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: 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.
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Here's the deal—we've paired budget flights with a top-rated apartment rental in beautiful Aguadilla, Puerto Rico to create a Caribbean getaway for under $260 each! Your apartment is located just minutes from Crash Boat Beach, hiking trails, restaurants, and more. This is the perfect opportunity to escape winter without breaking the bank. What's Included? Based…
Why: A genuine bucket list trip for many, a visit to Australia and New Zealand can be super-pricey. Cities are spread out, way out, which means a lot of hopping on planes to get from one place to another. And for top level accommodations, not to mention simple daily necessities like a flat white, you’ll shell out big bucks. What’s good about a cruise itinerary that includes visits to both countries is that the big expenses are included in fares – onboard meals, accommodations, entertainment and transportation from place to place. On Oceania Cruises, which offers a New Zealand/Australia itinerary, for instance, the per diem is $350 a night, but you pretty much don’t have to whip out a credit card beyond that (do note that it’s priced at per-person, based on two sharing a cabin). Consider that in super-expensive cities like Auckland and Sydney, a hotel stay at a four-star place like the Hilton and Westin respectively will run you $350 or so. And that’s for the room only — you’ll pay out of pocket for food, entertainment and bars. One tip: Look for a cruise line that arranges its itineraries to spend maximum time in port, whether it’s long days or plenty of overnights, so you can have as much time to explore as possible. As well, you’re better off, in most cases, avoiding cruise-line shore excursions, which can be overpriced and epitomize group cattle travel, and engage a travel agency specialist in the region to plan private tours for your days in port. Bottom line, though, is when experiencing Australia and New Zealand by cruise ship, especially on your first visit to the region, the biggest plus is not just the convenience of unpacking once and keeping short-hop plane trips to a minimum. It’s also that, depending on the itinerary you choose, you can visit some pretty special somewhat off-the-grid places in between marquee stops at Auckland and Sydney. New Zealand’s Akaroa, Dunedin and Wellington, and Australia’s Eden, Burnie and Melbourne, might otherwise be missed — and shouldn’t be.

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.
How cheap is it? The UK saying “laters” to the EU may be bad news for Brits, but it’s proving to be great news for travelers. Brexit tied a brick to the already-sinking pound; overall it’s down 30 percent against the dollar since summer of 2014. Airfares, too, have dropped. And the UK is, for the next couple of years at least, formally in Europe -- so super cheap air and train fares that currently operate between the UK and the continent still run post-Brexit, pre-exit. You can be in Paris in 2.5 hours by train. Boom! Take that European trip you’ve been dreaming about since your student days, as it may never be cheaper.
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Why: With so much to see in Namibia, Windhoek, the country’s capital, is just the jumping point. Best of all, the U.S. dollar is strong enough to make travel, accommodations and activities all relatively inexpensive in the country — even for some luxury experiences. Windhoek is cheap in itself and has plenty of see, between exploring the local scenes like at the Namibia Craft Centre and checking out the city's German influence like at the Christuskirche church. Five-star properties, such as the Hilton Windhoek and The Olive Exclusive All-Suite Hotel can be booked for less than $150 per night, thanks in large part to the preferable exchange rate to Namibian dollars. But some of the best sights to see are located outside the city limits. Consider day or multi-day trips to get your outdoor fix and to see the stunning scenery and dunes that makes up the majority of the country. Tours, which often include meals, camping, activities and more, can be found for reasonable prices. If you’re more interested in seeing the beautiful country on your own, consider renting a car and driving to all of the sights. Entrance fees to national parks, such as the Etosha National Park, go for as little as $6 per day. Throughout the country, don’t anticipate spending a lot on food — you can find good, local dining for less than $10 per meal.
Two of the higher-quality San Francisco options in which you can enjoy some of the best hotel features in town, are the Fairmont Heritage Place, Ghirardelli Square, at 900 N Point Street, and The St. Regis San Francisco, at 125 3rd St. Alternatively, The Wharf Inn, at 2601 Mason St, and the Layne Hotel, at 545 Jones St, are a couple of accommodations worth checking out if you are a bit more budget conscious.
Why: As the gateway city to celebrated tourist destinations like the Amalfi Coast, Capri and Pompeii, Naples is finally getting its well-deserved time in the spotlight and intrepid travelers are flocking to the stunning southern city in droves. Naples is one of the oldest cities on the European continent and filled to the brim with intriguing cultural sights and monuments, from seaside castles and underground catacombs to show-stopping Baroque architecture and a plethora of contemporary art. It also boasts one of Italy's most cherished cuisines and is well-known as the birthplace of pizza, which you can enjoy for as little as €4 ($5), accompanied by views of the Bay of Naples and Mount Vesuvius (free). Neapolitan pizza making has just been recognized by UNESCO as part of its Intangible World Heritage list, so now is a great time to visit and enjoy its effervescent energy and fabulous cuisine.
Just how cheap is it? Bulgaria’s capital Sofia is the girls’ getaway paradise you never knew existed, where full-body waxes run about $20 and the full-meal deal of manis, pedis, and haircuts are much cheaper (because Bulgarian women like looking on fleek). A three-course dinner plus vino also shouldn’t cost more than $20 (and the local cuisine here is known to be hearty). Despite its post-Communist exterior, Sofia is also incredibly modern, and you’ll be able to find international bites from tapas to sushi.
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.
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.
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.
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