While hotel prices might be cheaper in underrated locales, you do need to be aware that flight prices might be more expensive – and possibly at less convenient times with more stops – if it’s not a common route. For example, an August flight from Minneapolis to Rio de Janeiro, Brazil might cost around $857, but a flight at the same time from Minneapolis to La Paz, Bolivia costs $1,177. The distance is nearly identical, though most flights to La Paz require at least two (and, in many cases, three) stops, whereas there are flights available from Minneapolis to Rio de Janeiro with only one stop.

Caribbean - Last-Minute Holiday Sale offer: Valid on new bookings at participating resorts made 10/29 - 11/25/18 for select travel 10/29/18 - 1/5/19. Offers vary by hotel and may be category-specific, require advance booking, be restricted to specific days of the week and/or require a minimum night stay. Booking and travel dates vary by hotel. Blackout dates may apply.
Why you should go: For all the greedy reasons: Its landscape varies from world-famous Pacific surf beaches to strikingly beautiful inland mountains, you’ll eat the best Mexican food you’ll ever have, the city is packed with pure magic. And for a selfless one: After a brutal past year of political rhetoric in the States, now is a great time to show our neighbors to the south some love. Whatever scant bucks you spend will boost their economy and help preserve the many indigenous cultures that call Oaxaca home. - Tess Rose Lampert, Thrillist contributor
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!

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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