*Savings based on all holiday package bookings with Flight + Hotel on CheapTickets.com from July 1, 2015 to June 30, 2016, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.
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!
*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

Why you should go: London is always a winner, but venture north to the Yorkshire Dales to experience the majestic, windswept hills of the Brontë sisters, or take a train south west to the Jurassic cliffs of seaside town West Bay, Dorset (you may recognize them from Broadchurch). Both of these options, much more budget friendly than the capital, offer England at its most beautiful. - Ruthie Darling, Thrillist contributor
Why: Encircled by massive stonewalls, this Adriatic gem is hard to resist. With its old-world charm, the city’s streets are paved with limestone giving it a cool feel during hot summer days. Its well-preserved homes and monuments range from baroque St. Blaise Church to renaissance Sponza Palace and Gothic Rector’s Palace. It’s a perfect day excursion when island hopping along the Adriatic coast. Oh, and you won’t want to miss the stunning medieval fortresses, Lovrijenac and Bokar, which tower over Dubrovnik.

This is Mother Nature at her best. Take a bus to explore 27 mammoth waterfalls as well as emerald Dominican jungle and local wildlife. A guided walking tour of the first seven waterfalls is around $6 (it costs extra if you want to see more of them), or you can spend more to explore them by Jeep. Word to the wise: Bring your bathing suit and bug spray.
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.
When the lure of a tropical paradise beckons, the Caribbean is second to none. Immerse yourself in the laid-back island lifestyle, and enjoy wonderful all-inclusive resorts, fantastic beaches, marvelous diving and snorkeling, challenging golf and great shopping. Whether you are looking for the perfect atmosphere for a romantic getaway or an exciting adventure for the whole family, Caribbean vacations are fun for everyone.  
Chosen By: Emily McNutt, associate editor at The Points Guy, where she is responsible for reporting on travel news across a range of topics — from aviation to loyalty programs, general travel news and credit cards. At TPG, McNutt is not only an expert in the travel and points and miles space in the newsroom, but also puts that expertise to work by reviewing aircraft products for the site. With a lifelong passion for travel, McNutt has visited more than 40 countries.
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Why: This small island nation is easy on the wallet and big on experiences. I came here on a three-week tour expecting to be a beach bum, but instead, found so much more: delicious (albeit spicy) food, stunning ancient rock formations in Sigiriya, surfing at Arugam Bay, and some of the most physically rewarding hikes I’ve ever done. Climbing to the top of Adam’s Peak and (barely) surviving the 5,500 steep stairs that make up this pilgrimage, with the help of a friend and a monk, taught me some inner lessons about strength and power. Don’t miss a chance to visit Ella, a small mountain town with a laid-back hippy vibe, accessible via a scenic train ride from Kandy that will cost you less than $10 and bring you past stunning tea plantations. The real magic of the country is outside of Colombo, but since your flight will always begin/end here, I strongly recommend starting your trip with a stay at Penthouse Above Sea ($100 a night). The amazing woman who runs this property can help you plan your time in the country.

*Unless otherwise noted, fares include ROUNDTRIP AIRFARE via U.S. certified air carrier, hotel transfers (in Mexico and the Caribbean), hotel tax, resort baggage handling, fuel surcharges and all pre-collected U.S. and foreign taxes and fees including September 11th Security Fee. Packages in Turks and Caicos or San Juan, Puerto Rico do not include airport transfers. Packages flying into Cancun but staying in Cozumel require supplemental ferry transfers at an additional cost. More details


Enjoy an all-inclusive vacation from the HotelInn Hotel in sunny Jamaica for 5 nights and book a 40% discounted getaway to Montego Bay, home of idyllic beaches, deep seas, good vibes, and lush jungles. What's Included? Based on two people sharing, this vacation deal includes round-trip flights, an all-inclusive 5-night stay at the 3.5-star Holiday…
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