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Cheap flights from Illinois to Winnipeg from C$ 198

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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
5 May — 12 May1
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 30 April 2025.

Round-trip from

C$ 403

One-way from

C$ 198

Popular in

February

Cheapest in

January

Average price

C$ 1,028

Good round-trip deal

C$ 755 or less
WestJet
  • WestJet
  • 15/5-18/5
  • 2 total stops
  • 23h 47m total
  • Illinois to Winnipeg
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8/8
  • 8/8
  • 1 total stop
  • 10h 03m total
  • Illinois to Winnipeg
Search Deals
High demand for flights, 3% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Winnipeg.
Search Deals

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 30 April 2025.

Thu 15/55:30 p.m.ORD - YWG
1 stop15h 33mWestJet
Sun 18/58:30 a.m.YWG - ORD
1 stop8h 14mWestJet
Deal found 29/4C$ 403
Wed 25/65:01 a.m.ORD - YWG
1 stop11h 27mMultiple Airlines
Mon 30/69:00 a.m.YWG - ORD
1 stop5h 48mMultiple Airlines
Deal found 29/4C$ 411
Thu 15/59:50 a.m.STL - YWG
2 stops30h 05mMultiple Airlines
Mon 19/59:00 a.m.YWG - STL
2 stops9h 41mMultiple Airlines
Deal found 29/4C$ 581
Thu 5/66:30 a.m.MDW - YWG
1 stop9h 58mMultiple Airlines
Mon 9/69:00 a.m.YWG - MDW
1 stop9h 02mMultiple Airlines
Deal found 29/4C$ 633
Sun 15/67:58 p.m.ORD - YWG
Nonstop2h 35mAir Canada
Mon 16/67:00 a.m.YWG - ORD
Nonstop2h 31mAir Canada
Deal found 29/4C$ 664
Wed 10/92:00 p.m.MDW - YWG
1 stop6h 15mDelta
Sun 14/96:40 a.m.YWG - MDW
1 stop6h 29mDelta
Deal found 29/4C$ 685
Sat 31/57:10 a.m.ORD - YWG
2 stops9h 35mDelta
Tue 10/66:45 a.m.YWG - ORD
2 stops6h 10mDelta
Deal found 29/4C$ 706
Fri 13/69:21 a.m.MDW - YWG
1 stop14h 08mWestJet
Fri 20/69:00 a.m.YWG - MDW
1 stop12h 45mWestJet
Deal found 29/4C$ 727
Fri 6/67:58 p.m.ORD - YWG
Nonstop2h 35mUnited Airlines
Mon 9/62:20 p.m.YWG - ORD
Nonstop2h 31mUnited Airlines
Deal found 29/4C$ 765
Wed 10/99:15 a.m.MDW - YWG
2 stops11h 31mPorter Airlines
Sun 14/911:45 a.m.YWG - MDW
2 stops28h 39mPorter Airlines
Deal found 29/4C$ 789
Tue 10/67:00 a.m.STL - YWG
1 stop9h 28mDelta
Tue 17/69:00 a.m.YWG - STL
1 stop9h 44mDelta
Deal found 29/4C$ 833
Tue 27/58:15 a.m.STL - YWG
2 stops14h 18mUnited Airlines
Tue 3/61:40 p.m.YWG - STL
2 stops20h 16mUnited Airlines
Deal found 29/4C$ 974

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 30 April 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

Thu 15/5

5:30 p.m.-9:03 a.m.

1 stop15h 33m

Winnipeg

Sun 18/5

8:30 a.m.-4:44 p.m.

1 stop8h 14m

C$ 403

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 25/6

5:01 a.m.-4:28 p.m.

1 stop11h 27m

Winnipeg

Mon 30/6

9:00 a.m.-2:48 p.m.

1 stop5h 48m

C$ 411

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 15/5

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

2 stops30h 05m

Winnipeg

Mon 19/5

9:00 a.m.-6:41 p.m.

2 stops9h 41m

C$ 581

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 5/6

6:30 a.m.-4:28 p.m.

1 stop9h 58m

Winnipeg

Mon 9/6

9:00 a.m.-6:02 p.m.

1 stop9h 02m

C$ 633

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 15/6

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

Nonstop2h 35m

Winnipeg

Mon 16/6

7:00 a.m.-9:31 a.m.

Nonstop2h 31m

C$ 664

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 10/9

2:00 p.m.-8:15 p.m.

1 stop6h 15m

Winnipeg

Sun 14/9

6:40 a.m.-1:09 p.m.

1 stop6h 29m

C$ 685

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 31/5

7:10 a.m.-4:45 p.m.

2 stops9h 35m

Winnipeg

Tue 10/6

5:42 p.m.-9:37 p.m.

1 stop3h 55m

C$ 699

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 13/6

9:21 a.m.-11:29 p.m.

1 stop14h 08m

Winnipeg

Fri 20/6

9:00 a.m.-9:45 p.m.

1 stop12h 45m

C$ 727

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 6/6

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

Nonstop2h 35m

Winnipeg

Mon 9/6

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

Nonstop2h 31m

C$ 765

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 10/9

9:15 a.m.-8:46 p.m.

2 stops11h 31m

Winnipeg

Sun 14/9

11:45 a.m.-4:24 p.m.

2 stops28h 39m

C$ 789

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/4

Showing 1-10 of 23 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$ 124). Flying from Illinois to Winnipeg in July is currently the most expensive (average of C$ 232). 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 30 April 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 30 April 2025.

The most flights from USIL to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 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 30 April 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.
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,929 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,696 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,826 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,244 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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$ 274 on Porter Airlines. Other airlines that offer cheap prices include WestJet from C$ 275 and Air Canada from C$ 306 one-way.

  • 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 (89%), Air Canada (89%) and United Airlines (89%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 783 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 362 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 399.

  • 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$ 124). Flying from Illinois to Winnipeg in July is currently the most expensive (average of C$ 232). 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 30 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 443AverageC$ 1,004FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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