Real December fare snapshots from New York, Chicago and Los Angeles show where a warm-weather escape can still be surprisingly affordable before the holidays.
Round trip economy fares in U.S. dollars from New York, Chicago, Dallas and Los Angeles. Snapshot checked September 26, 2026.
December has two very different airfare markets. The first half of the month can still look surprisingly reasonable, while Christmas and New Year's demand changes the equation quickly.
For this guide, we compared warm destinations from New York, Chicago and Los Angeles. Every destination below had at least one round-trip fare under $400, and every lowest fare we found departed by December 14. If your dates are flexible, early December is the obvious place to start.
| Destination | New York | Chicago | Dallas | Los Angeles | Dec high |
|---|---|---|---|---|---|
| San Juan, Puerto Rico | $247 | $172 | $198 | $233 | ~84°F |
| Cancún, Mexico | $276 | $262 | $270 | $353 | ~82°F |
| Aruba | $300 | $335 | $403 | $427 | ~83°F |
| Punta Cana, Dominican Republic | $302 | $316 | $433 | $472 | ~84°F |
| Puerto Vallarta, Mexico | $340 | $311 | $318 | $310 | ~85°F |
| Los Cabos, Mexico | $403 | $319 | $324 | $312 | ~75°F |
| Nassau, Bahamas | $306 | $331 | $389 | $341 | ~81°F |
| Willemstad, Curaçao | $348 | $349 | $602 | $529 | ~86°F |
| Guanacaste, Costa Rica | $366 | $388 | $452 | $474 | ~90°F |
| Cartagena, Colombia | $381 | $416 | $578 | $479 | ~88°F |
San Juan is the easiest warm city break on this list, and from Chicago it is also the cheapest ticket in the snapshot. At $172 round trip, the fare is low enough that a long weekend stops feeling like an indulgence.
Condado and Escambrón cover the swimming. Old San Juan covers the evenings. You can do both without treating the holiday as a transfer exercise. Typical December highs sit around 84°F, and U.S. travellers get the practical bonus of domestic-style entry.
Best for: a warm city-and-beach hybrid when the airfare from Chicago is the clear win.
Cancún remains the Midwest winter-sun default for a reason. At $262 from Chicago, you get deep flight inventory, every hotel style from all-inclusive towers to simpler stays, and day-trip options that do not require a complicated plan.
The Hotel Zone stays efficient. Isla Mujeres, Playa del Carmen or an inland day toward Valladolid change the texture if you want more than the pool. Typical highs around 82°F are beach weather without the sticky peak of deeper Caribbean heat.
Best for: an uncomplicated beach week with the widest accommodation range on this list.
Aruba may be the most weather-reliable pick in the Caribbean cluster. At $300 from New York, you are looking at dry-side heat sitting outside the main hurricane belt, which is exactly why December travellers keep returning.
Eagle Beach and Palm Beach handle the swimming days. Arikok National Park gives the island a desert-and-cactus texture that does not feel interchangeable with every other Caribbean stop. One practical warning: December is high season for hotels, so a strong airfare does not automatically mean a cheap vacation once accommodation is added.
Best for: dependable heat and beach days when weather reliability matters as much as price.
Punta Cana sits only $2 above Aruba from New York in this snapshot, which is almost absurd for a destination with this much resort inventory. This is the classic package beach trip: deep hotel choice, easy beach days, and enough flight frequency that the itinerary is rarely fragile.
If you want more than the resort strip, Playa Macao, Cap Cana and a day trip toward Saona change the week without requiring a complicated plan. Typical highs sit around 84°F. Compare hotel-inclusive quotes before treating the ticket as the whole deal.
Best for: a package-friendly beach week with familiar logistics.
From Los Angeles, Puerto Vallarta is the Pacific answer to Cancún. At $310, the fare is short-haul enough to feel casual, and the destination mixes a walkable centro with beach towns along Banderas Bay.
Stay near the malecón if you want evenings on foot. Look farther toward Sayulita or the quieter south shore if the point is swimming and slower days. Typical December highs around 85°F are warm without the Caribbean humidity spike.
Best for: West Coast travellers who want beach plus town life on a short Pacific hop.
Los Cabos sits only $2 above Puerto Vallarta from Los Angeles in this snapshot, which makes the choice about mood rather than money. Cabo is drier, more resort-facing and built around the Baja desert meeting the sea.
Typical highs around 75°F are warm winter sun rather than sticky tropical heat. That is a feature if you want outdoor days without melting between the pool and dinner. Check resort pricing carefully: the airfare can look like a gift and still leave you in Cabo hotel territory.
Best for: a polished Baja beach week when dry heat and resort infrastructure matter more than a lively town centre.
Nassau is the shortest mental leap from the Northeast. At $306 from New York, you get a warm island weekend (or week) without a long haul, and the destination works whether you want a resort bubble or a few days exploring New Providence.
Typical highs around 81°F are solid beach weather. The catch is the same as Aruba and Punta Cana: December hotel rates can erase the airfare win if you do not check lodging before you celebrate the ticket.
Best for: a quick warm island trip from New York when travel time matters as much as temperature.
Curaçao is where this list gets more interesting than the obvious beach package. At $348 from New York, you get colour, a walkable centre in Willemstad, and beaches close enough that a five- or six-night trip does not need a complicated island circuit.
Typical highs around 86°F deliver real heat. December can still bring occasional showers in the southern Caribbean, so pack for warm days with a plan B, not for guaranteed perfect beach weather every afternoon.
Best for: travellers who want Dutch Caribbean character plus beach days, not only a resort strip.
Liberia is the airport; Guanacaste is the holiday. At $366 from New York, the fare is low enough to make the Pacific side of Costa Rica feel practical rather than aspirational.
Use Liberia as the gateway to Papagayo for the classic beach stretch, or Rincón de la Vieja if you want volcano and dry forest within reach of the coast. December here is dry-season heat. Typical highs around 90°F are the kind of warmth people are actually looking for when they leave a cold U.S. winter.
Best for: a hot beach week with room for nature, without a complicated itinerary.
Cartagena is the stretch pick if you get bored after four hours on a beach. At $381 from New York, the fare is the highest on this list, but what you buy is a walled city, Caribbean evenings and day trips that feel different from another resort corridor.
The historic centre handles the atmosphere. Nearby islands and beaches handle the swimming. Typical highs around 88°F mean real heat, with evenings that stay warm. This is a city-first warm trip, not a sand-only package.
Best for: a warm city break with Caribbean access when culture matters as much as the beach.
San Juan, Puerto Rico from Chicago at $172 round trip is the lowest fare on this list, followed by Cancún from Chicago at $262.
New York leads six of the ten destinations in this snapshot, mostly across the Caribbean. Chicago wins San Juan and Cancún. Los Angeles wins Puerto Vallarta and Los Cabos.
Guanacaste, Costa Rica leads this list with typical highs around 90°F. Cartagena, Aruba and Curaçao sit in the mid-to-high 80s.
Not usually. Los Cabos is closer to 75°F in December, which is warm winter sun rather than sticky tropical heat. That can be a plus if you want outdoor days without peak humidity.
No. From New York, Aruba, Punta Cana and Nassau sit within a few dollars of each other. Hotel costs, travel time and the kind of trip you want matter more than a $6 gap on the airfare.
Not necessarily. The snapshot uses the cheapest available travel dates within December. Peak holiday weeks can look completely different, so check your exact dates before assuming the table price still applies.