How long is the flight from Illinois to Winnipeg?

Airlines like WestJet, Porter Airlines, and Delta fly from Illinois to Winnipeg in about 7h 25m. The time it takes to get you to your destination can typically vary by up to 23h. There are 1136 km between Illinois and Winnipeg. This flight may include one or multiple stops.

In terms of precipitation, rainfall in Winnipeg ranges from 20.0 - 80.0 mm per month. June is typically the wettest month, when rainfall can reach 80.0 mm. January is typically the driest time to visit Winnipeg when rainfall is around 20.0 mm.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 20.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -16.0 C).

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 cheapest flights from Illinois to Winnipeg?

On average you can expect to pay C$ 539 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 464 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 496.

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 (73%), SkyWest Airlines (63%) and Air Canada (63%).

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.

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.

C$ 202+ Cheap Flights from Illinois to Winnipeg

Cheap flight deals from Illinois to Winnipeg

Enter your travel dates to find the best prices.

Cheapest

Best

Direct

Last-minute

One-way

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 23 August 2026.

Fri 2/105:30 p.m. -

1 stop7h 25m

Sun 4/107:00 a.m. -

1 stop9h 40m

Deal found 22/8C$ 416

Thu 8/105:30 p.m. -

1 stop7h 25m

Sun 11/107:00 a.m. -

1 stop9h 40m

Deal found 19/8C$ 419

Thu 17/95:30 p.m. -

1 stop7h 25m

Sun 20/97:00 a.m. -

1 stop9h 40m

Deal found 22/8C$ 420

Wed 2/95:30 p.m. -

1 stop7h 25m

Sat 5/97:00 a.m. -

1 stop9h 40m

Deal found 20/8C$ 435

Thu 24/911:45 a.m. -

1 stop9h 00m

Mon 28/911:15 a.m. -

2 stops23h 45m

Deal found 21/8C$ 463

Mon 21/95:30 p.m. -

1 stop7h 25m

Mon 28/97:45 a.m. -

2 stops31h 35m

Deal found 22/8C$ 481

Mon 5/105:30 p.m. -

1 stop7h 25m

Mon 12/105:00 p.m. -

2 stops37h 34m

Deal found 21/8C$ 494

Thu 8/105:30 p.m. -

1 stop7h 25m

Mon 12/105:00 p.m. -

2 stops37h 34m

Deal found 21/8C$ 500

Fri 18/93:20 p.m. -

1 stop9h 35m

Sun 20/96:15 a.m. -

1 stop8h 20m

Deal found 19/8C$ 527

Thu 8/1011:45 a.m. -

1 stop9h 00m

Sun 11/1011:15 a.m. -

2 stops23h 45m

Deal found 19/8C$ 695

Sun 27/129:23 p.m. -

1 stop17h 17m

Thu 31/128:35 p.m. -

2 stops16h 24m

Deal found 21/8C$ 825

Fri 13/119:45 a.m. -

1 stop6h 59m

Sat 21/115:35 p.m. -

1 stop5h 48m

Deal found 20/8C$ 832

Best flights from Illinois to Winnipeg
Discover carefully curated flight deals from Illinois to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 23 August 2026.

Wed 2/95:30 p.m. -

1 stop7h 25m

Sat 5/97:00 a.m. -

1 stop9h 40m

Deal found 23/8C$ 454

Mon 5/105:30 p.m. -

1 stop7h 25m

Wed 7/106:00 a.m. -

2 stops24h 34m

Deal found 18/8C$ 642

Wed 11/1111:45 a.m. -

2 stops30h 25m

Mon 16/117:00 a.m. -

1 stop7h 37m

Deal found 18/8C$ 854

Sun 4/103:11 p.m. -

1 stop7h 22m

Sun 11/107:00 a.m. -

1 stop8h 43m

Deal found 20/8C$ 1,055

Sun 13/912:10 p.m. -

2 stops11h 07m

Thu 17/98:15 a.m. -

1 stop5h 45m

Deal found 19/8C$ 1,068

Wed 4/111:27 p.m. -

2 stops9h 52m

Wed 11/116:35 a.m. -

1 stop5h 15m

Deal found 23/8C$ 1,093

Fri 13/119:45 a.m. -

1 stop6h 59m

Sat 21/115:35 p.m. -

1 stop5h 48m

Deal found 20/8C$ 832

Mon 28/911:42 a.m. -

1 stop8h 07m

Tue 29/99:20 a.m. -

1 stop10h 10m

Deal found 19/8C$ 876

Wed 14/101:55 p.m. -

2 stops11h 00m

Tue 20/109:20 a.m. -

1 stop6h 59m

Deal found 18/8C$ 944

Wed 28/1011:45 a.m. -

2 stops30h 25m

Mon 2/117:00 a.m. -

1 stop7h 37m

Deal found 23/8C$ 964

Tue 8/99:18 p.m. -

1 stop19h 09m

Fri 11/95:00 a.m. -

1 stop6h 21m

Deal found 20/8C$ 1,082

Wed 2/99:59 a.m. -

1 stop5h 09m

Sat 5/96:40 a.m. -

2 stops10h 19m

Deal found 20/8C$ 1,234

Wed 16/99:45 a.m. -

2 stops24h 35m

Wed 23/911:40 a.m. -

2 stops8h 40m

Deal found 21/8C$ 1,023

Fri 4/91:25 p.m. -

2 stops11h 30m

Fri 5/25:38 p.m. -

1 stop23h 12m

Deal found 18/8C$ 1,162

Sat 26/93:20 p.m. -

2 stops26h 38m

Tue 29/911:15 a.m. -

2 stops23h 45m

Deal found 21/8C$ 1,026

Wed 23/126:00 a.m. -

1 stop8h 40m

Mon 4/17:00 a.m. -

1 stop9h 25m

Deal found 21/8C$ 1,313

Thu 21/19:55 a.m. -

1 stop7h 05m

Sun 24/16:35 a.m. -

1 stop5h 16m

Deal found 20/8C$ 1,315

Tue 6/1011:45 a.m. -

2 stops22h 58m

Tue 13/1011:15 a.m. -

2 stops27h 05m

Deal found 22/8C$ 1,187

Mon 5/109:59 a.m. -

1 stop5h 09m

Mon 12/106:40 a.m. -

2 stops6h 07m

Deal found 21/8C$ 1,329

Thu 24/96:05 a.m. -

2 stops9h 03m

Mon 28/912:41 p.m. -

2 stops10h 03m

Deal found 23/8C$ 1,336

Find flight deals from Illinois to Winnipeg

Round-trip from	C$ 416
One-way from	C$ 202
Popular in	August
Cheapest in	February
Average price	C$ 1,729
Good one-way deal	C$ 464 or less

WestJet
2/10-4/10
2 total stops
17h 05m total
Illinois to Winnipeg

Search Deals

WestJet
18/9
1 total stop
7h 25m total
Illinois to Winnipeg

Search Deals

Highest demand for flights based on searches. 25% potential increase in price (C$ 497 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 7% potential price decrease (C$ 97 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in August 2026

Search Deals

Price to beat on a one-way flight from Illinois to Winnipeg.

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 2/9

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sat 5/9

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

1 stop9h 40m

C$ 454

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 5/10

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Wed 7/10

6:00 a.m.-6:34 a.m.

2 stops24h 34m

C$ 642

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Fri 13/11

9:45 a.m.-4:44 p.m.

1 stop6h 59m

Winnipeg

Sat 21/11

5:35 p.m.-11:23 p.m.

1 stop5h 48m

C$ 832

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 11/11

11:45 a.m.-6:10 p.m.

2 stops30h 25m

Winnipeg

Mon 16/11

7:00 a.m.-2:37 p.m.

1 stop7h 37m

C$ 854

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 28/9

11:42 a.m.-7:49 p.m.

1 stop8h 07m

Winnipeg

Tue 29/9

9:20 a.m.-7:30 p.m.

1 stop10h 10m

C$ 876

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 14/10

1:55 p.m.-12:55 a.m.

2 stops11h 00m

Winnipeg

Tue 20/10

9:20 a.m.-4:19 p.m.

1 stop6h 59m

C$ 944

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 28/10

11:45 a.m.-6:10 p.m.

2 stops30h 25m

Winnipeg

Mon 2/11

7:00 a.m.-2:37 p.m.

1 stop7h 37m

C$ 964

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 16/9

9:45 a.m.-10:20 a.m.

2 stops24h 35m

Winnipeg

Wed 23/9

11:40 a.m.-8:20 p.m.

2 stops8h 40m

C$ 1,023

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Sat 26/9

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

2 stops26h 38m

Winnipeg

Tue 29/9

11:15 a.m.-11:00 a.m.

2 stops23h 45m

C$ 1,026

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Sun 4/10

3:11 p.m.-10:33 p.m.

1 stop7h 22m

Winnipeg

Sun 11/10

7:00 a.m.-3:43 p.m.

1 stop8h 43m

C$ 1,055

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/8

Showing 1-10 of 39 resultsSorted by cheapest first

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.

ORD-YWG

MDW-YWG

STL-YWG

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

USIL-YWG

ORD-YWG

MDW-YWG

STL-YWG

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

Currently, September is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 571). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,695). 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 (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

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

Airfare is below average for this route at the moment.

Illinois to Winnipeg flights typically cost between C$ 631 and C$ 1,380 in October.
The cheapest round-trip price found within the last 5 days was C$ 416 on WestJet (2 Oct-4 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 WestJet, Porter Airlines, and Delta fly from Illinois to Winnipeg in about 7h 25m. The time it takes to get you to your destination can typically vary by up to 23h. 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 (73%), SkyWest Airlines (63%) and Air Canada (63%).
What are the cheapest flights from Illinois to Winnipeg?
On average you can expect to pay C$ 539 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 464 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 496.
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, September is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 571). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,695). 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.

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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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Cheap flights from Illinois to Winnipeg from C$ 202

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 18/9. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Illinois to Winnipeg

Cheapest flights from Illinois to WinnipegExplore 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 23 August 2026.

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 23 August 2026.

Best flights from Illinois to WinnipegDiscover carefully curated flight deals from Illinois to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 23 August 2026.

Discover carefully curated flight deals from Illinois to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 23 August 2026.

Direct flights from Illinois to WinnipegExplore direct flight options from Illinois to Winnipeg based on user searches, and compare prices and availability for your desired travel dates. Data last updated 23 August 2026.

Explore direct flight options from Illinois to Winnipeg based on user searches, and compare prices and availability for your desired travel dates. Data last updated 23 August 2026.

Last-minute flights from Illinois to WinnipegDiscover last-minute flight deals from Illinois to Winnipeg. Data last updated 23 August 2026 and is based on user searches.

Discover last-minute flight deals from Illinois to Winnipeg. Data last updated 23 August 2026 and is based on user searches.

One-way flights from Illinois to WinnipegSearch for one-way flight options from Illinois to Winnipeg. Find affordable one-way fares based on user searches. Data last updated 23 August 2026.

Search for one-way flight options from Illinois to Winnipeg. Find affordable one-way fares based on user searches. Data last updated 23 August 2026.

Find flight deals from Illinois to Winnipeg

Round-trip from

One-way from

Popular in

Cheapest in

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Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

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.

Cheapflights Insights

What is the cheapest month to book a 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 23 August 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 23 August 2026.

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

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

Airfare is below average for this route at the moment.

Illinois to Winnipeg flights typically cost between C$ 631 and C$ 1,380 in October.The cheapest round-trip price found within the last 5 days was C$ 416 on WestJet (2 Oct-4 Oct).

Related info for your journey

What airport do you fly into for flights to Winnipeg from Illinois?

How long is the flight from Illinois to Winnipeg?

What are the most popular routes from Illinois to Winnipeg?

What are the most reliable airlines from Illinois to Winnipeg?

What are the cheapest flights from Illinois to Winnipeg?

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

How can I find direct flights from Illinois to Winnipeg?

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

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

Travelling to a place near Winnipeg?

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Illinois and Winnipeg flights

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

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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 23 August 2026.

Best flights from Illinois to Winnipeg
Discover carefully curated flight deals from Illinois to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 23 August 2026.

Direct flights from Illinois to Winnipeg
Explore direct flight options from Illinois to Winnipeg based on user searches, and compare prices and availability for your desired travel dates. Data last updated 23 August 2026.

Last-minute flights from Illinois to Winnipeg
Discover last-minute flight deals from Illinois to Winnipeg. Data last updated 23 August 2026 and is based on user searches.

One-way flights from Illinois to Winnipeg
Search for one-way flight options from Illinois to Winnipeg. Find affordable one-way fares based on user searches. Data last updated 23 August 2026.

Illinois to Winnipeg flights typically cost between C$ 631 and C$ 1,380 in October.
The cheapest round-trip price found within the last 5 days was C$ 416 on WestJet (2 Oct-4 Oct).