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Cheap flights from Cleveland to Winnipeg from C$ 105

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 25/10. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — YWG
11 Oct — 18 Oct1
1 adult
1 adult, Economy

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 11 September 2025.

Round-trip from

C$ 374

One-way from

C$ 105

Popular in

November

Cheapest in

January

Average price

C$ 1,232
31/10-9/11
  • 31/10-9/11
  • 3 total stops
  • 57h 42m total
  • Cleveland to Winnipeg
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25/10
  • 25/10
  • 1 total stop
  • 20h 28m total
  • Cleveland to Winnipeg
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Highest demand for flights based on searches. 2% potential increase in price (C$ 37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 51 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 11 September 2025.

Fri 31/107:51 p.m.CLE - YWG
2 stops29h 50mMultiple Airlines
Sun 9/117:30 a.m.YWG - CLE
1 stop27h 52mMultiple Airlines
Deal found 8/9C$ 374
Fri 24/107:39 p.m.CLE - YWG
2 stops23h 01mMultiple Airlines
Fri 31/107:30 a.m.YWG - CLE
1 stop16h 24mMultiple Airlines
Deal found 8/9C$ 387
Sat 1/115:45 p.m.CLE - YWG
2 stops23h 22mMultiple Airlines
Sun 9/117:30 a.m.YWG - CLE
1 stop27h 52mMultiple Airlines
Deal found 8/9C$ 416
Sat 1/119:22 p.m.CLE - YWG
1 stop29h 21mMultiple Airlines
Mon 10/119:00 p.m.YWG - CLE
2 stops16h 14mMultiple Airlines
Deal found 8/9C$ 427
Mon 22/97:34 p.m.CLE - YWG
2 stops24h 49mMultiple Airlines
Thu 25/99:00 a.m.YWG - CLE
1 stop24h 39mMultiple Airlines
Deal found 8/9C$ 470

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 11 September 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

Fri 31/10

7:51 p.m.-12:41 a.m.

2 stops29h 50m

Winnipeg

Sun 9/11

7:30 a.m.-12:22 p.m.

1 stop27h 52m

C$ 374

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Sat 1/11

9:22 p.m.-1:43 a.m.

1 stop29h 21m

Winnipeg

Mon 10/11

9:00 p.m.-2:14 p.m.

2 stops16h 14m

C$ 427

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Sat 1/11

9:22 p.m.-1:43 a.m.

1 stop29h 21m

Winnipeg

Sun 9/11

7:30 a.m.-12:22 p.m.

1 stop27h 52m

C$ 430

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Mon 22/9

7:34 p.m.-7:23 p.m.

2 stops24h 49m

Winnipeg

Thu 25/9

9:00 a.m.-10:39 a.m.

1 stop24h 39m

C$ 470

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Fri 24/10

7:56 p.m.-6:32 p.m.

2 stops23h 36m

Winnipeg

Fri 31/10

12:55 p.m.-8:33 p.m.

3 stops30h 38m

C$ 531

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Mon 19/1

12:15 p.m.-12:42 a.m.

2 stops37h 27m

Winnipeg

Mon 26/1

8:00 a.m.-11:20 a.m.

1 stop26h 20m

C$ 540

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Sat 25/10

7:39 p.m.-3:07 p.m.

1 stop20h 28m

C$ 105

ClevelandWinnipeg

CLE - YWG

CLEYWG

Cleveland Hopkins Intl

Sun 19/10

5:45 a.m.-12:30 a.m.

2 stops19h 45m

C$ 169

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

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, January is the cheapest month in which you can book a flight from Cleveland to Winnipeg (average of C$ 123). Flying from Cleveland to Winnipeg in July is currently the most expensive (average of C$ 232). 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, January is the cheapest month in which you can book a flight from Cleveland to Winnipeg (average of C$ 123). Flying from Cleveland to Winnipeg in July is currently the most expensive (average of C$ 232). 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

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Fly with Cheapflights

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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.

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