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$244+ Cheap flights from Cleveland (CLE) to Winnipeg (YWG)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — YWG
dic. 26 — ene. 21
vie. 12/26
vie. 1/2
1 adult, Economy
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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 noviembre 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
mar. 12/21:41 pmCLE - YWG
1 stop26h 26mMultiple Airlines
dom. 12/77:30 amYWG - CLE
1 stop14h 38mMultiple Airlines
Deal found 11/25$244
This Kiwi.com deal was found by Cheapflights users on 11/26. 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.
vie. 12/57:14 amCLE - YWG
1 stop8h 53mMultiple Airlines
dom. 12/77:30 amYWG - CLE
1 stop8h 48mMultiple Airlines
Deal found 11/26$248
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
mar. 12/21:41 pmCLE - YWG
1 stop26h 26mMultiple Airlines
lun. 12/89:00 pmYWG - CLE
2 stops14h 11mMultiple Airlines
Deal found 11/25$249
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
jue. 12/45:33 pmCLE - YWG
1 stop22h 34mMultiple Airlines
dom. 12/77:30 amYWG - CLE
1 stop14h 38mMultiple Airlines
Deal found 11/25$255
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
jue. 12/45:33 pmCLE - YWG
1 stop22h 34mMultiple Airlines
lun. 12/89:00 pmYWG - CLE
2 stops14h 11mMultiple Airlines
Deal found 11/25$257

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 noviembre 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$248
(Kiwi.com)

Popular in

November

Cheapest in

December

Average price

$1,064
Provider with most accurate pricing for Cleveland Hopkins Intl-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Winnipeg flights.
Search Deals
From Cleveland Hopkins Intl to Winnipeg
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 noviembre 26, 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

mar. 12/2

1:41 pm-3:07 pm

1 stop26h 26m

Winnipeg

lun. 12/8

8:00 am-10:02 pm

2 stops37h 02m

$292

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

mié. 12/3

1:41 pm-12:39 am

2 stops35h 58m

Winnipeg

lun. 12/8

8:00 am-10:13 pm

1 stop13h 13m

$488

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

mar. 12/2

6:05 am-12:42 am

2 stops19h 37m

Winnipeg

lun. 12/8

12:20 pm-9:21 am

2 stops20h 01m

$732

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

mié. 12/3

7:15 am-12:42 am

2 stops18h 27m

Winnipeg

sáb. 12/6

12:20 pm-9:21 am

2 stops20h 01m

$732

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

mié. 12/3

6:05 am-3:07 pm

1 stop10h 02m

Winnipeg

dom. 12/7

5:45 pm-10:48 am

2 stops16h 03m

$733

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

vie. 12/5

6:05 am-4:55 pm

2 stops11h 50m

Winnipeg

dom. 12/7

6:40 am-6:40 pm

2 stops11h 00m

$814

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

vie. 12/5

6:05 am-4:55 pm

2 stops11h 50m

Winnipeg

lun. 12/8

5:45 pm-9:21 am

2 stops14h 36m

$819

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

jue. 12/4

7:15 am-11:44 pm

2 stops17h 29m

Winnipeg

dom. 12/7

5:45 pm-10:48 am

2 stops16h 03m

$819

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Compare providers for flights from Cleveland to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Cleveland to Winnipeg in November.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Cleveland-Winnipeg flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Cleveland-Winnipeg flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Cleveland-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Cleveland-Winnipeg flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Cleveland-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, March is the cheapest month in which you can book a flight from Cleveland to Winnipeg (average of $126). Flying from Cleveland to Winnipeg in February is currently the most expensive (average of $687). 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 noviembre 26, 2025.

It’s optimal to fly from Cleveland to Winnipeg in the morning. By choosing this option you can save up to 12% on the cost of your flight, compared to a flight in the evening.

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 noviembre 26, 2025.
Get a feel of what it's like to fly with 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.
United Airlines
7.4
Good
9,046 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,046 reviews
United Airlines
7.4
Good
9,046 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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.

  • How long is the flight from Cleveland to Winnipeg?

    Departing from Cleveland to Winnipeg will take you 19h 37m. There are 943 mi between Cleveland and Winnipeg.

  • What is the cheapest airline to fly from Cleveland to Winnipeg round-trip?

    According to our current data, United Airlines ($744), offers the cheapest pricing from Cleveland to Winnipeg. You may be able to fly from Cleveland to Winnipeg for 7% less than the average price by searching for this airline.

  • 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, March is the cheapest month in which you can book a flight from Cleveland to Winnipeg (average of $126). Flying from Cleveland to Winnipeg in February is currently the most expensive (average of $687). 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 airline flying from Cleveland to Winnipeg

Discover the top airline 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 noviembre 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$744Average$806FlexibilityNo cancel feeOn-time69%

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