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Cheap flights from Illinois to Winnipeg from C$ 152

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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
17 Jun — 24 Jun1
1 adult

Cheap flight deals from Illinois to Winnipeg

Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated 12 June 2025.

Round-trip from

C$ 353

One-way from

C$ 152

Popular in

February

Cheapest in

May

Average price

C$ 774

Good one-way deal

C$ 344 or less
8/7-11/7
  • 8/7-11/7
  • 3 total stops
  • 26h 18m total
  • Illinois to Winnipeg
8/7
  • 8/7
  • 2 total stops
  • 13h 48m total
  • Illinois to Winnipeg
Highest demand for flights based on searches. 2% potential increase in price (C$ 22 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease (C$ 38 potential savings vs. average RT price).
Average for round-trip flights in June 2025
Price to beat on a one-way flight from Illinois to Winnipeg.

Find flight deals from Illinois to Winnipeg

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 12 June 2025.

Tue 8/710:43 a.m.ORD - YWG
2 stops13h 48mMultiple Airlines
Fri 11/79:00 a.m.YWG - ORD
1 stop12h 30mMultiple Airlines
Deal found 10/6C$ 353
Fri 17/105:30 p.m.ORD - YWG
1 stop28h 00mWestJet
Mon 20/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 12/6C$ 392
Mon 22/96:15 a.m.MDW - YWG
1 stop10h 07mMultiple Airlines
Thu 25/99:00 a.m.YWG - MDW
1 stop9h 18mMultiple Airlines
Deal found 11/6C$ 429
Mon 22/99:30 a.m.MDW - YWG
2 stops14h 02mDelta
Tue 30/96:40 a.m.YWG - MDW
2 stops15h 04mDelta
Deal found 11/6C$ 552
Wed 24/97:00 a.m.ORD - YWG
2 stops13h 15mDelta
Tue 30/96:40 a.m.YWG - ORD
2 stops17h 13mDelta
Deal found 11/6C$ 632
Thu 3/79:50 a.m.STL - YWG
2 stops30h 05mMultiple Airlines
Mon 7/78:55 p.m.YWG - STL
3 stops37h 34mMultiple Airlines
Deal found 11/6C$ 680
Tue 28/109:50 a.m.ORD - YWG
1 stop6h 08mAir Canada
Fri 7/115:15 a.m.YWG - ORD
1 stop5h 43mAir Canada
Deal found 11/6C$ 701
Fri 18/79:40 a.m.MDW - YWG
2 stops13h 06mPorter Airlines
Sun 20/76:55 p.m.YWG - MDW
1 stop13h 50mPorter Airlines
Deal found 11/6C$ 742
Tue 28/109:20 a.m.MDW - YWG
2 stops10h 15mWestJet
Fri 7/115:00 a.m.YWG - MDW
2 stops16h 44mWestJet
Deal found 12/6C$ 815
Thu 7/81:30 p.m.STL - YWG
1 stop6h 59mAir Canada
Sun 10/87:40 a.m.YWG - STL
1 stop7h 41mAir Canada
Deal found 11/6C$ 942
Thu 3/78:00 a.m.STL - YWG
1 stop7h 31mUnited Airlines
Mon 7/77:00 a.m.YWG - STL
1 stop5h 27mUnited Airlines
Deal found 11/6C$ 953
Thu 31/711:18 a.m.STL - YWG
1 stop8h 52mDelta
Sat 9/86:45 a.m.YWG - STL
2 stops7h 51mDelta
Deal found 11/6C$ 965

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 12 June 2025.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Illinois

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 8/7

10:43 a.m.-12:31 a.m.

2 stops13h 48m

Winnipeg

Fri 11/7

9:00 a.m.-9:30 p.m.

1 stop12h 30m

C$ 353

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/9

5:30 p.m.-11:41 a.m.

1 stop18h 11m

Winnipeg

Wed 10/9

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 406

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 18/7

6:20 a.m.-4:23 p.m.

1 stop10h 03m

Winnipeg

Sun 20/7

6:30 a.m.-4:24 p.m.

1 stop9h 54m

C$ 640

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 3/7

9:50 a.m.-3:55 p.m.

2 stops30h 05m

Winnipeg

Mon 7/7

8:55 p.m.-10:29 a.m.

3 stops37h 34m

C$ 680

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 26/7

7:58 p.m.-10:33 p.m.

Nonstop2h 35m

Winnipeg

Sat 2/8

6:35 p.m.-9:09 a.m.

1 stop14h 34m

C$ 715

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 18/7

9:40 a.m.-10:46 p.m.

2 stops13h 06m

Winnipeg

Sun 20/7

6:55 p.m.-8:45 a.m.

1 stop13h 50m

C$ 742

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 20/7

7:58 p.m.-10:33 p.m.

Nonstop2h 35m

Winnipeg

Mon 28/7

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

C$ 756

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 4/7

11:00 a.m.-11:29 p.m.

2 stops12h 29m

Winnipeg

Fri 11/7

5:42 p.m.-9:34 p.m.

1 stop3h 52m

C$ 760

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 5/7

6:00 a.m.-11:29 p.m.

2 stops17h 29m

Winnipeg

Fri 11/7

8:35 a.m.-5:39 p.m.

1 stop9h 04m

C$ 763

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 8/7

7:21 p.m.-11:31 a.m.

1 stop16h 10m

Winnipeg

Fri 11/7

9:00 a.m.-9:42 p.m.

1 stop12h 42m

C$ 844

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 22 results
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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 month to book a flight from Illinois to Winnipeg?

Currently, January is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 123). Flying from Illinois to Winnipeg in July is currently the most expensive (average of C$ 229). 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?

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 12 June 2025.

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 12 June 2025.

The most flights from USIL to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

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.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

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).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated 12 June 2025.
See what other customers who have flown with Porter Airlines, Delta and United Airlines from Illinois to Winnipeg have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

7.6

Boarding

8.2

Comfort

8.1

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Food

7.6

Boarding

8.2

Comfort

8.1

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
8.0
Very good

Food

7.6

Boarding

8.2

Comfort

8.1

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Food

7.6

Boarding

8.2

Comfort

8.1

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Food

7.6

Boarding

8.2

Comfort

8.1

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Food

7.6

Boarding

8.2

Comfort

8.1

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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.

  • What are the cheapest airlines to fly from Illinois to Winnipeg one-way?

    One-way options have recently been found by users for as low as C$ 186 on WestJet. Other airlines that offer cheap prices include Porter Airlines from C$ 297 and United Airlines from C$ 345 one-way.

  • What are the most popular routes from Illinois to 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 (78%), Air Canada (78%) and United Airlines (78%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 344 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 231 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 338.

  • 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, January is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 123). Flying from Illinois to Winnipeg in July is currently the most expensive (average of C$ 229). 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

Travelling to a place near Illinois?

Book flights to Illinois if you plan to visit one of these locations
Selkirk
Portage la Prairie

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Top airline flying from Illinois to Winnipeg

Discover the top airline that operate flights from Illinois to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 438AverageC$ 991FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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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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