YWG
1 stop15h 22m
United Airlines
Mon 18/52:00 p.m.
YWG
-
STL
1 stop7h 13m
United Airlines
Deal found 30/3C$ 604

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 2 April 2026.

Round-trip from

C$ 439

One-way from

C$ 186

Popular in

January

Cheapest in

May

Average price

C$ 758

Good one-way deal

C$ 484 or less
23/4-27/4
  • 23/4-27/4
  • 3 total stops
  • 40h 59m total
  • Illinois to Winnipeg
Search Deals
15/4
  • 15/4
  • 2 total stops
  • 13h 12m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 354 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease (C$ 113 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a one-way flight from Illinois to Winnipeg.
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 2 April 2026.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 7/5

6:50 a.m.-10:10 p.m.

2 stops15h 20m

Winnipeg

Sun 10/5

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 456

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 25/5

5:10 a.m.-8:57 p.m.

1 stop15h 47m

Winnipeg

Mon 1/6

7:00 a.m.-9:16 p.m.

1 stop14h 16m

C$ 603

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 2/6

5:10 a.m.-8:57 p.m.

1 stop15h 47m

Winnipeg

Wed 3/6

2:00 p.m.-9:16 p.m.

1 stop7h 16m

C$ 603

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 14/5

8:30 p.m.-11:52 a.m.

1 stop15h 22m

Winnipeg

Wed 20/5

2:00 p.m.-9:18 p.m.

1 stop7h 18m

C$ 603

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 14/5

8:30 p.m.-11:52 a.m.

1 stop15h 22m

Winnipeg

Mon 18/5

2:00 p.m.-9:13 p.m.

1 stop7h 13m

C$ 603

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 14/4

2:15 p.m.-3:09 p.m.

1 stop24h 54m

Winnipeg

Fri 17/4

9:05 p.m.-6:37 p.m.

2 stops21h 32m

C$ 808

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/5

11:48 a.m.-7:49 p.m.

1 stop8h 01m

Winnipeg

Wed 6/5

9:20 a.m.-4:18 p.m.

1 stop6h 58m

C$ 867

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 4/6

6:24 a.m.-11:26 p.m.

1 stop17h 02m

Winnipeg

Mon 8/6

6:40 a.m.-8:31 p.m.

2 stops13h 51m

C$ 981

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 13/5

10:30 a.m.-11:18 p.m.

2 stops12h 48m

Winnipeg

Wed 20/5

5:10 a.m.-10:20 p.m.

2 stops17h 10m

C$ 988

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 18/8

2:00 p.m.-11:27 p.m.

1 stop9h 27m

Winnipeg

Mon 24/8

6:40 a.m.-1:11 p.m.

1 stop6h 31m

C$ 995

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/3

Showing 1-10 of 48 resultsSorted by cheapest first
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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 2 April 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 2 April 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).

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

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 United Airlines, Porter Airlines, and Delta fly from Illinois to Winnipeg in about 8h 01m. The time it takes to get you to your destination can typically vary by up to 7h 46m. There are 1136 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 (64%), Air Canada (64%) and United Airlines (64%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 495 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 229 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 553.

  • 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

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Alternative routes for Illinois to Winnipeg

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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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