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Cheap flights from Cleveland to Winnipeg from C$ 286

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 15/2. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — YWG
28 Feb — 7 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Cleveland to Winnipeg

Enter your travel dates to find the best prices.

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 29 January 2026.

Tue 3/27:02 p.m.
CLE
-
YWG
2 stops41h 30m
Multiple Airlines
Wed 11/27:30 a.m.
YWG
-
CLE
1 stop23h 04m
Multiple Airlines
Deal found 27/1C$ 664
Mon 2/27:21 p.m.
CLE
-
YWG
2 stops41h 11m
Multiple Airlines
Tue 10/28:00 a.m.
YWG
-
CLE
1 stop14h 09m
Multiple Airlines
Deal found 27/1C$ 938
Thu 9/47:00 a.m.
CLE
-
YWG
1 stop5h 52m
United Airlines
Sat 11/42:00 p.m.
YWG
-
CLE
1 stop5h 36m
United Airlines
Deal found 27/1C$ 996
Thu 9/412:27 p.m.
CLE
-
YWG
2 stops9h 30m
United Airlines
Thu 16/42:00 p.m.
YWG
-
CLE
1 stop8h 48m
United Airlines
Deal found 27/1C$ 1,010
Thu 19/26:10 p.m.
CLE
-
YWG
1 stop6h 44m
Air Canada
Mon 23/25:30 a.m.
YWG
-
CLE
1 stop11h 00m
Air Canada
Deal found 28/1C$ 1,033
Thu 19/26:00 a.m.
CLE
-
YWG
2 stops19h 35m
WestJet
Mon 23/29:00 p.m.
YWG
-
CLE
2 stops12h 48m
WestJet
Deal found 28/1C$ 1,109

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 29 January 2026.

Round-trip from

C$ 996

One-way from

C$ 286
United Airlines
  • United Airlines
  • 9/4-11/4
  • 2 total stops
  • 11h 28m total
  • Cleveland to Winnipeg
Search Deals
15/2
  • 15/2
  • 1 total stop
  • 8h 49m total
  • Cleveland 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 629,999 searches. Data last updated 29 January 2026.
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

Thu 9/4

7:00 a.m.-11:52 a.m.

1 stop5h 52m

Winnipeg

Sat 11/4

2:00 p.m.-8:36 p.m.

1 stop5h 36m

C$ 996

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Thu 9/4

7:00 a.m.-11:52 a.m.

1 stop5h 52m

Winnipeg

Thu 16/4

2:00 p.m.-11:48 p.m.

1 stop8h 48m

C$ 996

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Thu 19/2

6:10 p.m.-11:54 p.m.

1 stop6h 44m

Winnipeg

Mon 23/2

7:05 a.m.-5:30 p.m.

1 stop9h 25m

C$ 1,033

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Thu 19/2

1:00 p.m.-12:35 a.m.

2 stops12h 35m

Winnipeg

Mon 23/2

9:00 p.m.-10:48 a.m.

2 stops12h 48m

C$ 1,109

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Sun 15/2

7:20 a.m.-3:09 p.m.

1 stop8h 49m

C$ 286

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Sun 15/3

6:35 a.m.-11:01 a.m.

1 stop5h 26m

C$ 462

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Thu 9/4

7:00 a.m.-11:52 a.m.

1 stop5h 52m

C$ 462

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 13/3

7:02 a.m.-11:57 a.m.

1 stop5h 55m

C$ 462

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 13/3

6:05 a.m.-7:09 p.m.

2 stops14h 04m

C$ 494

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/1

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 C$ 171). Flying from Cleveland to Winnipeg in February is currently the most expensive (average of C$ 1,009). 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.

  • How long is the flight from Cleveland to Winnipeg?

    There are many flights that can get you from Cleveland to Winnipeg in 5h 52m. Fly via United Airlines or Air Canada to get the fastest option. Cleveland and Winnipeg are separated by a distance of 1518 km. When browsing for deals, the options you’ll see will be for both direct 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.

  • 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 C$ 171). Flying from Cleveland to Winnipeg in February is currently the most expensive (average of C$ 1,009). 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

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
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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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Cleveland to Winnipeg?

Cheapflights helps you search for flights from Cleveland to Winnipeg via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Cleveland to Winnipeg?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Cleveland to Winnipeg for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Cleveland to Winnipeg with no change fees?

Certainly. Search results for flights to Winnipeg from Cleveland shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Cleveland to Winnipeg become cheaper?

Yes, Cheapflights offers price alerts on Cleveland to Winnipeg flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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