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Cheap flights from Illinois to Winnipeg from C$ 139

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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
22 Jan — 29 Jan1
1 adult

Cheap flight deals from Illinois to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 17 January 2025.

Round-trip from

C$ 392

One-way from

C$ 139
6/5-7/5
  • 6/5-7/5
  • 2 total stops
  • 23h 34m total
  • Illinois to Winnipeg
1/4
  • 1/4
  • 1 total stop
  • 21h 12m total
  • 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 17 January 2025.

Tue 6/56:15 a.m.ORD - YWG
1 stop10h 13mMultiple Airlines
Wed 7/59:00 a.m.YWG - ORD
1 stop13h 21mMultiple Airlines
Deal found 16/1C$ 392
Fri 18/47:05 a.m.MDW - YWG
1 stop8h 03mMultiple Airlines
Sun 20/47:30 a.m.YWG - MDW
1 stop9h 31mMultiple Airlines
Deal found 16/1C$ 464
Mon 5/55:30 p.m.ORD - YWG
1 stop15h 31mWestJet
Sat 10/58:30 a.m.YWG - ORD
1 stop8h 14mWestJet
Deal found 16/1C$ 565
Tue 6/55:50 a.m.ORD - YWG
1 stop10h 38mDelta
Thu 8/59:00 a.m.YWG - ORD
1 stop15h 06mDelta
Deal found 16/1C$ 766
Tue 11/22:05 p.m.ORD - YWG
1 stop6h 53mAir Canada
Thu 13/27:30 a.m.YWG - ORD
1 stop5h 41mAir Canada
Deal found 16/1C$ 767
Wed 19/21:05 p.m.MDW - YWG
2 stops28h 59mPorter Airlines
Wed 26/211:35 a.m.YWG - MDW
2 stops24h 35mPorter Airlines
Deal found 15/1C$ 776
Wed 26/37:12 a.m.ORD - YWG
1 stop6h 46mUnited Airlines
Wed 26/34:30 p.m.YWG - ORD
1 stop7h 53mUnited Airlines
Deal found 16/1C$ 806
Sun 16/24:00 p.m.STL - YWG
3 stops32h 32mMultiple Airlines
Sat 22/28:15 p.m.YWG - STL
2 stops18h 27mMultiple Airlines
Deal found 16/1C$ 812
Thu 30/112:44 p.m.MDW - YWG
2 stops23h 11mDelta
Wed 30/49:00 a.m.YWG - MDW
1 stop13h 29mDelta
Deal found 16/1C$ 822
Mon 10/210:19 a.m.MDW - YWG
1 stop6h 24mWestJet
Wed 12/25:00 a.m.YWG - MDW
2 stops8h 05mWestJet
Deal found 16/1C$ 926
Sun 16/26:00 a.m.STL - YWG
1 stop5h 51mDelta
Sat 22/26:40 a.m.YWG - STL
1 stop8h 10mDelta
Deal found 16/1C$ 1,107
Sun 16/28:20 a.m.STL - YWG
2 stops12h 50mAir Canada
Sat 22/27:15 a.m.YWG - STL
2 stops9h 51mAir Canada
Deal found 16/1C$ 1,214

Find flights from Illinois to Winnipeg within your budget

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 17 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 6/5

6:15 a.m.-4:28 p.m.

1 stop10h 13m

Winnipeg

Wed 7/5

9:00 a.m.-10:21 p.m.

1 stop13h 21m

C$ 392

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 18/4

7:05 a.m.-3:08 p.m.

1 stop8h 03m

Winnipeg

Sun 20/4

7:30 a.m.-5:01 p.m.

1 stop9h 31m

C$ 464

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/5

5:30 p.m.-9:01 a.m.

1 stop15h 31m

Winnipeg

Sat 10/5

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

1 stop8h 14m

C$ 565

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 6/5

5:50 a.m.-4:28 p.m.

1 stop10h 38m

Winnipeg

Thu 8/5

9:00 a.m.-12:06 a.m.

1 stop15h 06m

C$ 766

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 11/2

2:05 p.m.-8:58 p.m.

1 stop6h 53m

Winnipeg

Thu 13/2

7:30 a.m.-1:11 p.m.

1 stop5h 41m

C$ 767

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 19/2

1:05 p.m.-6:04 p.m.

2 stops28h 59m

Winnipeg

Wed 26/2

11:35 a.m.-12:10 p.m.

2 stops24h 35m

C$ 776

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 26/3

7:12 a.m.-1:58 p.m.

1 stop6h 46m

Winnipeg

Wed 26/3

4:30 p.m.-12:23 a.m.

1 stop7h 53m

C$ 806

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 16/2

4:00 p.m.-12:32 a.m.

3 stops32h 32m

Winnipeg

Sat 22/2

8:15 p.m.-2:42 p.m.

2 stops18h 27m

C$ 812

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 30/1

12:44 p.m.-11:55 a.m.

2 stops23h 11m

Winnipeg

Wed 30/4

9:00 a.m.-10:29 p.m.

1 stop13h 29m

C$ 822

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 10/2

10:19 a.m.-4:43 p.m.

1 stop6h 24m

Winnipeg

Wed 12/2

5:00 a.m.-1:05 p.m.

2 stops8h 05m

C$ 926

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/1

Showing 1-10 of 21 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.

Travel insights for flights from Illinois to Winnipeg

Get recent, data-driven insights about flights from Illinois to Winnipeg including ideal travel times, pricing trends, and more.

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$ 130). Flying from Illinois to Winnipeg in March is currently the most expensive (average of C$ 240). 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 17 January 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 17 January 2025.

The most flights from USIL to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, 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 17 January 2025.
See what other customers who have flown with WestJet, Delta and Air Canada 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.
8.0
Very good
8,511 reviews

Food

7.3

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

8.0
Very good
8,511 reviews
8.0
Very good
8,511 reviews

Food

7.3

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

7.9
Good
276 reviews
8.0
Very good
8,511 reviews

Food

7.3

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

7.4
Good
8,965 reviews
8.0
Very good
8,511 reviews

Food

7.3

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

7.2
Good
2,824 reviews
8.0
Very good
8,511 reviews

Food

7.3

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

7.0
Good
8,587 reviews
8.0
Very good
8,511 reviews

Food

7.3

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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$ 267 on Delta. Other airlines that offer cheap prices include Air Canada from C$ 362 and United Airlines from C$ 371 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 (79%), Air Canada (79%) and United Airlines (79%).

  • 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$ 130). Flying from Illinois to Winnipeg in March is currently the most expensive (average of C$ 240). 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
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 17 January 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 507AverageC$ 992FlexibilityNo 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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