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Last Minute Travel Destinations

Last minute travel often comes with a slew of issues - limited availability at the hotel/resort of your choice, higher airfare, tougher dinner reservations, however, patience and choosing your destination wisely can help off-set those problems. Look for destinations with plenty of lodging options - cities and large resort hubs are your best bets - embrace the shoulder season (spring and fall, generally) and avoid the busiest travel times of the year (that can also be destination specific, i.e. cherry blossom season in Tokyo and summer in Italy). Here are a few last-minute ideas for the best destinations to plan last minute trips. 

  1. Louisville, Kentucky: if you're interested in history, culture, and a charming Southern atmosphere, Louisville is a great destination for you (just avoid Derby weekend - first weekend in May if you are going last minute). Watch racing at Churchill Downs, explore the bourbon distilleries along the Bourbon Trail, and savor delicious Southern comfort food dishes like hot browns and fried chicken. 
  2. New York City, New York: With its iconic landmarks, Broadway shows, and diverse neighborhoods, NYC offers endless activities and experiences for travelers. Stay: Whitby Hotel, Crosby Hotel or the Lotte Palace
  3. New Orleans, Louisiana: Experience the lively music scene, unique cuisine, and rich culture of the French Quarter and beyond. (Avoid: Mardi Gras and Jazzfest) Stay: Maison de la Luz 
  4. Miami, Florida: Enjoy the beaches, Art Deco architecture, and vibrant nightlife in this coastal city. Stay: The Miami Beach Edition or Acqualina Miami
  5. San Francisco, California: Explore the Golden Gate Bridge, Alcatraz Island, and the eclectic neighborhoods that make up this iconic city. Stay: The Four Seasons or the Ritz Carlton Half-Moon Bay
  6. Oahu, Hawaii: offers a vibrant and diverse range of experiences that make it an attractive destination for travelers. Explore world-class beaches, a vibrant night life, and spectacular scenery without the crowds of Maui. Stay: Four Seasons Resort Oahu at Ko Olina or Turtle Bay Resort on the North Shore or Espacio on Waikiki.
Photo by C Lissner
  1. Barcelona, Spain: Experience the blend of art, architecture, and Mediterranean charm in this vibrant Spanish city. The Barcelona Edition or The Almanac
  2. Bangkok, Thailand: Enjoy bustling markets, ornate temples, and delicious street food in Thailand's capital. Stay: The Mandarin Oriental or The Siam 
  3. Hong Kong, China: stunning skyline, vibrant culture, and a mix of modernity and tradition, Hong Kong offers a wide range of experiences for travelers. Stay: The Upper House or the Rosewood
  4. Dublin, Ireland: Discover the lively pubs, historic sites, and warm hospitality of the Irish capital. Stay: The Merrion or the Westbury Hotel
  5. Tokyo, Japan: Immerse yourself in a mix of traditional and modern culture, from ancient temples to futuristic technology. Stay: The Palace Hotel, the Park Hyatt or the Aman
  6. Los Cabos, Mexico: Relax on white sandy beaches and enjoy water activities in this popular Mexican resort city. Stay: The Viceroy, the Four Seasons at Costa Palmas or the One & Only Pamilla

Only have a weekend? Check out our list of weekend getaways from Chicago

And check out our list of Fall Destinations for other last minute trip ideas.