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$188+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — YWG
Apr 6 — Apr 131
Mon 4/6
Mon 4/13
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 March 7, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/2. 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 4/168:55 pm
CLE
-
YWG
1 stop19h 14m
Multiple Airlines
Thu 4/238:05 pm
YWG
-
CLE
2 stops27h 38m
Multiple Airlines
Deal found 3/2$365
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 4/1711:01 am
CLE
-
YWG
2 stops14h 39m
Multiple Airlines
Sun 4/197:30 am
YWG
-
CLE
1 stop25h 09m
Multiple Airlines
Deal found 3/5$427
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Wed 4/15:30 am
CLE
-
YWG
1 stop10h 39m
Multiple Airlines
Wed 4/87:30 am
YWG
-
CLE
1 stop14h 49m
Multiple Airlines
Deal found 3/2$470
This United Airlines deal was found by Cheapflights users on 3/2. 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 4/163:08 pm
CLE
-
YWG
2 stops21h 44m
United Airlines
Thu 4/232:00 pm
YWG
-
CLE
2 stops18h 52m
United Airlines
Deal found 3/2$637
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 4/38:50 pm
CLE
-
YWG
2 stops43h 19m
Multiple Airlines
Fri 4/107:30 am
YWG
-
CLE
1 stop14h 49m
Multiple Airlines
Deal found 3/6$639
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 4/26:57 pm
CLE
-
YWG
1 stop31h 29m
Multiple Airlines
Tue 5/512:00 pm
YWG
-
CLE
2 stops28h 53m
Multiple Airlines
Deal found 3/4$640
This Air Canada deal was found by Cheapflights users on 3/3. 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 5/510:00 am
CLE
-
YWG
1 stop7h 18m
Air Canada
Wed 5/611:00 am
YWG
-
CLE
1 stop6h 23m
Air Canada
Deal found 3/3$641
This United Airlines deal was found by Cheapflights users on 3/5. 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 4/1712:15 pm
CLE
-
YWG
2 stops9h 42m
United Airlines
Sun 4/192:00 pm
YWG
-
CLE
2 stops8h 59m
United Airlines
Deal found 3/5$659

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 March 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$365
(Kiwi.com)

One-way from

$188
(Kiwi.com)
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.
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From Cleveland Hopkins Intl to Winnipeg
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One-way flight from Cleveland Hopkins Intl to Winnipeg
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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 March 7, 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

Thu 4/16

8:55 pm-3:09 pm

1 stop19h 14m

Winnipeg

Thu 4/23

8:05 pm-12:43 am

2 stops27h 38m

$365

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 4/17

11:01 am-12:40 am

2 stops14h 39m

Winnipeg

Sun 4/19

7:30 am-9:39 am

1 stop25h 09m

$427

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Wed 4/1

5:30 am-3:09 pm

1 stop10h 39m

Winnipeg

Wed 4/8

7:30 am-11:19 pm

1 stop14h 49m

$470

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Thu 4/16

3:08 pm-11:52 am

2 stops21h 44m

Winnipeg

Thu 4/23

2:00 pm-9:52 am

2 stops18h 52m

$637

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 4/3

8:50 pm-3:09 pm

2 stops43h 19m

Winnipeg

Fri 4/10

7:30 am-11:19 pm

1 stop14h 49m

$639

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Thu 4/2

6:57 pm-1:26 am

1 stop31h 29m

Winnipeg

Tue 5/5

12:00 pm-5:53 pm

2 stops28h 53m

$640
Quickest round-trip

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Tue 5/5

10:00 am-2:18 pm

1 stop5h 18m

Winnipeg

Wed 5/6

11:00 am-6:23 pm

1 stop6h 23m

$641

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 4/17

12:15 pm-8:57 pm

2 stops9h 42m

Winnipeg

Sun 4/19

2:00 pm-11:59 pm

2 stops8h 59m

$659

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Thu 4/2

7:00 am-11:52 am

1 stop5h 52m

Winnipeg

Tue 5/5

2:00 pm-10:20 pm

1 stop7h 20m

$663
Cheapest one-way

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Sun 4/19

9:57 pm-12:40 am

2 stops27h 43m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/4

Showing 1-10 of 11 resultsSorted by cheapest first
1
2
  • 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.

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, May is the cheapest month in which you can book a flight from Cleveland to Winnipeg (average of $149). Flying from Cleveland to Winnipeg in November is currently the most expensive (average of $608). 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.

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.

  • 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, May is the cheapest month in which you can book a flight from Cleveland to Winnipeg (average of $149). Flying from Cleveland to Winnipeg in November is currently the most expensive (average of $608). 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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