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Created at April 26, 2019

Vacations under 5 hours flight

The best vacations are the ones where you don't spend all day in a plane. Quick flights from the city get you to exotic destinations. Find out which ones and add your recommendations to the list!

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Cayman Islands
Cayman Islands
4.7
(3)
Cayman Islands
Rate
It is under 4 hours from Chicago. The Caymans are three islands, each with a different vibe. On a short trip, you’ll get the most out of your time on Grand Cayman, the largest. Visit the Cayman Turtle Centre to swim with sea turtles (and learn about local marine life).
Mount Rainier National Park
Mount Rainier National Park
4.7
(3)
Washington, USA
Rate
Easily one of the most picturesque landscapes in Washington state, if not all of the United States of America, no visit to Seattle would be complete without a jaunt to Mount Rainier.
Las Vegas
Las Vegas
4.7
(3)
Las Vegas, NV
Rate
I’m single
Grand Cayman
Grand Cayman
4.7
(3)
Grand Cayman, Cayman Islands
Rate
If the words Seven Mile Beach don’t mean anything to you, it’s time to get acquainted with one of the Caribbean’s greatest hits. Other attractions like Eden Rock and Devil’s Grotto make it absolutely clear (no pun intended) why these breathtaking beaches are easily worth the three-and-a-half-hour flight.
Montego Bay
Montego Bay
4.7
(3)
Montego Bay, Jamaica
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Get in the island spirit in Jamaica, where there's something for everyone. Whether you want to relax with rum punch or let loose in the Caribbean sun, it's easy to hop on a short four-hour flight and land right in the heart of reggae music and jerk chicken. Spend an hour or two touring the haunted Rose Hall estate, or take a day trip to Ocho Rios, where you can climb the waterfalls at Dunn’s River Falls or go bobsledding through the forest.
Azores
Azores
4.5
(2)
Azores, Portugal
Rate
The remote islands of the Azores in the North Atlantic belong to Portugal, but their rugged, wind-swept and verdant good looks appear to be a mix of New Zealand and Hawaii. You’re in a very exotic corner of the world here, and 4 hour flights from Boston make it surprisingly easy to get to the Azores. Intrepid families who love hiking and whale-spotting and don’t mind chilly ocean waters will have it made exploring the archipelago. Islands hardly get more exotic than the Azores.
Lake Louise
Lake Louise
4.5
(2)
Lake Louise, AB
Rate
You can fly into Calgary in about four hours from Chicago. Look for tickets in the $300 range.Situated in the Banff National Park, the glacier-fed Lake Louise is where, from December-ish to April-ish, you can avail yourself of what many consider to be the world’s best ice-skating rink -- go after dark for night skating. In the summer, go rock-climbing or horseback riding, and if you have the extra coin there’s heli-hiking.
Bermuda
Bermuda
4.5
(2)
Bermuda
Rate
It's a short nonstop flight from Boston and families love to go biking together on the Bermuda Railway Trail that covers the island from end to end, and the Crystal Caves are fascinating to explore. Don’t miss the postcard-perfect beach at Horseshoe Bay, with its sand particles colored the same hue as cotton candy. For stay, Fairmont Southampton is one of the many family friendly resorts on the island.
Turks and Caicos Islands
Turks and Caicos Islands
4.5
(2)
TKCA 1ZZ, Turks and Caicos Islands
Rate
From Chicago, The flight is less than four hours. You should be able to get a round-trip ticket for comfortably under $500. Keep an eye on Southwest Airlines, which often features discounts to Caribbean destinations. As activities go, there’s a beach full of puppies you can play with, so that’s a start. A massive barrier reef makes the waters ideal for swimming and snorkeling.
St Lucia
St Lucia
4.5
(2)
St Lucia
Rate
If you've been itching to travel to Honolulu but dread the 13-hour flight, Then just 4 hours and 30 mins away is Saint Lucia, the Caribbean cousin of Hawaii. You'll be able to indulge in glorious scenes of the island's lush greenery, volcanic mountains, and a dazzling array of activities. Ideal for nature lovers, there are plenty of hikes where you can glimpse sweeping views, an underwater marine park where you can go scuba diving, and crystal clear waters perfect for kayaking