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!
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.

Cook Islands - Exclusive $200 OFF per booking offer: Valid on new bookings made 9/24 - 12/2/18 for select travel 9/24/18 - 7/31/19, except for Little Polynesian Resort, which is valid for select travel 4/1 - 7/31/19. Discount is per booking, taken at time of booking and reflected in rates shown. Minimum 5-nights' accommodation at a participating hotel or resort and roundtrip transpacific airfare required. Offer not combinable with all specials and may be changed or withdrawn at any time.
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.

Why you should go: Because nature and mild danger make you feel alive. Victoria Falls has a bungee jump, one of the world’s most high-octane whitewater runs, and the Devil’s Pool, a natural rock pool at the literal edge of the falls. Forget TLC’s admonitions: Inching your body out over the precipice and looking down into one of the seven natural wonders of the world is one of the most unforgettable things you’ll ever do. - Sarah Theeboom, Thrillist contributor


Couchsurfing hosts sometimes take great pride in serving as tour guides and cultural ambassadors for their visitors. The website features quotes from visitors, such as Sam, who said, “Nong showed me the sights and helped me search out the best street eats (insects included!) during my week in Bangkok. She also helped me with more practical matters, like getting my Myanmar visa and planning the next leg of my Thailand trip.”
Why: While the devastating hurricanes of 2017 impacted just a portion of the Caribbean region, it damaged some of its more cruise-popular spots, like Tortola in the British Virgin Islands, St. Martin, Puerto Rico, St. Bart's, and the U.S.V.I.’s St. Thomas, St. Croix and St. John. While all are under significant rehab and rebuilding — and most are actually now open to cruise ships and tourists, this could be a perfect year to explore more exotic islands. That’s because lines like Windstar, which had, pre-hurricanes, planned to offer BVI-centric trips, relocated ships to other parts of the Caribbean. The winning trip? We love Wind Surf, one of the line’s sailing vessels, with its trip out of Barbados; ports include Martinique, Guadeloupe, and Montserrat — all islands that heretofore have often been bypassed by established cruise lines. And get this: There’s plenty of cruise capacity in this region, particularly when it comes to small ship sailings. In part, excess cabins are available because many skittish travelers canceled their bookings. As well, they can typically be more expensive (look for $300 per person, per day) than big ship vessels. But do the math: Windstar, and other small ship lines like Crystal, Regent Seven Seas, Seabourn, Azamara, Oceania and Viking Oceans, can actually be quite a good value when compared to land-based properties because they’re more price inclusive. Look for deals that include cocktails, gratuities and shore excursions not to mention pre- and post-cruise hotel stays and, in some cases, airfare to the ships’ port of embarkation.
Fiji - Exclusive $300 OFF per booking offer: Valid on new bookings made 9/24 - 12/9/18 for select travel 9/24/18 - 7/31/19. Minimum 7-night hotel accommodations at participating hotel, resort or cruise provider and roundtrip transpacific airfare required. Offer not combinable with all specials and may be changed or withdrawn at any time. Savings is per booking, taken at time of booking and reflected in rates shown.
A Dominican Republic favorite known for its high-end resorts, Puerto Plata is also a great place to visit on a budget. The sands of Playa Dorada and Cabarete are perfect for whiling away days amongst heavenly surrounds, while Fort San Felipe del Morro, a 16th century citadel and World Heritage Site, offers the chance to ingest a little history and culture. For value eats, head to Sam's Bar and Grill, and finish the night off with a trip to Mangu for a great night out.
For example, a writer for The New York Times searched for a long weekend getaway in Washington, D.C. and found a vacation package that looked like a tremendous deal. However, the hotel was 22 miles away from Washington. In other scenarios, the hotel might be fantastic, but your flight might have two stops and a 12-hour layover in Topeka. The bottom line is that it’s worth exploring package options, but be sure to scrutinize the individual components of the package to make sure you’re not compromising too much.
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.
CheapOair makes it easy to find and book travel packages at great prices. Now you can save even more by booking your flight, hotel, and car rental together. CheapOair works closely with top travel brands to ensure that you get the best vacation deals possible. We offer cheap vacations & packages to the most sought after destinations around the globe. From all-inclusive vacations to kid friendly destinations, romantic and leisure travel, to name a few.
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