Worth it from Boston this week, from £253
Boston flies out of one airport, Boston Logan International (BOS), and plenty of good weekends start without it. Stowe is 167 miles away, New York City 187, Bar Harbor & Acadia 200, Montréal 250 (bring a passport) and Philadelphia 271. When flying is worth it, the all-in fares we found were nonstops to Orlando at $243, New York City at $297 and Chicago at $298. Longer trips take a stop: the Great Smoky Mountains at $319 and Los Angeles at $338. Fares change; these are what we found when we checked.
13 new picks from Boston this week · last one 31 min ago · next check in 02:44 · New picks from Boston land here as we find them.
Our picks from Boston right now
Each with the reasons, the catch and the total before you go.
Next weekend · from Boston17% below typicalWorth it, if
Nashville
23 – 25 Oct 2026 · 2 nights
- Frontier fare $409 per person, $86 below the typical fare on this route
- Highs of 76°F and 77°F Friday and Saturday, 4% and 8% rain
- Free cancellation and breakfast at a 7.9-rated hotel, $394 for two nights
£960 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £617 + hotel £297 + resort fee £46, taxes in · a checked bag each adds about £181
Frontier · with a stop · 8h 56m
The catch: The outbound has one stop and takes 8h 56m for a 942-mile trip, and a checked bag is about $240 for two, not in the total.
Worth it if a long travel day is fine for a lower-priced weekend of live music; skip it if you want a nonstop or a downtown hotel.
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The weekend after · from Boston48% below typicalWorth it, if
Great Smoky Mountains
30 Oct – 1 Nov 2026 · 2 nights
- Fare $336 per person, $312 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
£745 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £507 + hotel £214 + resort fee £24, taxes in · a checked bag each adds about £121
American. Operated by Piedmont Airlines as American Eagle · with a stop · 4h 26m
The catch: It's one stop and 4h 26m on the way down, rain or drizzle is typical for these dates, and a checked bag is about $160 for two.
Worth it if you want fall color and mountain hikes on a short weekend; skip it if crowds or wet trails would spoil the trip for you.
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Just found · from BostonWorth it, if
San Francisco
14 – 21 Nov 2026 · 7 nights
- Chelsea Inn, rated 8.2 by 1,885 guests
- Free cancellation at Chelsea Inn
- Typical highs 58–62°F, lows near 50°F this time of year
£1,927 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights £556 + hotel £1,202 + resort fee £169, taxes in · a checked bag each adds about £106
Alaska · with a stop · 18h 14m
The catch: Not nonstop: a stop on the way, 18h 14m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
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Most loved from Boston
What readers clicked, hearted and shared in the last 7 days.
Just found · from BostonLowest in 30 daysWorth it, if
Tokyo
14 – 23 Nov 2026 · 9 nights
- £297 per person below the typical fare on this route
- Lowest in 30 days on this route
- Urban Hotel Morisita, rated 8.1 by 267 guests
£2,322 for two · 9 nights · flights, hotel, taxes, fees & the resort fee
Flights £1,477 + hotel £775 + resort fee £70, taxes in · a checked bag each adds about £106
Air Canada · with a stop · 48h 38m
The catch: Not nonstop: a stop on the way, 48h 38m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
The weekend after · from Boston48% below typicalWorth it, if
Great Smoky Mountains
30 Oct – 1 Nov 2026 · 2 nights
- Fare $336 per person, $312 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
£745 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £507 + hotel £214 + resort fee £24, taxes in · a checked bag each adds about £121
American. Operated by Piedmont Airlines as American Eagle · with a stop · 4h 26m
The catch: It's one stop and 4h 26m on the way down, rain or drizzle is typical for these dates, and a checked bag is about $160 for two.
Worth it if you want fall color and mountain hikes on a short weekend; skip it if crowds or wet trails would spoil the trip for you.
Next weekend · from Boston17% below typicalWorth it, if
Nashville
23 – 25 Oct 2026 · 2 nights
- Frontier fare $409 per person, $86 below the typical fare on this route
- Highs of 76°F and 77°F Friday and Saturday, 4% and 8% rain
- Free cancellation and breakfast at a 7.9-rated hotel, $394 for two nights
£960 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £617 + hotel £297 + resort fee £46, taxes in · a checked bag each adds about £181
Frontier · with a stop · 8h 56m
The catch: The outbound has one stop and takes 8h 56m for a 942-mile trip, and a checked bag is about $240 for two, not in the total.
Worth it if a long travel day is fine for a lower-priced weekend of live music; skip it if you want a nonstop or a downtown hotel.
Also priced this week from Boston
The other finalists of the last refresh, cheapest fare we found per person.
| Destination | Dates | From | Nonstop |
|---|---|---|---|
| Orlando | 14 – 21 Nov 2026 | £183 | yes |
| New York City | 30 Oct – 1 Nov 2026 | £224 | yes |
| Chicago | 30 Oct – 1 Nov 2026 | £225 | yes |
| Los Angeles | 14 – 21 Nov 2026 | £255 | no |
| Phoenix & Scottsdale | 14 – 21 Nov 2026 | £262 | no |
| Sedona | 14 – 21 Nov 2026 | £262 | yes |
| Cancún | 14 – 21 Nov 2026 | £285 | no |
| Destin & the Emerald Coast | 30 Oct – 1 Nov 2026 | £291 | no |
| Miami | 27 – 30 Nov 2026 | £313 | no |
| New Orleans | 23 – 25 Oct 2026 | £315 | yes |
| Washington, D.C. | 23 – 25 Oct 2026 | £335 | yes |
| Fort Lauderdale | 27 – 30 Nov 2026 | £336 | no |
Cheapest routes from Boston, last 30 days
| Destination | Lowest | Typical | Checks |
|---|---|---|---|
| Orlando | £183 | £294 | 16 · nonstop seen |
| New York City | £224 | £354 | 9 · nonstop seen |
| Chicago | £225 | £291 | 11 · nonstop seen |
| Great Smoky Mountains | £240 | £488 | 10 |
| Los Angeles | £255 | £287 | 3 |
| San Francisco | £256 | £276 | 6 |
| Phoenix & Scottsdale | £262 | £274 | 6 |
| Sedona | £262 | £274 | 6 · nonstop seen |
| Cancún | £285 | £303 | 6 |
| Destin & the Emerald Coast | £291 | £549 | 11 |
| Nashville | £292 | £373 | 15 · nonstop seen |
| Miami | £313 | £313 | 1 |
| New Orleans | £315 | £430 | 8 · nonstop seen |
| Washington, D.C. | £335 | £413 | 4 · nonstop seen |
| Fort Lauderdale | £336 | £336 | 1 |
More trips from Boston
Every other trip page from Boston still ahead of its date.
- Tokyo, 14 – 23 Nov 2026 from £739 Just found
- Myrtle Beach, 16 – 18 Oct 2026 from £354 Just found
- Sedona, 14 – 21 Nov 2026 from £268 Just found
- Chicago, 16 – 18 Oct 2026 from £291 Just found
- Phoenix & Scottsdale, 14 – 21 Nov 2026 from £262 Just found
- Nashville, 16 – 18 Oct 2026 from £391 Just found
- Los Angeles, 14 – 21 Nov 2026 from £255
- New Orleans, 23 – 25 Oct 2026 from £315
- Key West, 27 – 30 Nov 2026 from £404 Just found
- Orlando, 16 – 18 Oct 2026 from £295 Just found
Questions about flying from Boston
Which airports do the trips from Boston use?
Boston Logan International (BOS). Fares are the cheapest return we found across them for the exact dates, per person, taxes and fees included.
How often do the Boston picks change?
Around the clock: we check live prices every few minutes across the cities and new picks from Boston 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 Boston right now?
In the last 30 days: Orlando from £183, New York City from £224, Chicago from £225, Great Smoky Mountains from £240, Los Angeles from £255, 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 Boston within a few minutes.
Planning something from Boston?
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.