Winnipeg

$97+ Cheap flights from Illinois to Winnipeg (YWG)

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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Jan 22 — Jan 291
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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 January 17, 2025.

Round-trip from

$331
(Mytrip)

One-way from

$97
(Kiwi.com)
From Illinois to Winnipeg
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 January 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/66:15 amORD - YWG
1 stop10h 13mMultiple Airlines
Wed 5/79:00 amYWG - ORD
1 stop13h 21mMultiple Airlines
Deal found 1/16$273
This Kiwi.com deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/187:05 amMDW - YWG
1 stop8h 03mMultiple Airlines
Sun 4/207:30 amYWG - MDW
1 stop9h 31mMultiple Airlines
Deal found 1/16$323
This Justfly.com deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/55:30 pmORD - YWG
1 stop15h 31mWestJet
Sat 5/108:30 amYWG - ORD
1 stop8h 14mWestJet
Deal found 1/16$393
This Delta deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/65:50 amORD - YWG
1 stop10h 38mDelta
Fri 5/99:00 amYWG - ORD
1 stop12h 14mDelta
Deal found 1/16$533
This Air Canada deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/112:05 pmORD - YWG
1 stop6h 53mAir Canada
Thu 2/137:30 amYWG - ORD
1 stop5h 41mAir Canada
Deal found 1/16$534
This Gotogate deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/191:05 pmMDW - YWG
2 stops28h 59mPorter Airlines
Wed 2/2611:35 amYWG - MDW
2 stops24h 35mPorter Airlines
Deal found 1/15$540
This United Airlines deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/267:12 amORD - YWG
1 stop6h 46mUnited Airlines
Wed 3/264:30 pmYWG - ORD
1 stop7h 53mUnited Airlines
Deal found 1/16$561
This Delta deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/3012:44 pmMDW - YWG
2 stops23h 11mDelta
Wed 4/309:00 amYWG - MDW
1 stop13h 29mDelta
Deal found 1/16$572
This Priceline deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/1010:19 amMDW - YWG
1 stop6h 24mWestJet
Wed 2/125:00 amYWG - MDW
2 stops8h 05mWestJet
Deal found 1/16$644
This United Airlines deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/158:05 amSTL - YWG
1 stop7h 23mUnited Airlines
Fri 2/214:30 pmYWG - STL
2 stops26h 26mUnited Airlines
Deal found 1/15$789
This Justfly.com deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/206:30 amSTL - YWG
1 stop16h 52mWestJet
Sat 6/286:40 amYWG - STL
1 stop7h 36mWestJet
Deal found 1/15$801
This Air Canada deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/158:05 amSTL - YWG
1 stop7h 23mAir Canada
Fri 2/217:30 amYWG - STL
1 stop7h 36mAir Canada
Deal found 1/15$830

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 2,558,603 searches. Data last updated January 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/6

6:15 am-4:28 pm

1 stop10h 13m

Winnipeg

Wed 5/7

9:00 am-10:21 pm

1 stop13h 21m

$273

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/5

5:30 pm-9:01 am

1 stop15h 31m

Winnipeg

Sat 5/10

8:30 am-4:44 pm

1 stop8h 14m

$393

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 2/11

1:26 pm-10:45 am

2 stops21h 19m

Winnipeg

Thu 2/13

5:15 pm-12:10 pm

2 stops18h 55m

$506

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/6

5:50 am-4:28 pm

1 stop10h 38m

Winnipeg

Thu 5/8

9:00 am-12:06 am

1 stop15h 06m

$533

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 2/11

2:05 pm-8:58 pm

1 stop6h 53m

Winnipeg

Thu 2/13

7:30 am-1:11 pm

1 stop5h 41m

$534

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 2/19

1:05 pm-6:04 pm

2 stops28h 59m

Winnipeg

Wed 2/26

11:35 am-12:10 pm

2 stops24h 35m

$540

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 3/26

7:12 am-1:58 pm

1 stop6h 46m

Winnipeg

Wed 3/26

4:30 pm-12:23 am

1 stop7h 53m

$561

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 1/30

12:44 pm-11:55 am

2 stops23h 11m

Winnipeg

Wed 4/30

9:00 am-10:29 pm

1 stop13h 29m

$572

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 2/10

10:19 am-4:43 pm

1 stop6h 24m

Winnipeg

Wed 2/12

5:00 am-1:05 pm

2 stops8h 05m

$644

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 2/15

8:05 am-3:28 pm

1 stop7h 23m

Winnipeg

Fri 2/21

4:30 pm-6:56 pm

2 stops26h 26m

$789

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

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, August is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $358). Flying from Illinois to Winnipeg in February is currently the most expensive (average of $521). 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 January 17, 2025.

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

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 January 17, 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 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

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 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

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 January 17, 2025.
Read reviews from past customers who have flown United Airlines, Delta and Air Canada from Illinois to Winnipeg. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good
8,511 reviews

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

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

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

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

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

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

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

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

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

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

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

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?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Illinois. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

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

    $186 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Air Canada and United Airlines, with prices starting from $252 and $258, respectively.

  • What are the most popular routes from Illinois to Winnipeg?

  • What are the most reliable airlines from Illinois to Winnipeg?

    Consider SkyWest Airlines (79%), Air Canada (79%) or United Airlines (79%) when booking your flight. These represent the most reliable airlines when flying from Illinois to Winnipeg.

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay $424 for a flight from Illinois to Winnipeg. The cheapest flight overall is $118 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $262.

  • 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, August is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $358). Flying from Illinois to Winnipeg in February is currently the most expensive (average of $521). 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

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Alternative routes for Illinois to Winnipeg

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

Top 3 airlines flying from Illinois to Winnipeg

Discover the top 3 airlines 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 2,558,603 searches. Data last updated January 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$235Average$592FlexibilityNo cancel feeOn-time67%
DeltaCheapest$510Average$636FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$535Average$703FlexibilityNo cancel feeOn-time69%
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