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!

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.

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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.

Travel rewards credit cards are specifically designed to let a user earn points by making purchases and applying those points directly toward flights and hotels. Some travel rewards credit cards, such as the Delta SkyMiles Credit Card from American Express, are limited by affiliation with a specific travel company. If you’re not keen on sticking to one provider, there are others – including the U.S. Bank FlexPerks Visa Cards – that allow you to apply points toward a wider range of travel services. (FlexPerks is affiliated with 150 airlines, as well as many hotels, cruise lines, and rental car companies.)
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: The Central Coast runs roughly from Santa Barbara to Monterey and the string of small towns between San Simeon and Pismo Beach is an unexpected surprise for many California coast road trippers. This is where SoCal surf town meets fishing village, and otters and elephant seals share the spotlight with European masterpieces at the Hearst Castle. Veer away from the coast and in a few minutes you'll find yourself at the wineries of Paso Robles, with tastings that are half the price of Napa and Sonoma. Adelaida is open daily; for a special hilltop tasting, try their Vineyard Tour, Taste and Tailgate. An emphasis on eating local and fresh creates foodie-worthy dining options throughout the region. Pismo Beach and quaint Moonstone Beach in Cambria offer the largest selection of lodging with the best value outside of the holidays and summer. Guests at Cambria Shores Inn relax each evening in Adirondack chairs positioned perfectly to take in the sunset. Afterwards, take a five-minute stroll to Sea Chest Restaurant for local seafood or drive to the Cracked Crab in Pismo Beach where the Deadliest Catch crew dined and all things crab are on the menu.

Choosing the right vacation package has never been easier or more affordable. Check out some of our suggestions in the "Top Vacation Packages", "All Inclusive Deals" or "Last Minute Deals" sections. Whichever selection you choose, you can be sure that CheapOair will get you where you want to go at a price that can't be beat. We're constantly updating our great vacation deals and offers, so be sure to check back with CheapOair often. Now is the time to take advantage of our best deals while they last!
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