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!
It’s worth noting that if the original price isn’t always posted for these types of deals, so you may not know exactly how much you’re saving (or if you’re saving at all). And while Groupon does post the percent savings (and it’s often 50% off or even higher), some critics point out that the “original” prices for Groupon deals and other discount sites are occasionally inflated to make the deals look better.

Why: Traveling through Central Asia is, in many ways, the ultimate adventure. The infrastructure, though slowly modernizing, isn’t quite there yet, but the scenery and culture are unmatched. I loved every minute of Uzbekistan—the blend of Persian and Soviet influence, the culture, the food, the magnificently preserved religious sites in Samarkand and Bukhara, sleeping in a yurt camp under the stars — it all made for an experience I’ll never forget. Uzbekistan is also fantastically affordable, after you’ve paid the visa fee ($160 for United States citizens). Most hotel stays are under $100, save for the brand-new Hyatt Regency Tashkent (roughly $240 a night), which is worth the splurge. I highly recommend using a company like Kalpak Travel to help you book your trip, as independent travel can be a bit tricky in Uzbekistan and they’re experts in this region.


Why: Moab, Utah is a great place to travel to if you are looking to explore the outdoors. There are two national parks in this town — Canyonlands National Park and Arches National Park, along with state parks and lots of recreational land all over. You can camp for free in many different areas around town, or there are also hotels and Airbnbs. If you like to camp, then like I said, you can camp for free in a beautiful place with a mountain or canyon view. An affordable way to see Moab is to stay in one of its many cabins. For example, you can stay at Archview RV Park in a basic Camping Cabin with two beds for just $78 a night. In Moab, there is an endless amount of activities. You can go rock climbing, rafting, kayaking, explore the national parks, skydive, off-road (you can rent Jeeps and go off roading if you don't have your own), camp and more. My favorite tour is the river raft trip with Canyon Voyages.

Hotwire’s “Hot Deals.” Much like Priceline, Hotwire is able to offer discounts if you’re willing to book a hotel, flight, or car without knowing the brand name. Unlike Priceline, Hotwire publishes the prices up front instead of allowing you to name your own price. So, for example, you’ll know that you’re booking a three-star hotel in the Brentwood neighborhood of Los Angeles that costs $120 per night, but you won’t know the name of the hotel until after you book.

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.


These deals are different from fare alerts in that they don’t correspond to a locale of your choice – instead, it’s a company-curated list of deals that may include locations all over the country and the world. Signing up for these types of emails is particularly valuable if you aren’t set on a certain destination or time-frame and simply want to go somewhere and get a good deal on the trip.

The East Coast has it all: beautiful beaches, stunning vistas, historical importance, and some of the most famous cities in the world. First stop on your Eastern Seaboard getaway: the “Big Apple.” A trip to New York City means you get to see the sights that are talked about all over the world, like Lady Liberty, Broadway, and Central Park. If you want to delve into U.S. history, a Washington D.C. vacation filled with monuments, museums, and galleries is for you. Speaking of history, the American Revolution got its start in a city a few hours to the north. Your Boston vacation will bring you to one of the most popular spots on the East Coast. Indulge in some of the best clam chowder in the world, then walk back in time on the Freedom Trail, which hosts 16 sites that played a huge role in the founding of the nation.
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.
Just how cheap is it? The food and accommodation aren’t fabulous bargains -- but, oh, the shopping is. In the tourist town of Victoria Falls, a hostel bed or a hired tent will cost you $15 to $20 per night, but I scored a carved stone necklace from a street vendor for the sandals I was wearing. Bartering is common at flea markets and on the streets, where second-hand clothes -- shoes, baseball caps, and sportswear (think basketball or soccer shirts) -- have real buying power. Fill your suitcase with gently used gear and exchange it for jewelry, handmade crafts, and souvenirs like devalued trillion dollar notes.
Switch up the usual Caribbean getaway this winter and check out gorgeous Cartagena, Columbia. You'll find white sand beaches, plus a beautiful old city and vibrant culture. Your 4-star hotel is only steps from Bocagrande Beach and just five minutes away from historical downtown Cartagena. What's Included? Based on two people sharing, this vacation deal…
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