February fares from New York, Chicago, Dallas and Los Angeles show that real tropical heat can still be surprisingly affordable in the middle of winter.
Round-trip economy fares in U.S. dollars from New York, Chicago, Dallas and Los Angeles. Snapshot checked September 26, 2026.
February is exactly when warm-weather flights are supposed to get expensive. Winter has dragged on, the Caribbean is in high season, and a beach starts to sound less like a luxury and more like a reasonable life decision.
But the airfare was better than I expected. Eight of the ten destinations below dropped below $350 round trip from at least one origin, and every destination had a fare under $415. The bigger lesson is that where you start matters almost as much as where you go.
| Destination | New York | Chicago | Dallas | Los Angeles | Feb high |
|---|---|---|---|---|---|
| San Juan, Puerto Rico | $344 | $202 | $277 | $337 | ~84°F |
| Cancún, Mexico | $347 | $293 | $268 | $293 | ~82°F |
| Punta Cana, Dominican Republic | $287 | $311 | $472 | $485 | ~84°F |
| Puerto Vallarta, Mexico | $338 | $304 | $319 | $304 | ~85°F |
| Los Cabos, Mexico | $372 | $308 | $359 | $308 | ~75°F |
| Aruba | $312 | $496 | $571 | $432 | ~82°F |
| Guanacaste, Costa Rica | $325 | $489 | $573 | $417 | ~90°F |
| Montego Bay, Jamaica | $347 | $370 | $483 | $472 | ~84°F |
| Willemstad, Curaçao | $398 | $621 | $721 | $530 | ~86°F |
| Cartagena, Colombia | $425 | $411 | $594 | $429 | ~87°F |
San Juan keeps doing something unusual in these fare snapshots: it behaves more like a cheap domestic trip than a Caribbean escape.
From Chicago, the lowest February fare came in at $202 round trip. Dallas was $277, while New York and Los Angeles were both in the mid-$300s.
The weather is not a compromise. February days in San Juan typically reach the mid-80s, and this is one of the drier parts of Puerto Rico's year. For U.S. citizens, there is also no passport requirement for travel between the mainland and Puerto Rico.
What makes San Juan especially useful is that the trip still works when you are tired of the beach. Old San Juan, the forts, bars, restaurants and neighborhoods give you enough city around the water to fill several days without inventing activities.
Best for: the cheapest tropical February escape, especially from Chicago.
Cancún is the most evenly useful fare in this list.
Dallas came in at $268 round trip, while Chicago and Los Angeles were both $293. Even New York at $347 is still reasonable for February.
The weather is also easy to understand. February is warm rather than brutally hot, rainfall is relatively low, and daytime temperatures sit around the low 80s. That makes beach days comfortable without the humidity of late summer.
More importantly, Cancún gives you options after the flight is booked. You can stay in the Hotel Zone, move south toward Playa del Carmen, take the ferry to Isla Mujeres or spend part of the trip inland around Valladolid.
And because the accommodation market is so large, a cheap flight is less likely to be destroyed by the first hotel search.
Best for: the easiest warm February trip to keep within a real budget.
Punta Cana is excellent from the Northeast and much less interesting from the western half of the country.
New York was $287 round trip, Chicago $311. Dallas and Los Angeles were both close to $500.
February itself is exactly when Punta Cana makes sense. It sits inside the Dominican Republic's drier winter period, daytime temperatures are around the mid-80s, and the destination is built around making a beach vacation easy.
That simplicity is either the reason to come or the reason not to.
If you want a resort, warm water, a pool and very few logistical decisions, Punta Cana does that extremely well. If you want to wander through neighborhoods and improvise the trip as you go, there are better choices in this article.
Best for: East Coast travelers who want a straightforward tropical resort week.
Puerto Vallarta is the most balanced destination in the table.
Chicago and Los Angeles were tied at $304 round trip, Dallas was $319 and New York $338. There is no origin here where the airfare suddenly becomes unreasonable.
February is also one of the easiest months to like Puerto Vallarta. The rainy season is long gone, winter days stay in the mid-80s, and evenings are comfortable enough to spend outside.
The city itself matters too. The Malecón, Zona Romántica, restaurants and neighborhoods mean you can build a week that includes the beach without making the beach the entire point.
That is why Puerto Vallarta keeps surviving these lists even when another destination is $20 cheaper.
Best for: the most consistently good February option across all four U.S. origins.
Los Cabos is the one destination here where I would be careful with the word "hot."
It is sunny. It is pleasant. It is warmer than most of the United States in February.
But daytime temperatures around the mid-70s are not the same experience as Curaçao or Costa Rica.
From Chicago and Los Angeles, the fare was $308 round trip, which makes the trade-off much easier to accept. February also sits inside Baja California Sur's winter whale season, and the milder temperatures are excellent for hiking, golf and spending long days outside.
Hotels are where Cabo can become expensive quickly, so I would check the room before getting too excited about the airfare.
Best for: winter sunshine and outdoor weather, especially from Chicago or the West Coast.
Aruba is one of the strongest weather choices and one of the weakest examples of national pricing.
From New York, the fare was $312 round trip.
From Dallas, it was $571.
That difference is the whole reason these articles compare multiple origins instead of pretending there is one national airfare.
February is an excellent time to be in Aruba. The island averages around 82°F, rainfall is low, and brief showers tend to move through quickly. The trade winds also make the heat more comfortable than the number suggests.
Eagle Beach and Palm Beach handle the obvious version of the trip. Arikok National Park and the rougher east coast make renting a car worthwhile if you want to see something beyond the hotel strip.
Best for: New York travelers who prioritize reliable February beach weather.
Guanacaste is where you go if the phrase "winter sun" sounds too mild.
February is deep inside the Pacific dry season, and daytime temperatures around Liberia can reach roughly 90°F. Costa Rica's tourism authority specifically places Guanacaste's dry season from December through March.
New York was the clear winner at $325 round trip. Los Angeles was still workable at $417, while Chicago and Dallas moved into a much less attractive range.
As always, Liberia is the gateway rather than the whole trip. Tamarindo, Papagayo, Playa Conchal and Playa Hermosa take care of the coast, while Rincón de la Vieja gives you volcano trails and hot springs inland.
Best for: the hottest February option and the strongest beach-plus-nature trip.
Montego Bay sits in the middle of the table rather than winning anything outright.
That is not necessarily a weakness.
New York came in at $347 round trip, with Chicago close behind at $370. February sits inside Jamaica's drier December-to-April period, and the weather stays properly tropical.
The bigger question is what kind of Jamaica trip you want.
You can stay in Montego Bay and make this a resort vacation, head west toward Negril for a more beach-focused week, or use part of the trip to see more of the north coast.
Accommodation is still the variable I would check first. A $347 airfare can look very different once the resort total appears.
Best for: Caribbean heat with plenty of accommodation and trip-style choices.
Curaçao makes perhaps the strongest weather argument in the entire article.
February marks the beginning of the island's driest stretch, and temperatures remain firmly tropical. Rainfall is low, trade winds keep the air moving and the weather is much less of a planning variable than on many Caribbean islands.
The airfare, however, is very origin-specific.
New York came in at $398 round trip. Chicago was above $600 and Dallas above $700.
If New York is your airport, Willemstad gives you something many resort destinations do not: a city worth spending time in. The waterfront, restaurants and neighborhoods break up the beach days, while the western side of the island has the smaller coves and swimming spots.
Best for: New York travelers who want dry tropical weather and a Caribbean trip with a real city.
Cartagena is the least beach-first destination in the top ten.
That is why I would keep it.
Chicago had the lowest fare at $411 round trip, with New York and Los Angeles only slightly higher. Dallas was the outlier at $594.
February is hot, with daytime temperatures in the upper 80s, and the Caribbean coast is typically in a drier part of the year. But the reason to fly here is the city.
The walled center, Getsemaní, restaurants, plazas and nightlife can carry most of the trip without needing a resort. Beaches and islands are available when you want them rather than dictating the whole itinerary.
For someone who wants warmth without spending seven days staring at the same stretch of sand, that distinction matters.
Best for: tropical weather, food and city life rather than a resort-first vacation.
Once several flights sit between $300 and $350, I would stop optimizing for the last $20. February hotel prices, weather and the kind of trip you actually want will matter far more.
San Juan was the cheapest fare in the snapshot at $202 round trip from Chicago. Dallas was $277, while New York and Los Angeles were in the mid-$300s.
San Juan, Cancún, Punta Cana, Puerto Vallarta, Los Cabos, Aruba, Guanacaste and Montego Bay all had at least one fare below $350 from one of the four origins.
Guanacaste is the hottest option in this comparison at around 90°F. Cartagena, Curaçao, San Juan and Punta Cana are also firmly tropical.
Cancún was $293, Puerto Vallarta $304 and Los Cabos $308. Those three are especially competitive from Los Angeles.
Curaçao is particularly strong. February begins its driest period, while Aruba and Guanacaste are also excellent choices for low-rainfall winter weather.
Yes, particularly in Guanacaste and along the Pacific side. February is in the dry season, making it well suited to beaches, hiking and other outdoor travel.