What makes a destination a good winter beach getaway from Chicago and other Midwest locations? In my opinion, it’s price, proximity to your departure city, and typical weather at the destination during that time of year. Actually, these are my criteria for all winter getaways, not just beach vacations.
Top 5 Winter Getaways from Chicago and other Midwest Locations
Caribbean Cruise from Miami, FL
United, Frontier, and American fly nonstop from Chicago to Miami. Flights are approximately 3 hours. Your options when choosing to cruise the Caribbean from Miami are extensive.
- Carnival, Royal Caribbean, and Norwegian Cruise Line have 3 night Bahamas cruises.
- Norwegian Cruise Line, Royal Caribbean, Disney Cruise Line, and Carnival have 4 night cruises to the Bahamas.
- Carnival has a 4 night Western Caribbean cruise.
- Carnival, Celebrity Cruises, and Disney Cruise Line have 5 night cruises to the Caribbean.
- Carnival has a 6 night Western Caribbean cruise.
- Celebrity Cruises, Carnival, Norwegian Cruise Line, MSC Cruises, and Crystal Cruises offer 7 night Caribbean cruises.
- Carnival has 8 night Caribbean cruises.
- Celebrity has a 9 night Southern Caribbean cruise.
- Oceania has four 10 night Caribbean cruises: the “Island Paradise Cruise,” the “Sands and Shores Cruise,” the “Sun Kissed Sanctuaries Cruise,” and the “Mayan Mystique Cruise.”
- Regent also has a 10 night Caribbean cruise departing from Miami.
- Norwegian Cruise Lines offers an 11 night cruise to the Panama Canal that includes many Caribbean ports of call.
- Azamara and Oceania have 12 night Caribbean cruises.
- Princess Cruises and Crystal Cruises offer 14 night Caribbean cruises.
Riviera Maya, Mexico
United, American, and Southwest fly nonstop from Chicago to Cancun in slightly less than 4 hours. Just 50 miles south of Cancun, Riviera Maya has a quieter, more laid back vibe with just as many things to do, many of them beach and ocean oriented. The area is also known for its all-inclusive luxury resorts.
United flies nonstop from Chicago to Aruba in 5 hours, 10 minutes. Aruba is one of the Caribbean’s most visited islands due to its miles of gorgeous beaches, many lodging options, casinos, and its proximity to the Midwest, Southeast, and East Coast. There’s more to Aruba than sun worshipping tourists though. The farther you travel from Aruba’s main town, Oranjestad, and the beachfront resorts, the more visible Aruba’s natural beauty becomes.
American flies nonstop from Chicago to Montego Bay in 4 hours. Jamaica offers something different than many Caribbean islands. Yes, it has miles of beaches, resorts, and all the activities you’d expect from a tropical island retreat. But, Jamaica also has deep musical roots based in the folk songs of West Africa, and more recently in reggae; lush mountains and inland rivers to be explored; and more than one city/cultural center (In fact, Jamaica has 8: Kingston, Portmore, Spanish Town, Mandeville, Ocho Ríos, Port Antonio, Negril, and Montego Bay.).
St. Martin/St. Maarten
United flies nonstop from Chicago to St. Martin/St. Maarten in 5 hours. Fodor’s describes St. Martin/St. Maarten in this way:
“French and Dutch have lived side by side on St. Maarten/St. Martin for hundreds of years—with no border patrols or customs between them. The French side has a more genteel ambience, more fashionable shopping, and a Continental flair. The Dutch tends to be less expensive, has casino hotels, and more nightlife.” One thing that both the French and Dutch sides of the island share are outstanding opportunities to engage in a variety of watersports including scuba diving, snorkeling, sailing, and windsurfing,
To many joyful beach experiences!
— Lisa Dworkin