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$192+ Cheap flights from Cleveland (CLE) 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — YWG
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Cleveland to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Cleveland (CLE) 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 August 14, 2025.

Round-trip from

$307
(Kiwi.com)

One-way from

$192
(Trip.com)

Popular in

November

Cheapest in

January

Average price

$771
From Cleveland Hopkins Intl to Winnipeg
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One-way flight from Cleveland Hopkins Intl to Winnipeg
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Highest demand for flights based on searches. 2% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Cleveland to Winnipeg

Cheapest flights from Cleveland to Winnipeg
Explore the most affordable flight options available from Cleveland to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Sun 9/212:11 pmCLE - YWG
1 stop26h 44mMultiple Airlines
Thu 9/259:00 amYWG - CLE
1 stop14h 43mMultiple Airlines
Deal found 8/13$307
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/195:30 amCLE - YWG
1 stop11h 52mMultiple Airlines
Mon 9/229:05 pmYWG - CLE
2 stops14h 30mMultiple Airlines
Deal found 8/13$335
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Thu 8/215:30 amCLE - YWG
1 stop11h 53mMultiple Airlines
Fri 8/299:00 amYWG - CLE
1 stop23h 11mMultiple Airlines
Deal found 8/13$381
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/55:30 amCLE - YWG
1 stop11h 52mMultiple Airlines
Sun 9/77:00 pmYWG - CLE
2 stops23h 06mMultiple Airlines
Deal found 8/14$453

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cleveland 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 August 14, 2025.
Use the filters below to find and compare flights from Cleveland to Winnipeg that are best for you.

Fly from

Cleveland

Fly to

Winnipeg

Route

Depart

Return

Price

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Sun 9/21

2:11 pm-3:55 pm

1 stop26h 44m

Winnipeg

Thu 9/25

9:00 am-12:43 am

1 stop14h 43m

$307

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 9/19

5:30 am-4:22 pm

1 stop11h 52m

Winnipeg

Mon 9/22

9:05 pm-12:35 pm

2 stops14h 30m

$335

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 9/5

5:30 am-4:22 pm

1 stop11h 52m

Winnipeg

Sun 9/7

7:00 pm-7:06 pm

2 stops23h 06m

$453

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 9/5

7:35 pm-10:33 pm

1 stop27h 58m

Winnipeg

Sun 9/7

7:00 am-9:49 am

1 stop25h 49m

$731

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Thu 8/21

5:30 am-4:23 pm

1 stop11h 53m

$192

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Wed 8/20

5:31 pm-4:23 pm

2 stops23h 52m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Best time to book a flight from Cleveland to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Cleveland 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 Cleveland to Winnipeg

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

Currently, August is the cheapest month in which you can book a flight from Cleveland to Winnipeg (average of $358). Flying from Cleveland to Winnipeg in December is currently the most expensive (average of $495). 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 CLE to YWG?

Find hourly flight availability from Cleveland 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 August 14, 2025.

It’s optimal to fly from Cleveland to Winnipeg in the morning. By choosing this option you can save up to 13% on the cost of your flight, compared to a flight in the afternoon.

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 August 14, 2025.
Get a feel of what it's like to fly with Delta and United Airlines from Cleveland to Winnipeg by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,916 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Cleveland to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Cleveland to Winnipeg round-trip?

    According to our current data, Delta ($585), and United Airlines ($638) offers the cheapest pricing from Cleveland to Winnipeg. You may be able to fly from Cleveland to Winnipeg for 27% less than the average price by searching for these airlines.

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

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

  • How can I find direct flights from Cleveland to Winnipeg?

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

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

    Yes. Cheapflights offers flight deals from Cleveland 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 Cleveland to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Cleveland to Winnipeg (average of $358). Flying from Cleveland to Winnipeg in December is currently the most expensive (average of $495). 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

Traveling to a place near Winnipeg?

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

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Alternative routes for Cleveland to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Cleveland to Winnipeg

Discover the top 2 airlines that operate flights from Cleveland 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$585Average$753FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$638Average$806FlexibilityNo cancel feeOn-time69%

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