Search Cheap Flights to
Chesterland

Photo by Kristin DePlatchett

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Chesterland Flights as Low as $88

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Wed, Jul 16 - Sat, Jul 19
LGA
LaGuardia
CLE
Hopkins Intl.
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Jul 16 from LaGuardia to Hopkins Intl., returning Sat, Jul 19, priced at $88 found 3 days ago
Frontier Airlines
Wed, Jul 30 - Wed, Aug 6
LGA
LaGuardia
CLE
Hopkins Intl.
$90 Roundtrip, found 3 days ago
$90
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Jul 30 from LaGuardia to Hopkins Intl., returning Wed, Aug 6, priced at $90 found 3 days ago
Frontier Airlines
Thu, Jul 24 - Sun, Jul 27
PHL
Philadelphia Intl.
CLE
Hopkins Intl.
$91 Roundtrip, found 3 days ago
$91
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Jul 24 from Philadelphia Intl. to Hopkins Intl., returning Sun, Jul 27, priced at $91 found 3 days ago
Frontier Airlines
Tue, Aug 19 - Sat, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
CLE
Hopkins Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to Hopkins Intl., returning Sat, Aug 23, priced at $100 found 1 day ago
Spirit Airlines
Sat, Aug 2 - Sat, Aug 9
ATL
Hartsfield-Jackson Atlanta Intl.
CLE
Hopkins Intl.
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Aug 2 from Hartsfield-Jackson Atlanta Intl. to Hopkins Intl., returning Sat, Aug 9, priced at $118 found 2 days ago
Delta
Wed, Aug 13 - Wed, Aug 20
LGA
LaGuardia
CLE
Hopkins Intl.
$139 Roundtrip, found 3 days ago
$139
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Aug 13 from LaGuardia to Hopkins Intl., returning Wed, Aug 20, priced at $139 found 3 days ago
American Airlines
Wed, Aug 13 - Wed, Aug 20
LGA
LaGuardia
CLE
Hopkins Intl.
$139 Roundtrip, found 3 days ago
$139
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Aug 13 from LaGuardia to Hopkins Intl., returning Wed, Aug 20, priced at $139 found 3 days ago
United
Wed, Aug 13 - Wed, Aug 20
LGA
LaGuardia
CLE
Hopkins Intl.
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Select United flight, departing Wed, Aug 13 from LaGuardia to Hopkins Intl., returning Wed, Aug 20, priced at $159 found 3 days ago
Frontier Airlines
Mon, Jul 28 - Mon, Aug 4
DFW
Dallas-Fort Worth Intl.
CLE
Hopkins Intl.
$163 Roundtrip, found 3 days ago
$163
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Jul 28 from Dallas-Fort Worth Intl. to Hopkins Intl., returning Mon, Aug 4, priced at $163 found 3 days ago
Frontier Airlines
Fri, Sep 26 - Mon, Sep 29
IAH
George Bush Intercontinental
CLE
Hopkins Intl.
$187 Roundtrip, found 4 days ago
$187
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Sep 26 from George Bush Intercontinental to Hopkins Intl., returning Mon, Sep 29, priced at $187 found 4 days ago
Delta
Tue, Oct 7 - Tue, Oct 14
DAL
Love Field
CLE
Hopkins Intl.
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Oct 7 from Love Field to Hopkins Intl., returning Tue, Oct 14, priced at $217 found 4 days ago
Frontier Airlines
Thu, Sep 4 - Mon, Sep 8
LAX
Los Angeles Intl.
CLE
Hopkins Intl.
$225 Roundtrip, found 6 days ago
$225
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Los Angeles Intl. to Hopkins Intl., returning Mon, Sep 8, priced at $225 found 6 days ago
Frontier Airlines
Fri, Jul 11 - Sat, Jul 12
TTN
Mercer
CLE
Hopkins Intl.
$284 Roundtrip, found 16 hours ago
$284
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Fri, Jul 11 from Mercer to Hopkins Intl., returning Sat, Jul 12, priced at $284 found 16 hours ago
American Airlines
Sat, Aug 16 - Mon, Aug 18
CWA
Central Wisconsin
CLE
Hopkins Intl.
$307 Roundtrip, found 16 hours ago
$307
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Sat, Aug 16 from Central Wisconsin to Hopkins Intl., returning Mon, Aug 18, priced at $307 found 16 hours ago
Alaska Airlines
Thu, Sep 4 - Fri, Sep 12
LAX
Los Angeles Intl.
CLE
Hopkins Intl.
$308 Roundtrip, just found
$308
Roundtrip
just found
Select Alaska Airlines flight, departing Thu, Sep 4 from Los Angeles Intl. to Hopkins Intl., returning Fri, Sep 12, priced at $308 just found
JetBlue Airways
Tue, Aug 19 - Sat, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
CLE
Hopkins Intl.
$319 Roundtrip, found 1 day ago
$319
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to Hopkins Intl., returning Sat, Aug 23, priced at $319 found 1 day ago

Cheap Flights to Chesterland

Fall in love at first flight with your vacation to Chesterland by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chesterland on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chesterland, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chesterland

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chesterland with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CLE airport.

What is the cheapest month to fly to Chesterland?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chesterland are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chesterland?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Chesterland.

What airport is best to fly into Chesterland?

When you’re planning your trip to Chesterland, convenience is the name of the game. Luckily, Chesterland Cuyahoga County Airport is nearby so you can deplane and get going on checking off everything on your Chesterland must-do list.

How much are flights to Chesterland?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chesterland on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $88, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chesterland?

The trick to saving a stack of cash on your flight to Chesterland? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $88 right now, why wait?

Chesterland Flight Information
Destination airport
Hopkins Intl.
Destination airport IATA code
CLE
Roundtrip price
$88

Last Minute Hotel Deals in Chesterland

The Westin Cleveland Downtown
The Westin Cleveland Downtown
4 out of 5
777 Saint Clair Ave Ne, Cleveland, OH
Book a stay at this business-friendly hotel in Cleveland. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,413 reviews)
"Great night in a top class hotel."

Reviewed on Jul 2, 2025

Get rates
The Westin Cleveland Downtown
Hotel Indigo Cleveland Downtown by IHG
Hotel Indigo Cleveland Downtown by IHG
3.5 out of 5
651 Huron Rd E, Cleveland, OH
Stay at this 3.5-star business-friendly hotel in Cleveland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.4/10 Very Good! (1,185 reviews)
"Power must have been out recently hotel lobby was hot, elevators hot, hallways hot, room waa not aa hot. Could have been very bad but survived. Location was great"

Reviewed on Jul 4, 2025

Get rates
Hotel Indigo Cleveland Downtown by IHG
Extended Stay America Premier Suites - Cleveland - Independence
Extended Stay America Premier Suites - Cleveland - Independence
2.5 out of 5
6025 Jefferson Dr, Independence, OH
Book a stay at this business-friendly hotel in Independence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.4/10 Good! (1,622 reviews)
"It was clean and comfortable for me. I booked two beds but they “overbooked” so my grandson had to sleep on a sofa bed! Felt like bait and switch tactic to me. Breakfast was granola bars or packaged muffins. Pool is closed permanently."

Reviewed on Jun 27, 2025

Get rates
Extended Stay America Premier Suites - Cleveland - Independence
Hyatt Regency Cleveland At The Arcade
Hyatt Regency Cleveland At The Arcade
4 out of 5
420 Superior Ave E, Cleveland, OH
Stay at this 4-star eco-certified hotel in Cleveland. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,000 reviews)
Would stay here again
"Comfortable with nice amenities. Enjoyed the restaurants on site. Experience was very good overall. Only downsides were: temperature fluctuations (set thermostat to a comfortable temp, but room went from hot to cold all night) and rooms had motion sensor nightlights that turned on throughout the ..."

Reviewed on Jul 2, 2025

Get rates
Hyatt Regency Cleveland At The Arcade
Drury Plaza Hotel Cleveland Downtown
Drury Plaza Hotel Cleveland Downtown
3 out of 5
1380 East 6th Street, Cleveland, OH
Stay at this 3-star hotel in Cleveland. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.4/10 Exceptional! (2,504 reviews)
Nice place to stay
"It was good. Bed wasn't the most comfortable. I think it was. A spring matress that had seen better days. Walk in shower was good. Included dinner and breakfast was great"

Reviewed on Jul 2, 2025

Get rates
Drury Plaza Hotel Cleveland Downtown
Hilton Cleveland Downtown
Hilton Cleveland Downtown
4 out of 5
100 Lakeside Ave East, Cleveland, OH
Stay at this 4-star business-friendly hotel in Cleveland. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the bar and the helpful ...
9/10 Wonderful! (1,060 reviews)
"Great view and walking distance to the Rock and Roll hall of fame and Huntingyon bank field"

Reviewed on Jul 3, 2025

Get rates
Hilton Cleveland Downtown
Wyndham Independence
Wyndham Independence
4 out of 5
6200 Quarry Lane, Independence, OH
Stay at this 4-star business-friendly hotel in Independence. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Cleveland Metroparks Zoo ...
6.4/10 (1,005 reviews)
Not terrible.
"The AC in the building wasn’t working. It was soo hot. There is only one elevator on each side of the building and the elevator half worked. A lot of the times we had to stand and wait for 10 minutes at least to get the elevator to us and it was sketchy to be on. Was able to use the outside pool ..."

Reviewed on Jul 2, 2025

Get rates
Wyndham Independence
Fidelity Hotel
Fidelity Hotel
4 out of 5
1940 East 6th Street, Cleveland, OH
Stay at this 4-star hotel in Cleveland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Progressive Field and Rock ...
9.6/10 Exceptional! (215 reviews)
"Friendly staff and great location."

Reviewed on Jul 4, 2025

Get rates
Fidelity Hotel
See all 1,350 properties in Chesterland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.