Cheap Christmas and winter break flights from Boston
Christmas and winter break 2026: the cheapest round trips from Boston that travelers found recently, leaving December 12 to December 24 and coming back December 26 to January 6, with a carry-on counted in.
The cheapest is Miami for $276, Mon, Dec 21 to Wed, Dec 30 on JetBlue.
Live prices to Miami for those dates
Places to stay in Miami
Hotels and rentals in Miami for Mon, Dec 21 to Wed, Dec 30, with current prices on a map you can move around.
Real hotels and rentals from Stay22's booking partners. Dipt may earn a commission when you book.
Need a car in Miami?
Rental cars at MIA airport for Mon, Dec 21 to Wed, Dec 30, compared across rental companies by QEEQ.
Cars for drivers 25+ Cars for drivers 21–24
Under 25? Most rental companies add a young driver fee, often $20 to $50 a day, and the 21–24 button shows prices with it in. Some memberships waive it, like AAA at Hertz for ages 20 to 24. Under 21, few companies rent at all. Dipt may earn a commission.
Cheapest Christmas and winter break trips from Boston
| Where | Leave | Return | Airline | Stops | Total, carry-on incl. | Live prices | Places to stay | Rental cars |
|---|---|---|---|---|---|---|---|---|
| Miami | Mon, Dec 21 | Wed, Dec 30 | JetBlue | 2 stops | $276 | Live price | Stays | Car |
| Nashville | Sun, Dec 20 | Wed, Jan 6 | JetBlue | Nonstop | $290 | Live price | Stays | Car |
| Omaha | Mon, Dec 21 | Mon, Jan 4 | Southwest | 1 stop | $338 | Live price | Stays | Car |
| San Francisco | Thu, Dec 24 | Wed, Jan 6 | JetBlue | 2 stops | $393 | Live price | Stays | |
| Sarasota | Thu, Dec 17 | Tue, Dec 29 | American Airlines | 1 stop | $434 | Live price | Stays | Car |
| Punta Cana, Dominican Republic | Thu, Dec 17 | Tue, Jan 5 | JetBlue | 1 stop | $455 | Live price | Stays | Car |
| Cincinnati | Sun, Dec 20 | Wed, Jan 6 | Frontier | 1 stop | $492 | Live price | Stays | Car |
| Warsaw, Poland | Thu, Dec 24 | Tue, Jan 5 | SAS | 1 stop | $767 | Live price | Stays | Car |
| Manchester, UK | Wed, Dec 23 | Sun, Dec 27 | Icelandair | 1 stop | $863 | Live price | Stays | Car |
| Istanbul, Türkiye | Sat, Dec 12 | Sat, Dec 26 | United | 3 stops | $979 | Live price | Stays |
Flying home? Every city, A to Z
The cheapest round trip from Boston to each city with a fare for these dates.
| Where | Leave | Return | Airline | Stops | Total, carry-on incl. | Live prices | Places to stay | Rental cars |
|---|---|---|---|---|---|---|---|---|
| Budapest, Hungary | Sat, Dec 19 | Sun, Jan 3 | Air Canada | 3 stops | $1,563 | Live price | Stays | Car |
| Casablanca, Morocco | Sat, Dec 19 | Tue, Jan 5 | Air Canada | 2 stops | $1,797 | Live price | Stays | Car |
| Cincinnati | Sun, Dec 20 | Wed, Jan 6 | Frontier | 1 stop | $492 | Live price | Stays | Car |
| Dubai, United Arab Emirates | Sat, Dec 12 | Sat, Dec 26 | Lufthansa | 1 stop | $1,127 | Live price | Stays | Car |
| Dublin, Ireland | Sat, Dec 19 | Sun, Jan 3 | Aer Lingus | Nonstop | $1,397 | Live price | Stays | Car |
| Istanbul, Türkiye | Sat, Dec 12 | Sat, Dec 26 | United | 3 stops | $979 | Live price | Stays | |
| Lisbon, Portugal | Sat, Dec 19 | Sun, Jan 3 | Air Canada | 1 stop | $1,429 | Live price | Stays | Car |
| Manchester, UK | Wed, Dec 23 | Sun, Dec 27 | Icelandair | 1 stop | $863 | Live price | Stays | Car |
| Medellín, Colombia | Tue, Dec 15 | Tue, Jan 5 | JetBlue | 3 stops | $1,082 | Live price | Stays | |
| Miami | Mon, Dec 21 | Wed, Dec 30 | JetBlue | 2 stops | $276 | Live price | Stays | Car |
| Montego Bay, Jamaica | Fri, Dec 18 | Mon, Jan 4 | American Airlines | 2 stops | $1,155 | Live price | Stays | Car |
| Nashville | Sun, Dec 20 | Wed, Jan 6 | JetBlue | Nonstop | $290 | Live price | Stays | Car |
| Omaha | Mon, Dec 21 | Mon, Jan 4 | Southwest | 1 stop | $338 | Live price | Stays | Car |
| Phuket, Thailand | Sun, Dec 20 | Sun, Dec 27 | American Airlines | 2 stops | $1,693 | Live price | Stays | Car |
| Punta Cana, Dominican Republic | Thu, Dec 17 | Tue, Jan 5 | JetBlue | 1 stop | $455 | Live price | Stays | Car |
| San Francisco | Thu, Dec 24 | Wed, Jan 6 | JetBlue | 2 stops | $393 | Live price | Stays | |
| San Juan, Puerto Rico | Tue, Dec 22 | Sat, Jan 2 | Allegiant | 2 stops | $995 | Live price | Stays | Car |
| Sarasota | Thu, Dec 17 | Tue, Dec 29 | American Airlines | 1 stop | $434 | Live price | Stays | Car |
| Vienna, Austria | Sun, Dec 20 | Sun, Jan 3 | Air Canada | 2 stops | $1,591 | Live price | Stays | Car |
| Warsaw, Poland | Thu, Dec 24 | Tue, Jan 5 | SAS | 1 stop | $767 | Live price | Stays | Car |
| Zurich, Switzerland | Tue, Dec 22 | Tue, Dec 29 | Air Canada | 3 stops | $1,373 | Live price | Stays | Car |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast, especially around the holidays: check the live price before you book.
Questions about Christmas and winter break flights from Boston
What's the cheapest place to fly from Boston for Christmas?
Of the fares travelers found recently, the cheapest round trips with a carry-on are Miami ($276, Mon, Dec 21 to Wed, Dec 30), Nashville ($290, Sun, Dec 20 to Wed, Jan 6) and Omaha ($338, Mon, Dec 21 to Mon, Jan 4).
What day should I fly for Christmas?
Of the cheapest trips found from Boston, more leave on Saturday, December 12 than any other day. Flexible? Check live prices a day or two either side: around the holidays, one day can change the price a lot.
Do these prices include bags?
They include a carry-on both ways, using our estimate of each airline's fee. A checked bag usually costs extra (bringing gifts? add that to the price), even on long flights abroad on the cheapest fares, though some airlines like Emirates include one.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.