Weekend trips from Boston under $500
For each of the coming weekends, the cheapest return we hold from Boston to each place: out on a Thursday, Friday or Saturday and back on the Sunday or Monday, with at least a full day there.
Places with a weekend trip: 12
Weekends covered: 9
Weekend of Sat 21 Nov
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Fort Lauderdale | $298 | Thu 19 Nov 11:39 | Sun 22 Nov 07:20 | 2 weekdays | BOS → FLL | out nonstop, back nonstop | Allegiant Air | found 5 days ago | See prices for these dates | Check today's price |
| Cleveland | $353 | Fri 20 Nov 09:25 | Sun 22 Nov 18:21 | 1 weekday | BOS → CLE | out 1 stop, back 1 stop | Frontier Airlines | found 4 days ago | See prices for these dates | Check today's price |
Weekend of Sat 28 Nov
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Santiago | $423 | Thu 26 Nov 07:20 | Mon 30 Nov 12:55 | 3 weekdays | BOS → STI | out 1 stop, back 2 stops | United Airlines | found 5 days ago | See prices for these dates | Check today's price |
Weekend of Sat 5 Dec
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Miami | $294 | Fri 4 Dec 18:05 | Sun 6 Dec 06:55 | None | BOS → MIA | out nonstop, back 1 stop | American Airlines | found 2 days ago | See prices for these dates | Check today's price |
| San Francisco | $306 | Fri 4 Dec 18:13 | Mon 7 Dec 06:00 | 1 weekday | BOS → SFO | out 1 stop, back 1 stop | Alaska Airlines | found 3 days ago | See prices for these dates | Check today's price |
| Los Angeles | $312 | Thu 3 Dec 06:00 | Sun 6 Dec 10:00 | 2 weekdays | BOS → LAX | out nonstop, back 1 stop | jetBlue | found 5 days ago | See prices for these dates | Check today's price |
Weekend of Sat 12 Dec
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Fort Myers | $399 | Thu 10 Dec 11:00 | Mon 14 Dec 07:15 | 3 weekdays | BOS → RSW | out 1 stop, back 1 stop | United Airlines | found yesterday | See prices for these dates | Check today's price |
| Baltimore | $151 | Sat 12 Dec 05:25 | Mon 14 Dec 06:15 | 1 weekday | BOS → BWI | out nonstop, back 1 stop | Southwest Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Miami | $258 | Fri 11 Dec 18:05 | Sun 13 Dec 06:53 | None | BOS → MIA | out nonstop, back nonstop | American Airlines | found 6 days ago | See prices for these dates | Check today's price |
Weekend of Sat 19 Dec
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Fort Myers | $396 | Thu 17 Dec 10:40 | Mon 21 Dec 10:30 | 3 weekdays | BOS → RSW | out nonstop, back nonstop | jetBlue | found yesterday | See prices for these dates | Check today's price |
| Orlando | $224 | Thu 17 Dec 18:59 | Sun 20 Dec 14:53 | 1 weekday | PSM → SFB | out nonstop, back nonstop | Allegiant Air | found 6 days ago | See prices for these dates | Check today's price |
Weekend of Sat 9 Jan 2027
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Fort Myers | $296 | Thu 7 Jan 2027 11:30 | Sun 10 Jan 2027 07:00 | 2 weekdays | BOS → RSW | out 1 stop, back 1 stop | jetBlue | found 5 days ago | See prices for these dates | Check today's price |
Weekend of Sat 16 Jan 2027
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Fort Lauderdale | $305 | Fri 15 Jan 2027 11:39 | Mon 18 Jan 2027 05:43 | 2 weekdays | BOS → FLL | out 1 stop, back 1 stop | American Airlines | found yesterday | See prices for these dates | Check today's price |
Weekend of Sat 23 Jan 2027
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Austin | $268 | Thu 21 Jan 2027 08:00 | Sun 24 Jan 2027 12:50 | 2 weekdays | BOS → AUS | out nonstop, back nonstop | jetBlue | found 3 days ago | See prices for these dates | Check today's price |
Weekend of Sat 30 Jan 2027
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Sarasota | $176 | Fri 29 Jan 2027 10:57 | Mon 1 Feb 2027 07:01 | 2 weekdays | BOS → SRQ | out nonstop, back nonstop | Allegiant Air | found yesterday | See prices for these dates | Check today's price |
| Puebla | $491 | Thu 28 Jan 2027 07:40 | Sun 31 Jan 2027 08:24 | 2 weekdays | BOS → PBC | out 1 stop, back 1 stop | Volaris | found 6 days ago | See prices for these dates | Check today's price |
Every trip here gives at least 24 hours at the destination and gets you home by 6 am on the Tuesday. Times are local to each airport. "Weekdays off" counts Monday to Friday days the trip takes; a flight leaving at 5 pm or later does not take that day.
1 traveler · Economy
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work