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$606+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — YWG
Aug 15 — Aug 221
Sat 8/15
Sat 8/22
1 adult, Economy
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Cheap 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 July 16, 2026.

This Air Canada deal was found by Cheapflights users on 7/10. 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.
Fri 9/112:45 pm
CLE
-
YWG
1 stop7h 29m
Air Canada
Tue 9/1510:50 am
YWG
-
CLE
1 stop6h 33m
Air Canada
Deal found 7/10$606
This oojo deal was found by Cheapflights users on 7/11. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:26 am
CLE
-
YWG
2 stops12h 59m
WestJet
Wed 8/127:00 am
YWG
-
CLE
2 stops15h 21m
WestJet
Deal found 7/11$628
This United Airlines deal was found by Cheapflights users on 7/10. 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.
Fri 9/1110:37 am
CLE
-
YWG
2 stops12h 56m
United Airlines
Tue 9/152:00 pm
YWG
-
CLE
2 stops8h 54m
United Airlines
Deal found 7/10$629
This United deal was found by Cheapflights users on 7/11. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/510:53 am
CLE
-
YWG
1 stop12h 45m
Multiple Airlines
Wed 8/1210:55 am
YWG
-
CLE
1 stop6h 28m
Multiple Airlines
Deal found 7/11$635
This oojo deal was found by Cheapflights users on 7/15. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:26 am
CLE
-
YWG
2 stops10h 59m
WestJet
Mon 8/317:10 pm
YWG
-
CLE
2 stops13h 45m
WestJet
Deal found 7/15$637
This Air Canada deal was found by Cheapflights users on 7/11. 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.
Thu 7/3010:00 am
CLE
-
YWG
1 stop7h 20m
Air Canada
Wed 8/510:55 am
YWG
-
CLE
1 stop6h 28m
Air Canada
Deal found 7/11$639
This United Airlines deal was found by Cheapflights users on 7/11. 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.
Thu 8/67:00 am
CLE
-
YWG
1 stop5h 52m
United Airlines
Fri 8/147:00 am
YWG
-
CLE
1 stop15h 59m
United Airlines
Deal found 7/11$642

Find 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 July 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$606
(Air Canada)
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

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 July 16, 2026.
Use the filters below to find and compare flights from Cleveland to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 9/11

10:37 am-10:33 pm

2 stops12h 56m

Winnipeg

Tue 9/15

2:00 pm-11:54 pm

2 stops8h 54m

$629

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 9/11

2:45 pm-11:17 pm

2 stops9h 32m

Winnipeg

Tue 9/15

10:50 am-6:23 pm

1 stop6h 33m

$630

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Thu 7/30

6:00 am-11:52 am

1 stop6h 52m

Winnipeg

Wed 8/5

7:00 am-11:49 pm

1 stop15h 49m

$642

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Thu 8/6

7:00 am-11:52 am

1 stop5h 52m

Winnipeg

Fri 8/14

7:00 am-11:59 pm

1 stop15h 59m

$642
Quickest round-trip

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 7/31

7:00 am-11:52 am

1 stop5h 52m

Winnipeg

Tue 8/4

10:55 am-6:23 pm

1 stop6h 28m

$646

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Wed 8/5

2:05 pm-10:38 pm

1 stop9h 33m

Winnipeg

Wed 8/12

5:00 am-6:23 pm

2 stops12h 23m

$649

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/10

Sorted by cheapest first

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 July.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Cleveland-Winnipeg flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

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 9h 32m. There are 943 mi between Cleveland and Winnipeg. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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.

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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