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!

Why you should go: Don’t let the name fool you; Isla Grande is an intimate, gorgeous Caribbean island just a 45-minute boat ride from Cartagena, full of exceedingly friendly locals and all the hallmarks of a tiny paradise. You’ve got your idyllic beaches, your lagoons of bioluminescent plankton that turn the water bright blue, your fresh seafood and multiple options for diving and canoeing. The chance to visit such a place is probably why you bother to earn money in the first place. - Daniel Cole, Thrillist contributor
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Why: For an affordable and sun-soaked vacation, southern Portugal’s Algarve region should be hot on your radar. The city of Albufeira boasts a beautiful climate, fabulous beaches, inexpensive apartment-style hotels and a central location within the Algarve. There are over 100 different restaurants, bars and nightclubs, and Albufeira even has a charming Old Town with traditional Portuguese streets and plazas within the city center. The prices for both food and wine are extremely reasonable; be sure to sample the wines of Portugal. While summer remains the busiest and most popular time to visit, I love visiting in late spring — the weather is pleasant and sunny, there are fewer tourists and hotel rates are very affordable. Albufeira also offers easy access to nearby towns such as Loulé, with its famous market and an authentic slice of Portuguese culture. Rent a car to see the church of São Lourenço in Almancil, famous for its exquisite blue tile. Head north of Lagos to see Ponta da Piedade, with its towering red rock formations against the sea. Play a round of golf in one of the many beautiful courses in the Algarve. The place to stay: the Epic Sana Algarve overlooking Praia da Falésia, where you can bask in the sun at one of its five outdoor pools and indulge at the beautiful spa.
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.
Why you should go: With some 6,000 islands, Greece is the Mediterranean’s powerhouse beach destination. While only 200-some are inhabited, an island-trotting adventure for everyone here, whether you’re looking for wildlife adventures, historic discoveries, or quite frankly, drinking ouzo and boogying. Athens makes an energetic springboard into the Aegean, with its own archaeological ruins, hipster cafés, and hangouts ranging from dynamic industrial to retro chic.

Why you should go: Prague is quintessentially European, an architecture junkie’s dream for its lofty spires, stuccoed high ceilings, and Art Nouveau quirks. Sure, it’s touristy -- just try fighting through the selfie sticks on Charles Bridge or not wincing in disgust at Kafka bastardized on T-shirts and coffee mugs -- but this is also a city with plenty of nooks and crannies to escape from the masses, from dimly lit bars, minuscule art galleries, or in some old world cafe.
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