How long is the flight from Winnipeg to Illinois?

Departing from Winnipeg to Illinois will take you 8h 42m. The distance between Winnipeg and Illinois is about 1136 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

In terms of precipitation, rainfall in Illinois ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Illinois when rainfall is around 43.0 mm.

If weather is an important factor for your trip to Illinois, 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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

What are the cheapest flights from Winnipeg to Illinois?

While on average a flight from Winnipeg to Illinois is generally C$ 884, our data shows the cheapest flight currently is C$ 432. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 528 for that flight.

What are the most reliable airlines from Winnipeg to Illinois?

Consider Copa Airlines (95%), Air Canada (87%) or Air New Zealand (87%) when booking your flight. These represent the most reliable airlines when flying from Winnipeg to Illinois.

What are the most popular airlines that fly from Winnipeg to Illinois?

Before booking your flight from Winnipeg to Illinois check out the most popular airlines for this route: Air Canada, United Airlines or WestJet.

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

If you book a flight to Illinois from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg.

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

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

How can I find direct flights from Winnipeg to Illinois?

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

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

Yes. Cheapflights offers flight deals from Winnipeg to Illinois 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$ 277+ Cheap Flights from Winnipeg to Illinois

Cheap flight deals from Winnipeg to Illinois

Enter your travel dates to find the best prices.

Cheapest

Best

Direct

Last-minute

One-way

Cheapest flights from Winnipeg to Illinois
Explore the most affordable flight options available from Winnipeg to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 15 November 2026.

Mon 14/129:35 p.m. -

2 stops17h 55m

Mon 21/125:58 a.m. -

1 stop7h 42m

Deal found 14/11C$ 555

Mon 7/129:35 p.m. -

2 stops17h 55m

Wed 9/128:30 a.m. -

2 stops15h 40m

Deal found 12/11C$ 588

Mon 7/129:35 p.m. -

2 stops17h 55m

Thu 10/1210:29 p.m. -

2 stops17h 56m

Deal found 12/11C$ 602

Mon 7/129:35 p.m. -

2 stops14h 58m

Thu 10/125:02 p.m. -

2 stops23h 23m

Deal found 12/11C$ 625

Mon 7/129:35 p.m. -

2 stops20h 31m

Thu 10/126:20 a.m. -

1 stop4h 11m

Deal found 15/11C$ 634

Mon 7/125:45 p.m. -

1 stop22h 08m

Wed 9/1210:36 a.m. -

2 stops13h 34m

Deal found 12/11C$ 635

Sun 6/129:35 p.m. -

2 stops19h 31m

Thu 10/125:02 p.m. -

2 stops23h 23m

Deal found 12/11C$ 649

Tue 1/1212:10 p.m. -

2 stops34h 25m

Sat 5/128:30 a.m. -

2 stops25h 50m

Deal found 13/11C$ 652

Tue 15/129:35 p.m. -

2 stops17h 55m

Tue 22/125:58 a.m. -

2 stops18h 12m

Deal found 14/11C$ 653

Thu 3/129:35 p.m. -

2 stops21h 28m

Sun 6/128:30 a.m. -

2 stops15h 40m

Deal found 13/11C$ 656

Thu 10/129:35 p.m. -

2 stops19h 31m

Sun 13/128:37 p.m. -

3 stops27h 33m

Deal found 10/11C$ 678

Mon 14/127:00 a.m. -

1 stop28h 28m

Tue 15/1212:39 p.m. -

1 stop11h 00m

Deal found 14/11C$ 759

Best flights from Winnipeg to Illinois
Discover carefully curated flight deals from Winnipeg to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 15 November 2026.

Thu 26/1110:00 a.m. -

2 stops25h 01m

Wed 9/126:20 p.m. -

1 stop14h 55m

Deal found 10/11C$ 669

Thu 25/29:35 p.m. -

2 stops13h 30m

Sun 28/210:50 a.m. -

2 stops29h 35m

Deal found 14/11C$ 709

Mon 14/127:00 a.m. -

1 stop8h 42m

Wed 16/129:42 a.m. -

1 stop25h 05m

Deal found 14/11C$ 820

Mon 18/18:00 a.m. -

Nonstop2h 45m

Thu 21/13:50 p.m. -

Nonstop2h 38m

Deal found 13/11C$ 953

Sat 1/56:35 a.m. -

2 stops9h 50m

Sat 8/59:55 a.m. -

1 stop5h 05m

Deal found 13/11C$ 962

Thu 10/129:35 p.m. -

2 stops19h 31m

Sun 13/128:37 p.m. -

3 stops27h 33m

Deal found 10/11C$ 678

Mon 15/27:00 a.m. -

1 stop10h 36m

Fri 19/21:18 p.m. -

2 stops34h 52m

Deal found 13/11C$ 685

Thu 25/29:35 p.m. -

2 stops22h 12m

Sun 28/29:55 a.m. -

2 stops14h 49m

Deal found 10/11C$ 905

Sun 27/127:00 a.m. -

1 stop7h 15m

Sun 3/16:50 p.m. -

1 stop27h 09m

Deal found 12/11C$ 909

Wed 16/123:15 p.m. -

Nonstop2h 45m

Mon 21/1210:00 a.m. -

Nonstop2h 52m

Deal found 13/11C$ 953

Tue 8/126:25 a.m. -

1 stop11h 25m

Wed 9/129:37 a.m. -

2 stops25h 28m

Deal found 12/11C$ 945

Mon 15/28:00 a.m. -

Nonstop2h 31m

Fri 19/210:51 a.m. -

1 stop10h 06m

Deal found 13/11C$ 953

Thu 17/126:25 a.m. -

2 stops12h 36m

Mon 21/126:00 a.m. -

1 stop7h 40m

Deal found 14/11C$ 1,087

Sun 27/127:00 a.m. -

3 stops18h 15m

Sun 3/15:00 a.m. -

3 stops18h 24m

Deal found 12/11C$ 2,199

Sat 1/52:15 p.m. -

Nonstop2h 21m

Sat 8/510:50 a.m. -

1 stop10h 07m

Deal found 13/11C$ 953

Fri 25/127:00 a.m. -

1 stop8h 41m

Wed 30/126:00 a.m. -

1 stop7h 40m

Deal found 12/11C$ 1,100

Fri 19/37:00 a.m. -

Nonstop2h 31m

Mon 22/33:50 p.m. -

Nonstop2h 51m

Deal found 10/11C$ 963

Mon 14/127:00 a.m. -

1 stop28h 28m

Mon 21/129:58 a.m. -

2 stops14h 12m

Deal found 14/11C$ 1,097

Thu 26/119:35 p.m. -

2 stops15h 59m

Sat 28/1112:30 p.m. -

1 stop11h 03m

Deal found 12/11C$ 1,103

Tue 8/126:25 a.m. -

1 stop6h 34m

Wed 9/1212:39 p.m. -

1 stop21h 52m

Deal found 12/11C$ 1,126

Mon 14/123:15 p.m. -

Nonstop2h 45m

Mon 21/1210:00 a.m. -

Nonstop2h 52m

Deal found 14/11C$ 975

Thu 17/123:15 p.m. -

Nonstop2h 47m

Mon 21/1210:00 a.m. -

Nonstop2h 52m

Deal found 14/11C$ 980

Sun 27/128:20 p.m. -

2 stops27h 22m

Sun 3/16:15 a.m. -

1 stop6h 37m

Deal found 12/11C$ 1,193

Find flight deals from Winnipeg to Illinois

Round-trip from	C$ 528
One-way from	C$ 271
Popular in	June
Cheapest in	February
Average price	C$ 800
Good round-trip deal	C$ 884 or less
Good one-way deal	C$ 539 or less

18/1-21/1
3 total stops
44h 34m total
Winnipeg to Illinois

Search Deals

15/12-31/12
2 total stops
25h 25m total
Winnipeg to Illinois

Search Deals

Highest demand for flights based on searches. 6% potential increase in price (C$ 93 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease (C$ 40 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in November 2026

Search Deals

Price to beat on a round-trip flight from Winnipeg to Illinois.

Search Deals

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

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 1/12

9:35 p.m.-3:00 p.m.

2 stops17h 25m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 298

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Wed 23/12

7:00 a.m.-1:01 a.m.

1 stop18h 01m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 331

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Tue 15/12

9:35 p.m.-5:16 p.m.

2 stops19h 41m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 344

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Tue 1/12

9:35 p.m.-12:33 p.m.

2 stops14h 58m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 345

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Thu 3/12

9:35 p.m.-5:16 p.m.

2 stops19h 41m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 364

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 11/12

7:00 a.m.-2:01 p.m.

1 stop7h 01m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 367

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 4/12

9:35 p.m.-12:33 p.m.

2 stops14h 58m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 382

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 28/12

4:00 p.m.-6:49 a.m.

1 stop14h 49m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 404

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 4/12

9:35 p.m.-12:34 p.m.

2 stops14h 59m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 412

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Wed 16/12

6:00 a.m.-7:01 p.m.

2 stops13h 01m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 467

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 44 resultsSorted by cheapest first

...

Best time to book a flight from Winnipeg to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Winnipeg with our price prediction graph.

YWG-ORD

YWG-MDW

YWG-PIA

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 Winnipeg to Illinois

YWG-USIL

YWG-ORD

YWG-MDW

YWG-PIA

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

Currently, May is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 773). Flying from Winnipeg to Illinois in October is currently the most expensive (average of C$ 1,077). 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 YWG to IL?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Illinois as you normally would.

Weekly flight availability from Winnipeg to Illinois

The most flights from YWG to USIL are scheduled on a Tuesday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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

Airfare is below average for this route at the moment.

Winnipeg to Illinois flights typically cost between C$ 853 and C$ 1,017 in January.
The cheapest round-trip price found within the last 5 days was C$ 528 on Multiple Airlines (18 Jan-21 Jan).

Reviews of airlines servicing Illinois

See what other customers who have flown with United Airlines,WestJet, andAir Canada from Winnipeg to Illinois have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

United Airlines

7.3

Good

10,492 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!

United Airlines

7.3

Good

10,492 reviews

United Airlines

7.3

Good

10,492 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Chris,Aug 2026

MIA - ORD

WestJet

7.2

Good

3,436 reviews

United Airlines

7.3

Good

10,492 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Chris,Aug 2026

MIA - ORD

Air Canada

7.1

Good

11,898 reviews

United Airlines

7.3

Good

10,492 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Chris,Aug 2026

MIA - ORD

Related info for your journey

What airport do you fly from for flights from Winnipeg to Illinois?
If you book a flight to Illinois from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg.
How long is the flight from Winnipeg to Illinois?
Departing from Winnipeg to Illinois will take you 8h 42m. The distance between Winnipeg and Illinois is about 1136 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.
What are the most reliable airlines from Winnipeg to Illinois?
Consider Copa Airlines (95%), Air Canada (87%) or Air New Zealand (87%) when booking your flight. These represent the most reliable airlines when flying from Winnipeg to Illinois.
What are the cheapest flights from Winnipeg to Illinois?
While on average a flight from Winnipeg to Illinois is generally C$ 884, our data shows the cheapest flight currently is C$ 432. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 528 for that flight.
Can I find deals for flights from Winnipeg to Illinois that include hotel bookings?
Yes. In addition to deals on Winnipeg to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Winnipeg to Illinois?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Illinois.
Can I find deals for business class flights from Winnipeg to Illinois?
Yes. Cheapflights offers flight deals from Winnipeg to Illinois 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 Winnipeg to Illinois?
Currently, May is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 773). Flying from Winnipeg to Illinois in October is currently the most expensive (average of C$ 1,077). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes

Complete your trip

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Top 3 airlines flying from Winnipeg to Illinois

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 279	AverageC$ 544	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
United Airlines	CheapestC$ 708	AverageC$ 988	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights
Air Canada	CheapestC$ 726	AverageC$ 907	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights

Fly with Cheapflights

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

Cheapflights helps you search for flights from Winnipeg to Illinois via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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

Cheapflights helps you find that perfect flight to Illinois from Winnipeg by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

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

Certainly. Search results for flights to Illinois from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

Of course! You can now track prices for flights from Winnipeg to Illinois and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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Cheap flights from Winnipeg to Illinois from C$ 277

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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Winnipeg to Illinois

Cheapest flights from Winnipeg to IllinoisExplore the most affordable flight options available from Winnipeg to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 15 November 2026.

Explore the most affordable flight options available from Winnipeg to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 15 November 2026.

Best flights from Winnipeg to IllinoisDiscover carefully curated flight deals from Winnipeg to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 15 November 2026.

Discover carefully curated flight deals from Winnipeg to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 15 November 2026.

Direct flights from Winnipeg to IllinoisExplore direct flight options from Winnipeg to Illinois based on user searches, and compare prices and availability for your desired travel dates. Data last updated 15 November 2026.

Explore direct flight options from Winnipeg to Illinois based on user searches, and compare prices and availability for your desired travel dates. Data last updated 15 November 2026.

Last-minute flights from Winnipeg to IllinoisDiscover last-minute flight deals from Winnipeg to Illinois. Data last updated 15 November 2026 and is based on user searches.

Discover last-minute flight deals from Winnipeg to Illinois. Data last updated 15 November 2026 and is based on user searches.

One-way flights from Winnipeg to IllinoisSearch for one-way flight options from Winnipeg to Illinois. Find affordable one-way fares based on user searches. Data last updated 15 November 2026.

Search for one-way flight options from Winnipeg to Illinois. Find affordable one-way fares based on user searches. Data last updated 15 November 2026.

Find flight deals from Winnipeg to Illinois

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Cheapflights Fare Finder

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

Best time to book a flight from Winnipeg to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Winnipeg with our price prediction graph.

Cheapflights Insights

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

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

Find hourly flight availability from Winnipeg to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 15 November 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Illinois as you normally would.

Weekly flight availability from Winnipeg to Illinois

Explore weekly flight availability from Winnipeg to Illinois. 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 15 November 2026.

The most flights from YWG to USIL are scheduled on a Tuesday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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

Airfare is below average for this route at the moment.

Winnipeg to Illinois flights typically cost between C$ 853 and C$ 1,017 in January.The cheapest round-trip price found within the last 5 days was C$ 528 on Multiple Airlines (18 Jan-21 Jan).

Reviews of airlines servicing Illinois

See what other customers who have flown with United Airlines,WestJet, andAir Canada from Winnipeg to Illinois have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

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

How long is the flight from Winnipeg to Illinois?

What are the most reliable airlines from Winnipeg to Illinois?

What are the cheapest flights from Winnipeg to Illinois?

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

How can I find direct flights from Winnipeg to Illinois?

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Illinois

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.

Direct flights to United States

Book a non-stop flight to one of these other cities located in United States.

Search flights from Winnipeg to Illinois by cabin class

Find flights from Winnipeg to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Winnipeg and Illinois flights

Browse other Winnipeg and Illinois flight options. Last updated on 15 November 2026.

Popular flight searches

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Top 3 airlines flying from Winnipeg to Illinois

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

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

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

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

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Cheapest flights from Winnipeg to Illinois
Explore the most affordable flight options available from Winnipeg to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 15 November 2026.

Best flights from Winnipeg to Illinois
Discover carefully curated flight deals from Winnipeg to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 15 November 2026.

Direct flights from Winnipeg to Illinois
Explore direct flight options from Winnipeg to Illinois based on user searches, and compare prices and availability for your desired travel dates. Data last updated 15 November 2026.

Last-minute flights from Winnipeg to Illinois
Discover last-minute flight deals from Winnipeg to Illinois. Data last updated 15 November 2026 and is based on user searches.

One-way flights from Winnipeg to Illinois
Search for one-way flight options from Winnipeg to Illinois. Find affordable one-way fares based on user searches. Data last updated 15 November 2026.

Winnipeg to Illinois flights typically cost between C$ 853 and C$ 1,017 in January.
The cheapest round-trip price found within the last 5 days was C$ 528 on Multiple Airlines (18 Jan-21 Jan).