The best trips from Boston
Boston, MA flies out of Boston Logan International (BOS). Over the last 30 days the cheapest routes we priced from Boston were New York City (from $333), Orlando (from $372), Miami (from $415).
2 trips from Boston found this week · last one 5 hours ago · next search in 04:22 · New trips from Boston land here as our bot finds them.
Our best picks from Boston right now
Prices per person, round trip, taxes and fees included.
Most loved from Boston
Ranked by real clicks, hearts and shares in the last 7 days.
$633 $536 per person, round trip, taxes and fees included You save $97 (15%)
the highest fare we saw for these dates
$596 $372 per person, round trip, taxes and fees included You save $224 (38%)
the highest fare we saw for these dates
Also priced this week from Boston
The other finalists of the last refresh, cheapest fare we found per person.
| Destination | Dates | From | Nonstop |
|---|---|---|---|
| New York City | Nov 27–30, 2026 | $333 | yes |
| Orlando | Nov 27–30, 2026 | $372 | no |
| Miami | Nov 27–30, 2026 | $415 | no |
| Washington, D.C. | Nov 27–30, 2026 | $444 | yes |
| Fort Lauderdale | Nov 27–30, 2026 | $446 | no |
| Key West | Nov 27–30, 2026 | $469 | no |
| New Orleans | Nov 27–30, 2026 | $525 | yes |
| Chicago | Oct 16–18, 2026 | $535 | yes |
| Nassau and Paradise Island | Nov 27–30, 2026 | $619 | no |
| Asheville | Oct 16–18, 2026 | $643 | no |
| Nashville | Oct 16–18, 2026 | $644 | no |
| Great Smoky Mountains | Oct 16–18, 2026 | $748 | no |
Cheapest routes from Boston, last 30 days
| Destination | Lowest | Typical | Checks |
|---|---|---|---|
| New York City | $333 | $333 | 1 · nonstop seen |
| Orlando | $372 | $419 | 4 |
| Miami | $415 | $415 | 1 |
| Washington, D.C. | $444 | $444 | 1 · nonstop seen |
| Fort Lauderdale | $446 | $446 | 1 |
| Key West | $469 | $503 | 2 |
| New Orleans | $525 | $661 | 2 · nonstop seen |
| Chicago | $535 | $535 | 1 · nonstop seen |
| Nassau and Paradise Island | $619 | $619 | 1 |
| Asheville | $643 | $643 | 1 |
| Nashville | $644 | $644 | 1 |
| Great Smoky Mountains | $748 | $748 | 1 |
| Bar Harbor & Acadia | $756 | $756 | 1 |
| Destin & the Emerald Coast | $874 | $874 | 1 |
More trips from Boston
Every other trip page from Boston still ahead of its date.
- Key West, Nov 27–30, 2026 from $536 Just found
- Orlando, Oct 16–18, 2026 from $372 Just found
Questions about flying from Boston
Which airports do the trips from Boston use?
Boston Logan International (BOS). Fares are the cheapest round trip we found across them for the exact dates, per person, taxes and fees included.
How often do the Boston picks change?
Around the clock: our search runs every few minutes across the cities and new finds 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: New York City from $333, Orlando from $372, Miami from $415, Washington, D.C. from $444, Fort Lauderdale from $446, per person round trip.
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.