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Cheap flights from Illinois to Winnipeg from C$ 175

ORD — YWG
14 Oct — 21 Oct1
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

Thu 15/105:30 p.m. -
1 stop7h 25m
Sun 18/107:00 a.m. -
1 stop9h 40m
Deal found 10/9C$ 454
Sun 11/105:30 p.m. -
1 stop7h 25m
Sun 18/107:00 a.m. -
1 stop9h 40m
Deal found 13/9C$ 462
Fri 9/103:20 p.m. -
1 stop18h 25m
Mon 12/107:45 a.m. -
1 stop27h 15m
Deal found 12/9C$ 479
Wed 30/93:20 p.m. -
1 stop18h 25m
Fri 2/106:05 p.m. -
1 stop16h 55m
Deal found 10/9C$ 480
Wed 30/93:20 p.m. -
1 stop18h 25m
Sat 3/104:15 p.m. -
2 stops18h 45m
Deal found 10/9C$ 483
Tue 29/93:20 p.m. -
2 stops19h 23m
Fri 2/107:55 p.m. -
1 stop15h 05m
Deal found 10/9C$ 487
Thu 15/108:04 a.m. -
2 stops16h 51m
Mon 19/107:00 a.m. -
1 stop9h 40m
Deal found 10/9C$ 501
Thu 1/103:20 p.m. -
1 stop17h 20m
Sat 3/104:25 p.m. -
1 stop18h 35m
Deal found 13/9C$ 508
Thu 15/105:30 p.m. -
1 stop7h 25m
Wed 21/107:10 p.m. -
1 stop21h 30m
Deal found 10/9C$ 512
Thu 15/108:04 a.m. -
2 stops16h 51m
Sun 18/107:00 a.m. -
1 stop9h 40m
Deal found 12/9C$ 520
Fri 23/105:30 p.m. -
1 stop7h 25m
Mon 26/109:35 p.m. -
2 stops15h 16m
Deal found 9/9C$ 528
Wed 28/106:20 p.m. -
2 stops23h 50m
Sun 1/115:00 a.m. -
1 stop12h 40m
Deal found 12/9C$ 530

Find flight deals from Illinois to Winnipeg

Round-trip from

C$ 454

One-way from

C$ 175

Popular in

August

Cheapest in

February

Average price

C$ 710
WestJet
  • WestJet
  • 15/10-19/10
  • 2 total stops
  • 17h 05m total
  • Illinois to Winnipeg
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26/10-31/12
  • 26/10-31/12
  • 2 total stops
  • 30h 35m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 289 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease (C$ 120 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Cheapflights Fare Finder

 
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

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Wed 21/10

6:35 p.m.-12:55 a.m.

3 stops30h 20m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 222

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 25/10

6:20 p.m.-9:15 a.m.

1 stop14h 55m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 234

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 18/11

7:28 p.m.-4:25 p.m.

2 stops20h 57m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 252

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 19/10

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

1 stop17h 40m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 264

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 12/11

6:16 a.m.-12:10 a.m.

2 stops17h 54m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 268

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Mon 26/10

6:35 p.m.-12:44 a.m.

3 stops30h 09m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 280

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 23/10

6:15 a.m.-12:55 a.m.

3 stops18h 40m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 286

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 12/11

6:00 a.m.-12:10 a.m.

3 stops18h 10m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 288

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 27/10

6:30 a.m.-5:25 p.m.

3 stops34h 55m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 308

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 2/10

3:20 p.m.-5:58 p.m.

2 stops26h 38m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 311

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 53 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

Cheapflights Insights

Everything you need to know about your flight from Illinois to Winnipeg

What is the cheapest month to book a flight from Illinois to Winnipeg?

Currently, October is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 684). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,707). 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 IL to YWG?

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

The most flights from USIL to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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

Airfare is typical for this route at the moment.
Illinois to Winnipeg flights typically cost between C$ 354 and C$ 1,594 in October.
The cheapest round-trip price found within the last 5 days was C$ 454 on WestJet (15 Oct-19 Oct).

Related info for your journey

  • 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 Air Canada and Porter Airlines fly from Illinois to Winnipeg in about 6h 32m. The time it takes to get you to your destination can typically vary by up to 35m. 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 Copa Airlines (65%), SkyWest Airlines (64%) and Air Canada (64%).

  • 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.

  • What is the cheapest month to book a flight from Illinois to Winnipeg?

    Currently, October is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 684). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,707). 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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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?

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

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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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