Nonstop Flights From Chicago To The Caribbean

By Leslie Veliz
Punta Cana, Dominican Republic Nick N A/Shutterstock

From its enriching experiences to its extraordinary skyline, Chicago is a city that keeps giving. However, it's one thing to be a tourist in Chicago and another to live there. This is especially true if you detest frigid temperatures. The Windy City has been known to have arctic-like conditions during the winter. For example, in January 2024, the temperature dropped to -10 degrees Fahrenheit. Sadly, residents have to wait until June to encounter sweat-inducing weather. 

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If you live in Chicago and prefer to skirt its frosty climate, travel to the Caribbean on a nonstop flight from O'Hare International Airport (ORD). ORD is considered one of the busiest airports in the world and has several direct flights to different parts of the world. In other words, those departing from Chicago are not limited when it comes to deciding on a Caribbean destination. Airlines like American Airlines and United Airlines offer direct flights to a romantic island of your choice.

There's also Chicago Midway International Airport (MDW). MDW is about 30 minutes from Downtown Chicago, and ORD, which is much larger, is about an hour away. So ditch your coat, scarf, and gloves for a bathing suit and the Caribbean's tropical weather. A stunning island, perfect for experiencing Caribbean culture, is only a few hours away. 

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Trade the Windy City for these Caribbean islands

Saint Lucia Vadim_N/Shutterstock

From O'Hare International Airport (ORD), there are nonstop flights to Puerto Rico's Luis Muñoz Marin International Airport (SJU), Punta Cana Airport (PUJ) in the Dominican Republic, and Sangster International Airport (MBJ) in Montego Bay, Jamaica. Note there are also flights to PUJ and MBJ from Chicago Midway International Airport (MDW).

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Furthermore, travelers can fly directly to the Bahamas from ORD to Nassau's Lynden Pindling International Airport (NAS), Aruba's Queen Beatrix International Airport (AUA) in Oranjestad, and the Cayman Island's Owen Roberts International Airport (GCM).

Additional destinations from ORD include Hewanorra International Airport (UVF) in Saint Lucia (pictured), Cyril E. King Airport (STT) in Saint Thomas, and Princess Juliana International Airport (SXM) in Sint Maarten. 

American Airlines 

  • San Juan, 4 hours, 40 minutes (ORD-SJU) 
  • Punta Cana, 4 hours, 30 minutes (ORD-PUJ)

  • Montego Bay, 4 hours, 4 minutes (ORD-MBJ)

Frontier 

  • Punta Cana, 4 hours, 37 minutes (ORD-PUJ)

Southwest Airlines 

  • Punta Cana, 4 hours, 25 minutes (MDW-PUJ)

  • Montego Bay, 3 hours, 55 minutes (MDW-MBJ)

Spirit 

  • San Juan, 4 hours, 43 minutes (ORD-SJU)

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United Airlines 

  • San Juan, 4 hours, 47-50 minutes (ORD-SJU)

  • Punta Cana, 4 hours, 36 minutes (ORD-PUJ)

  • Nassau, 3 hours, 23 minutes (ORD-NAS)

  • Montego Bay, 4 hours, 4 minutes (ORD-MBJ)

  • Aruba, 5 hours, 14 minutes (ORD-AUA)

  • Cayman Islands, 4 hours, 2 minutes (ORD-GCM)

  • Saint Lucia, 5 hours, 35 minutes (ORD-UVF)

  • Saint Thomas, 4 hours, 59 minutes (ORD-STT)

  • Sint Maarten, 5 hours, 6 minutes (ORD-SXM)

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