How long is the flight from Illinois to Winnipeg?

Airlines like Porter Airlines, Air Canada, and WestJet fly from Illinois to Winnipeg in about 7h 16m. The time it takes to get you to your destination can typically vary by up to 15h 39m. 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 most reliable airlines from Illinois to Winnipeg?

The top 3 most reliable airlines when flying from Illinois to Winnipeg are SkyWest Airlines (67%), Air Canada (67%) and United Airlines (67%).

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.

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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 17 September 2026.

Thu 15/105:30 p.m. -

1 stop7h 25m

Mon 19/107:00 a.m. -

1 stop9h 40m

Deal found 16/9C$ 441

Sun 11/105:30 p.m. -

1 stop7h 25m

Sun 18/107:00 a.m. -

1 stop9h 40m

Deal found 13/9C$ 456

Fri 9/103:20 p.m. -

1 stop18h 25m

Mon 12/107:45 a.m. -

1 stop27h 15m

Deal found 12/9C$ 481

Fri 2/105:30 p.m. -

1 stop7h 25m

Mon 5/107:45 a.m. -

2 stops31h 35m

Deal found 15/9C$ 488

Thu 1/105:30 p.m. -

1 stop7h 25m

Wed 7/1010:10 a.m. -

2 stops19h 07m

Deal found 14/9C$ 494

Fri 2/105:30 p.m. -

1 stop7h 25m

Wed 7/1010:10 a.m. -

2 stops19h 07m

Deal found 15/9C$ 495

Thu 1/103:20 p.m. -

1 stop17h 20m

Sat 3/104:25 p.m. -

1 stop18h 35m

Deal found 13/9C$ 510

Thu 15/108:04 a.m. -

2 stops16h 51m

Sun 18/107:00 a.m. -

1 stop9h 40m

Deal found 12/9C$ 523

Fri 2/105:30 p.m. -

1 stop7h 25m

Tue 6/109:05 p.m. -

2 stops14h 46m

Deal found 14/9C$ 524

Thu 1/105:30 p.m. -

1 stop7h 25m

Tue 6/109:05 p.m. -

2 stops14h 46m

Deal found 14/9C$ 526

Wed 28/106:20 p.m. -

2 stops23h 50m

Sun 1/115:00 a.m. -

1 stop12h 40m

Deal found 12/9C$ 533

Wed 30/911:45 a.m. -

1 stop20h 55m

Fri 2/105:10 p.m. -

1 stop17h 50m

Deal found 13/9C$ 542

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 17 September 2026.

Thu 1/103:20 p.m. -

1 stop17h 20m

Sat 3/104:25 p.m. -

1 stop18h 35m

Deal found 13/9C$ 510

Mon 28/98:03 a.m. -

1 stop7h 16m

Tue 29/99:20 a.m. -

1 stop6h 58m

Deal found 14/9C$ 886

Tue 6/105:30 p.m. -

1 stop7h 25m

Tue 13/106:00 a.m. -

2 stops15h 43m

Deal found 16/9C$ 986

Mon 19/108:55 a.m. -

1 stop7h 32m

Wed 21/1010:50 a.m. -

1 stop7h 51m

Deal found 15/9C$ 1,012

Wed 28/108:50 a.m. -

1 stop12h 07m

Wed 4/112:15 p.m. -

1 stop9h 09m

Deal found 13/9C$ 1,017

Fri 30/106:21 a.m. -

1 stop5h 27m

Fri 6/115:40 p.m. -

1 stop5h 41m

Deal found 15/9C$ 1,017

Thu 1/108:03 a.m. -

1 stop7h 17m

Mon 5/109:20 a.m. -

1 stop6h 54m

Deal found 17/9C$ 902

Thu 1/1012:17 p.m. -

1 stop12h 18m

Thu 5/112:10 p.m. -

3 stops27h 30m

Deal found 16/9C$ 919

Fri 13/115:30 p.m. -

2 stops22h 55m

Sat 21/115:32 p.m. -

1 stop5h 46m

Deal found 13/9C$ 1,015

Fri 13/118:50 a.m. -

1 stop12h 07m

Sat 21/112:15 p.m. -

1 stop9h 09m

Deal found 14/9C$ 1,017

Fri 13/116:13 a.m. -

1 stop5h 47m

Sat 21/115:32 p.m. -

1 stop5h 46m

Deal found 15/9C$ 1,070

Fri 6/1112:04 a.m. -

2 stops23h 26m

Tue 10/113:45 p.m. -

3 stops19h 55m

Deal found 13/9C$ 982

Fri 30/106:20 p.m. -

2 stops23h 50m

Fri 6/117:00 a.m. -

1 stop7h 37m

Deal found 15/9C$ 985

Thu 8/107:30 p.m. -

2 stops21h 45m

Fri 9/109:05 p.m. -

2 stops19h 53m

Deal found 12/9C$ 1,138

Wed 4/119:35 a.m. -

Nonstop2h 48m

Wed 11/112:15 p.m. -

Nonstop2h 35m

Deal found 12/9C$ 1,332

Wed 28/109:29 a.m. -

Nonstop2h 54m

Mon 2/112:15 p.m. -

Nonstop2h 35m

Deal found 17/9C$ 1,236

Thu 15/1011:45 a.m. -

2 stops30h 13m

Mon 19/104:15 p.m. -

2 stops22h 20m

Deal found 16/9C$ 1,198

Thu 1/108:55 a.m. -

2 stops8h 20m

Tue 6/106:15 a.m. -

2 stops14h 15m

Deal found 15/9C$ 1,208

Wed 4/111:27 p.m. -

2 stops9h 52m

Wed 11/116:35 a.m. -

1 stop5h 15m

Deal found 14/9C$ 1,421

Tue 8/129:35 a.m. -

Nonstop2h 48m

Sat 9/17:00 a.m. -

Nonstop2h 45m

Deal found 16/9C$ 1,371

Thu 1/109:29 a.m. -

2 stops7h 25m

Mon 5/1012:41 p.m. -

1 stop5h 38m

Deal found 15/9C$ 1,435

Thu 1/109:59 a.m. -

1 stop5h 09m

Mon 5/105:44 p.m. -

1 stop23h 03m

Deal found 17/9C$ 1,339

Sat 3/109:59 a.m. -

1 stop5h 09m

Wed 7/107:45 a.m. -

2 stops10h 15m

Deal found 15/9C$ 1,509

Fri 2/109:29 a.m. -

2 stops10h 11m

Tue 6/1012:38 p.m. -

1 stop4h 09m

Deal found 17/9C$ 1,445

Find flight deals from Illinois to Winnipeg

Round-trip from	C$ 441
One-way from	C$ 202
Popular in	August
Cheapest in	February
Average price	C$ 714

WestJet
15/10-19/10
2 total stops
17h 05m total
Illinois to Winnipeg

Search Deals

Porter Airlines
18/10-31/12
2 total stops
26h 38m total
Illinois to Winnipeg

Search Deals

Highest demand for flights based on searches. 16% potential increase in price (C$ 293 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 8% potential price decrease (C$ 122 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in September 2026

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

Fri 2/10

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

1 stop7h 25m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 219

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 26/10

3:30 p.m.-5:25 p.m.

2 stops25h 55m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 236

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$ 265

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 16/10

1:12 p.m.-5:25 p.m.

3 stops28h 13m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 304

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$ 312

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 27/11

2:28 p.m.-12:10 a.m.

2 stops33h 42m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 315

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 13/1

6:00 a.m.-2:40 p.m.

1 stop8h 40m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 317

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 1/10

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$ 319

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Sat 17/10

11:45 a.m.-2:15 p.m.

2 stops26h 30m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 321

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 1/10

7:45 p.m.-10:10 p.m.

2 stops26h 25m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 332

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/9

Showing 1-10 of 52 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, October is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 688). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,717). 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 (6 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$ 356 and C$ 1,602 in October.
The cheapest round-trip price found within the last 5 days was C$ 441 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 Porter Airlines, Air Canada, and WestJet fly from Illinois to Winnipeg in about 7h 16m. The time it takes to get you to your destination can typically vary by up to 15h 39m. 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 (67%), Air Canada (67%) and United Airlines (67%).
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$ 688). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,717). 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 round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 18/10. 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 17 September 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 17 September 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 17 September 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 17 September 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 17 September 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 17 September 2026.

Last-minute flights from Illinois to WinnipegDiscover last-minute flight deals from Illinois to Winnipeg. Data last updated 17 September 2026 and is based on user searches.

Discover last-minute flight deals from Illinois to Winnipeg. Data last updated 17 September 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 17 September 2026.

Search for one-way flight options from Illinois to Winnipeg. Find affordable one-way fares based on user searches. Data last updated 17 September 2026.

Find flight deals from Illinois to Winnipeg

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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 17 September 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 17 September 2026.

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 (6 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$ 356 and C$ 1,602 in October.The cheapest round-trip price found within the last 5 days was C$ 441 on WestJet (15 Oct-19 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?

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?

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Illinois and Winnipeg flights

Browse other Illinois and Winnipeg flight options. Last updated on 17 September 2026.

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

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

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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 17 September 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 17 September 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 17 September 2026.

Last-minute flights from Illinois to Winnipeg
Discover last-minute flight deals from Illinois to Winnipeg. Data last updated 17 September 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 17 September 2026.

Illinois to Winnipeg flights typically cost between C$ 356 and C$ 1,602 in October.
The cheapest round-trip price found within the last 5 days was C$ 441 on WestJet (15 Oct-19 Oct).