Cheap flights from Cleveland to Winnipeg from C$ 298
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 29/12. Fares are subject to change and may not be available on all flights or dates of travel.
Find flight deals from Cleveland to Winnipeg
Cheapest flights from Cleveland to WinnipegExplore 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 October 2025.
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 October 2025.
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 29 October 2025.
Cheapflights Fare Finder
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
ClevelandWinnipeg
CLE - YWG
CLEYWG
Cleveland Hopkins Intl
Fri 21/11
5:30 a.m.-3:07 p.m.
1 stop10h 37m
Winnipeg
Mon 24/11
9:00 p.m.-10:32 a.m.
2 stops12h 32m
ClevelandWinnipeg
CLE - YWG
CLEYWG
Cleveland Hopkins Intl
Sun 21/12
2:30 p.m.-1:23 a.m.
1 stop11h 53m
Winnipeg
Fri 26/12
7:30 a.m.-4:30 p.m.
1 stop8h 00m
ClevelandWinnipeg
CLE - YWG
CLEYWG
Cleveland Hopkins Intl
Mon 22/12
11:26 a.m.-11:50 p.m.
2 stops37h 24m
Winnipeg
Fri 26/12
7:30 a.m.-4:30 p.m.
1 stop8h 00m
ClevelandWinnipeg
CLE - YWG
CLEYWG
Cleveland Hopkins Intl
Tue 10/3
6:10 p.m.-11:54 p.m.
1 stop6h 44m
Winnipeg
Wed 11/3
11:05 a.m.-5:30 p.m.
1 stop5h 25m
ClevelandWinnipeg
CLE - YWG
CLEYWG
Cleveland Hopkins Intl
Tue 10/3
7:00 a.m.-11:43 a.m.
1 stop5h 43m
Winnipeg
Wed 11/3
12:40 p.m.-12:37 a.m.
2 stops10h 57m
ClevelandWinnipeg
CLE - YWG
CLEYWG
Cleveland Hopkins Intl
Tue 10/3
6:53 a.m.-11:39 a.m.
1 stop5h 46m
Winnipeg
Wed 11/3
2:15 p.m.-11:28 p.m.
2 stops8h 13m
ClevelandWinnipeg
CLE - YWG
CLEYWG
Cleveland Hopkins Intl
Mon 29/12
5:25 p.m.-8:06 p.m.
3 stops51h 41m
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.
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$ 176). Flying from Cleveland to Winnipeg in February is currently the most expensive (average of C$ 960). 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.
How much does it cost to fly round-trip from Cleveland to Winnipeg?
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.
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Alternative routes for Cleveland to Winnipeg
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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.