CLE - YWG

$258 Find Cheap Flights from Cleveland to Winnipeg

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Cleveland to Winnipeg departing on 1/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Cleveland to Winnipeg, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Cleveland to Winnipeg, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$367
Multiple Airlines
Thu 1/8Thu 1/15
CLE - YWG • 2 stops
Cheapest one-way
Multiple Airlines
Thu 12/11
CLE - YWG • multi-stop
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Cleveland to Winnipeg (CLE-YWG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Cleveland to Winnipeg that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Cleveland to Winnipeg

Thu, Jan 8 - Thu, Jan 15
Multiple Airlines Logo
3:00 pm - 12:39 am
CLE
-
YWG
34h 39m2 stops
Multiple Airlines Logo
7:30 am - 2:07 pm
YWG
-
CLE
29h 37m1 stop
$367Multiple Airlines
Thu, Jan 8 - Thu, Jan 15
Multiple Airlines Logo
7:01 pm - 3:07 pm
CLE
-
YWG
21h 06m2 stops
Multiple Airlines Logo
9:00 pm - 6:06 pm
YWG
-
CLE
20h 06m3 stops
$409Multiple Airlines
Thu, Jan 8 - Thu, Jan 15
Multiple Airlines Logo
7:01 pm - 12:41 am
CLE
-
YWG
30h 40m3 stops
Multiple Airlines Logo
9:00 pm - 6:06 pm
YWG
-
CLE
20h 06m3 stops
$414Multiple Airlines
Sat, Mar 7 - Sat, Mar 21
Multiple Airlines Logo
6:06 pm - 2:09 pm
CLE
-
YWG
21h 03m1 stop
Multiple Airlines Logo
12:20 pm - 7:42 am
YWG
-
CLE
42h 22m2 stops
$425Multiple Airlines
Thu, Jan 8 - Thu, Jan 15
Multiple Airlines Logo
7:24 pm - 1:26 am
CLE
-
YWG
31h 02m1 stop
Multiple Airlines Logo
7:30 am - 2:07 pm
YWG
-
CLE
29h 37m1 stop
$581Multiple Airlines
Thu, Jan 8 - Thu, Jan 15
Multiple Airlines Logo
7:01 pm - 3:07 pm
CLE
-
YWG
21h 06m2 stops
Multiple Airlines Logo
12:20 pm - 6:06 pm
YWG
-
CLE
28h 46m2 stops
$597Multiple Airlines
Thu, Feb 5 - Mon, Feb 9
Air Canada Logo
6:10 pm - 11:54 pm
CLE
-
YWG
6h 44m1 stop
Air Canada Logo
11:05 am - 5:30 pm
YWG
-
CLE
5h 25m1 stop
$824Air Canada
Sat, Mar 7 - Sat, Mar 7
United Airlines Logo
7:02 am - 11:57 am
CLE
-
YWG
5h 55m1 stop
United Airlines Logo
2:20 pm - 10:15 pm
YWG
-
CLE
6h 55m1 stop
$826United Airlines
Thu, Feb 5 - Mon, Feb 9
United Airlines Logo
7:20 am - 11:57 am
CLE
-
YWG
5h 37m1 stop
United Airlines Logo
2:20 pm - 11:44 pm
YWG
-
CLE
8h 24m2 stops
$835United Airlines
Sat, Mar 7 - Sat, Mar 21
United Airlines Logo
7:59 pm - 10:57 am
CLE
-
YWG
15h 58m2 stops
United Airlines Logo
2:20 pm - 11:43 pm
YWG
-
CLE
8h 23m2 stops
$840United Airlines
Booking Insights

KAYAK's insights & trends for Cleveland to Winnipeg flights

Get data-powered insights and trends into flights from Cleveland to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Cleveland to Winnipeg?

The average price of all round-trip flights from Cleveland to Winnipeg clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Winnipeg on a Saturday and more expensive on a Friday. On your return trip to Cleveland, you should consider flying back on a Saturday, and avoid Thursdays for better deals.

Good to know

Cheapest flight$367
Flight from Cleveland to Winnipeg

When to book flights from Cleveland to Winnipeg

Are your dates flexible? Find out the best times to travel from Cleveland to Winnipeg based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Cleveland to Winnipeg

  • What is the cheapest flight from Cleveland to Winnipeg?

    In the last 3 days, the lowest price for a flight from Cleveland to Winnipeg was $258 for a round-trip ticket.

  • Do I need a passport to fly between Cleveland and Winnipeg?

    Yes

  • Which aircraft models fly most regularly from Cleveland to Winnipeg?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Cleveland to Winnipeg?

    Star Alliance is the only airline alliance operating flights between Cleveland and Winnipeg.

  • How does KAYAK find such low prices on flights from Cleveland to Winnipeg?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Cleveland to Winnipeg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Cleveland to Winnipeg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Cleveland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Cleveland to Winnipeg?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Cleveland with another airline. Booking your flights between Cleveland and YWG can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Cleveland to Winnipeg?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Cleveland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Cleveland to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Cleveland to Winnipeg. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Cleveland to Winnipeg? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9095 reviews
7.3Comfort
8.1Crew
6.6Food
7.1Entertainment
7.7Boarding
Airline reviews

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

8.0 ExcellentSteve, Dec 2025
DEN - YYZ
Read more United Airlines reviews

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

Very bad! They kept delaying my flight and wouldn’t do anything about it

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

Flight was good but there are way to many announcements for credit cards etc.

IAD with the archaic people movers is just a place to be avoided.

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

From the first moment you interact with United Airlines, you can expect nothing less but extreme frustration. The baggage handler at the bag drop seems completely unbothered by the presence of customers waiting in line. No help was extended to load the baggage whatsoever. And if any of your bags is overweight by 0.01 pound they will make you re-distribute everything in your suitcase just to play power trip. When it was time to board no help was extended to customers to locate their seats. Moreover. It was a chaotic mess at the gate when it was unclear who should board first and everyone just bunched up, trying to get on the plane. I am sure the crew was doing their best to perform their jobs while being paid their wages however it shouldn’t be that hard to smile once or twice when you’re in the business if serving customers. It is a shame for the United States of America to have a flagship carrier of such low caliber. Our flight was also delayed by about an hour and a half due to further delays prior to our inbound flight. Being someone who has travelled for both business and leisure in Asia, Europe, and South America I have never experienced such poor quality of service.

Everything you need to know for your flight from Cleveland to Winnipeg

Information on your arrival and departure airports