Why: Following the devastation caused by Hurricane Maria, travelers might be reluctant to visit the territory of Puerto Rico. But, on a recent visit to the island to help rebuild some of the most popular tourist attractions, I was thrilled to see that Puerto Rico is thriving and really is open for business. If you don’t have a passport — or if you have one that’s closed to expiring or being filled — one of the best parts about visiting Puerto Rico is that no passport is needed for U.S. citizens. With plenty to see both in San Juan — from the charm and bright colors of Old San Juan to checking out where one of the most famous rums in the world is made at the Bacardi Factory ($15 for a historical tour) — and outside, such as a trip to El Yunque National Forest, you'll be kept busy. Flights to San Juan generally will run you less than $250 from the East Coast, making it a perfectly close and affordable getaway. While there are several affordable chain hotels, boutique hotels flourish — especially in Old San Juan. Check out The Gallery Inn or Decanter Hotel.
Why: Following the devastation caused by Hurricane Maria, travelers might be reluctant to visit the territory of Puerto Rico. But, on a recent visit to the island to help rebuild some of the most popular tourist attractions, I was thrilled to see that Puerto Rico is thriving and really is open for business. If you don’t have a passport — or if you have one that’s closed to expiring or being filled — one of the best parts about visiting Puerto Rico is that no passport is needed for U.S. citizens. With plenty to see both in San Juan — from the charm and bright colors of Old San Juan to checking out where one of the most famous rums in the world is made at the Bacardi Factory ($15 for a historical tour) — and outside, such as a trip to El Yunque National Forest, you'll be kept busy. Flights to San Juan generally will run you less than $250 from the East Coast, making it a perfectly close and affordable getaway. While there are several affordable chain hotels, boutique hotels flourish — especially in Old San Juan. Check out The Gallery Inn or Decanter Hotel.

Why you should go: Too few Eurotrips include Poland, despite its sharing borders with Germany and the Czech Republic. Warsaw is a hotbed of glamor and flash, while Kraków is the epitome of charming hipster enclaves, but the truth is that both of these cities are of crucial historical importance -- and what happened here should never be forgotten. Millions of Poles died or fled during the Nazi invasion. Warsaw was basically burned to the ground. The country’s long history is rich and fascinating, set in what is today a peaceful and beautifully scenic land.
Chosen By: Amie O’Shaughnessy, founder and CEO of Ciao Bambino. After having her son, Amie searched extensively for credible resources to provide family-focused advice, direction and useful accommodation information. She quickly realized that there were no relevant resources available, particularly for a discerning traveler, so she decided to help solve this problem and started Ciao Bambino.
Hotel Tonight. While Hotel Tonight is an app that bypasses direct communication with travel companies, it can still be a great source for good, last-minute deals. Hotel Tonight takes advantage of hotel owners’ desire to fill empty rooms by enabling last-minute bookings at up to 70% off standard rates. It’s available for iPhones, iPads, and Android devices.
Two of the higher-quality San Francisco options in which you can enjoy some of the best hotel features in town, are the Fairmont Heritage Place, Ghirardelli Square, at 900 N Point Street, and The St. Regis San Francisco, at 125 3rd St. Alternatively, The Wharf Inn, at 2601 Mason St, and the Layne Hotel, at 545 Jones St, are a couple of accommodations worth checking out if you are a bit more budget conscious.
If you’re tempted to make a vacation-related purchase but are a little put off by the price tag, add the item to your electronic cart – but don’t go all the way through with the purchase. Before doing this, be very careful to make sure that it’s not a one-click purchase or a website where your payment details are stored, or anything else that will rope you into a purchase that you’re not ready to make.
Just how cheap is it? If you get yourself to Isla Grande -- part of the Islas del Rosario just off the country’s north coast -- it’s a tropical paradise for as cheap as you care to make it. Although there are fancier resorts available, at eco-hotels such as La Cocotera, Las Palmeras, or El Hamaquero, you can sleep in a beachside hammock for just $10 a night. For $20, you’ll also get you three meals, including a freshly caught and grilled fish dinner. Or, pro tip: A local can bring you freshly caught lobsters on request from anywhere between $10 to $30 a day. Sneak into the upmarket Hotel Majagua and grab a piña colada for $5, or go to the inland village for cut-price cervezas. (If you want more privacy, lodging starts at around $30 per room, and goes up to between $90 to $250.)

Just how cheap is it? The food and accommodation aren’t fabulous bargains -- but, oh, the shopping is. In the tourist town of Victoria Falls, a hostel bed or a hired tent will cost you $15 to $20 per night, but I scored a carved stone necklace from a street vendor for the sandals I was wearing. Bartering is common at flea markets and on the streets, where second-hand clothes -- shoes, baseball caps, and sportswear (think basketball or soccer shirts) -- have real buying power. Fill your suitcase with gently used gear and exchange it for jewelry, handmade crafts, and souvenirs like devalued trillion dollar notes.
Oahu, known as "The Gathering Place," is the most populated area in the island chain. It's also home to some of the most recognizable landmarks in the world like Diamond Head, the world-famous Waikiki Beach, and Pearl Harbor. Most people think of Honolulu, Oahu's largest city and state capitol, as a metropolitan with global flavor, but just a few miles outside of the city limits, quieter getaways can be found. Read more about Oahu
Oahu, known as "The Gathering Place," is the most populated area in the island chain. It's also home to some of the most recognizable landmarks in the world like Diamond Head, the world-famous Waikiki Beach, and Pearl Harbor. Most people think of Honolulu, Oahu's largest city and state capitol, as a metropolitan with global flavor, but just a few miles outside of the city limits, quieter getaways can be found. Read more about Oahu
If you’re looking for a deep-dish pizza, world-class hockey, or a walk through Millennium Park, we can help you see—and eat—it all with a Chicago vacation package. There’s always something to do here in the crown jewel of Illinois, from a walk on Navy Pier to the gorgeous boutiques on the Magnificent Mile. Pardon our pun, but we’re sure “The Windy City” will “blow” you away!
Hotel Tonight. While Hotel Tonight is an app that bypasses direct communication with travel companies, it can still be a great source for good, last-minute deals. Hotel Tonight takes advantage of hotel owners’ desire to fill empty rooms by enabling last-minute bookings at up to 70% off standard rates. It’s available for iPhones, iPads, and Android devices.

After a long winter, spring break tempts millions away from their homes in favor of sunny destinations and fruity drinks with umbrellas in them. Unfortunately, that mass exodus creates demand that drives up both flight and hotel prices. Even if you’re staying within the continental United States, expect to share a plane with spring breakers on the first leg of their international trips – and expect to pay accordingly.
Why you should go: The landlocked country has a rich indigenous culture (por ejemplo: you can buy dried llama fetuses from colorfully dressed mamitas in the markets of La Paz), and a stunning range of landscapes, from rust-colored desert where dinosaurs once trekked to lush pampas and jungles to the otherworldly expanse of the Salar de Uyuni, where the horizon disappears between ground and sky. Adventurous spirits can find some of the cheapest paragliding in the world in Cochabamba, while mountaineers can tackle the 21,000ft high Nevado Sajama. The rest of us can wander around charming cities like Sucre, or take in the mesmerizing sunsets of Lake Titicaca, as beautiful to behold as it is fun to say. - Laura Yan, Thrillist contributor
Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on Orbitz.com of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.
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