Worth it from Cleveland this week, from £100
Cleveland flies out of one airport, Cleveland Hopkins International (CLE), which keeps things simple. For a long weekend, Toronto is 190 miles away, and Washington, D.C., Chicago and Philadelphia sit between 304 and 358 miles out. New York City, at 404 miles, has a nonstop too. For the longer trips, Orlando had the lowest fare we found, $107 per person nonstop when we checked. The heads-up: Miami, Key West and Los Angeles all mean a stop, so plan for the extra travel time.
14 new picks from Cleveland this week · last one 4 hours ago · next check in 01:20 · New picks from Cleveland land here as we find them.
Our picks from Cleveland right now
Each with the reasons, the catch and the total before you go.
Next weekend · from ClevelandNot worth it this week
New York City
23 – 25 Oct 2026 · 2 nights
- Highs of 55–68°F with rain chances of 11% to 17%
- The Cloud One scores 8.8 from 7,951 reviews
- United nonstop in 92 minutes at $387 per person
£1,373 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £510 + hotel £761 + resort fee £103, taxes in · a checked bag each adds about £181
Frontier · with a stop · 5h 42m
The catch: The Frontier fare is $34 per person above the typical $304, with one stop and 5h 42m out; a checked bag is about $240 for two.
Worth it if your dates are fixed and one stop doesn't bother you; skip it if you can wait for the fare to come back down.
Tweak this trip
The weekend after · from Cleveland26% below typical
Orlando
30 Oct – 1 Nov 2026 · 2 nights
- Nonstop on Frontier in 2h 31m, landing at 3:58 PM
- $133 per person, $49 below the typical fare on this route
- Best Western Orlando Gateway Hotel, 7.7 from 5,799 reviews, free cancellation
£363 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £201 + hotel £146 + resort fee £17, taxes in · a checked bag each adds about £181
Frontier · nonstop · 2h 31m
The catch: A checked bag is about $240 for two and isn't in the $482, and the normals for Sunday, Nov 1 show drizzle.
Worth it if you want a quick theme-park weekend near Universal and can pack light; skip it if you need checked bags or a slow pace.
Tweak this trip
Nine nights away · from ClevelandWorth it, if
Honolulu & Oahu
14 – 23 Nov 2026 · 9 nights
- $682 per person, $430 below the highest fare we saw
- Typical highs of 81–82°F and lows near 73°F in mid-November
- Aqua Aloha Surf Waikiki: 7.5 from 1,237 reviews, free cancellation
£2,192 for two · 9 nights · flights, hotel, taxes, fees & the resort fee
Flights £1,028 + hotel £1,006 + resort fee £158, taxes in · a checked bag each adds about £121
United · with a stop · 12h 27m
The catch: There's no nonstop: the outbound has one stop and takes 12h 27m, the seasonal normals show drizzle most days, and a checked bag runs about $160 for two.
Worth it if you want nine warm beach days and can sit through a 12h 27m travel day; skip it if you need a nonstop.
Tweak this trip
Most loved from Cleveland
What readers clicked, hearted and shared in the last 7 days.
Just found · from Cleveland25% below typicalWorth it, if
Great Smoky Mountains
30 Oct – 1 Nov 2026 · 2 nights
- $365 per person, $122 below the typical fare on this route
- Zoders Inn and Suites in Gatlinburg: 8.2 from 1,812 reviews
- Peak fall foliage weekend, with typical highs of 60–65°F
£788 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £549 + hotel £214 + resort fee £24, taxes in · a checked bag each adds about £181
F9 + G4 · with a stop · 26h 46m
The catch: One stop each way adds up to 26h 46m of travel, the return leaves at 7:00 AM, and a checked bag is about $240 for two.
Worth it if you want a fall foliage weekend in Gatlinburg and can handle long connections; skip it if long travel days wear you out.
Nine nights away · from ClevelandWorth it, if
Honolulu & Oahu
14 – 23 Nov 2026 · 9 nights
- $682 per person, $430 below the highest fare we saw
- Typical highs of 81–82°F and lows near 73°F in mid-November
- Aqua Aloha Surf Waikiki: 7.5 from 1,237 reviews, free cancellation
£2,192 for two · 9 nights · flights, hotel, taxes, fees & the resort fee
Flights £1,028 + hotel £1,006 + resort fee £158, taxes in · a checked bag each adds about £121
United · with a stop · 12h 27m
The catch: There's no nonstop: the outbound has one stop and takes 12h 27m, the seasonal normals show drizzle most days, and a checked bag runs about $160 for two.
Worth it if you want nine warm beach days and can sit through a 12h 27m travel day; skip it if you need a nonstop.
The weekend after · from Cleveland26% below typical
Orlando
30 Oct – 1 Nov 2026 · 2 nights
- Nonstop on Frontier in 2h 31m, landing at 3:58 PM
- $133 per person, $49 below the typical fare on this route
- Best Western Orlando Gateway Hotel, 7.7 from 5,799 reviews, free cancellation
£363 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £201 + hotel £146 + resort fee £17, taxes in · a checked bag each adds about £181
Frontier · nonstop · 2h 31m
The catch: A checked bag is about $240 for two and isn't in the $482, and the normals for Sunday, Nov 1 show drizzle.
Worth it if you want a quick theme-park weekend near Universal and can pack light; skip it if you need checked bags or a slow pace.
Also priced this week from Cleveland
The other finalists of the last refresh, cheapest fare we found per person.
| Destination | Dates | From | Nonstop |
|---|---|---|---|
| Miami | 13 – 17 Nov 2026 | £121 | no |
| Key West | 13 – 17 Nov 2026 | £186 | no |
| Los Angeles | 14 – 21 Nov 2026 | £207 | no |
| Washington, D.C. | 30 Oct – 1 Nov 2026 | £213 | no |
| Sedona | 14 – 21 Nov 2026 | £226 | no |
| Phoenix & Scottsdale | 14 – 21 Nov 2026 | £228 | no |
| Asheville | 30 Oct – 1 Nov 2026 | £236 | no |
| Great Smoky Mountains | 30 Oct – 1 Nov 2026 | £259 | no |
| Myrtle Beach | 30 Oct – 1 Nov 2026 | £279 | no |
| Chicago | 30 Oct – 1 Nov 2026 | £292 | yes |
| New Orleans | 23 – 25 Oct 2026 | £315 | no |
| Nashville | 30 Oct – 1 Nov 2026 | £325 | no |
Cheapest routes from Cleveland, last 30 days
| Destination | Lowest | Typical | Checks |
|---|---|---|---|
| Orlando | £81 | £137 | 21 · nonstop seen |
| Miami | £121 | £121 | 2 |
| New York City | £180 | £229 | 16 · nonstop seen |
| Key West | £186 | £186 | 1 |
| Los Angeles | £207 | £227 | 3 |
| Washington, D.C. | £213 | £452 | 5 |
| Sedona | £226 | £241 | 5 |
| Phoenix & Scottsdale | £228 | £246 | 5 |
| Asheville | £236 | £298 | 10 |
| Great Smoky Mountains | £259 | £367 | 14 |
| Myrtle Beach | £279 | £327 | 12 |
| Chicago | £292 | £446 | 12 · nonstop seen |
| New Orleans | £315 | £338 | 10 |
| Nashville | £325 | £400 | 10 |
| Cancún | £357 | £382 | 5 |
More trips from Cleveland
Every other trip page from Cleveland still ahead of its date.
- Great Smoky Mountains, 30 Oct – 1 Nov 2026 from £275 Just found
- New York City, 16 – 18 Oct 2026 from £277 Just found
- Sedona, 14 – 21 Nov 2026 from £250 Just found
- Chicago, 16 – 18 Oct 2026 from £297 Just found
- Phoenix & Scottsdale, 14 – 21 Nov 2026 from £248 Just found
- Asheville, 16 – 18 Oct 2026 from £296 Just found
- Miami, 13 – 17 Nov 2026 from £121 Just found
- Los Angeles, 14 – 21 Nov 2026 from £207
- New Orleans, 23 – 25 Oct 2026 from £315
- New Orleans, 16 – 18 Oct 2026 from £324 Just found
- Orlando, 16 – 18 Oct 2026 from £212 Just found
Questions about flying from Cleveland
Which airports do the trips from Cleveland use?
Cleveland Hopkins International (CLE). Fares are the cheapest return we found across them for the exact dates, per person, taxes and fees included.
How often do the Cleveland picks change?
Around the clock: we check live prices every few minutes across the cities and new picks from Cleveland land on this page as they are published. A pick stays until its departure date, then moves to the archive with the price it had.
What are the cheapest places to fly from Cleveland right now?
In the last 30 days: Orlando from £81, Miami from £121, New York City from £180, Key West from £186, Los Angeles from £207, per person return.
Can I ask for a specific trip?
Yes. Use the Ask box: say the destination or the kind of trip and the dates, and a page with live prices appears under Cleveland within a few minutes.
Planning something from Cleveland?
Tell us what the trip is for and we pick the one that’s worth it.
Prices converted from US dollars at the rate of 15 Oct 2026.