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!

When the lure of a tropical paradise beckons, the Caribbean is second to none. Immerse yourself in the laid-back island lifestyle, and enjoy wonderful all-inclusive resorts, fantastic beaches, marvelous diving and snorkeling, challenging golf and great shopping. Whether you are looking for the perfect atmosphere for a romantic getaway or an exciting adventure for the whole family, Caribbean vacations are fun for everyone.  
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.

* This is the largest savings for simultaneous booking of flight and hotel from July 1, 2015 to June 30, 2016, and not the discount rate or amount for your booking. Savings calculated based on the cost of a Flight + Hotel booking on Travelocity.com as compared to the aggregated price of the full published fare given by the airline and the cost of your hotel for the same travel products for the same travel dates when made separately. Savings will vary based on the origin/destination, length of trip, stay dates and selected travel supplier(s). Savings are not available on all packages. Please confirm the actual discount rate/ price on the booking page.


Why: Canada, eh? The good news is, our neighbor to the north(west) has a favorable exchange rate of .80 cents to the U.S. dollar. So luxury hotels like the Fairmont Pacific Rim in the naturally stunning city of Vancouver are super affordable. The city is one of the most ethnically and linguistically diverse cities in Canada: 52% of its residents have a first language other than English. “Van” is literally set within a rainforest, so nature enthusiasts will love walking along the waterfronts with views of the nearby mountaintops. For the culturally curious, I suggest weaving your way through the cobbled streets and shops in the historic Gastown neighborhood. Don't miss Kimprints, a shop supporting underprivileged street artists, or the Ok Boot Corral, a local bootmaker who has been in business since 1833. For an unexpected insider experience, get your sea legs on to go fishing for what’s in-season with sustainable seafood supplier, Organic Ocean. Afterward, you can bring your fresh catch to the kitchen of the Fairmont Pacific Rim to make fresh sushi. And let’s be real: What’s sushi without homemade sake? Check out Masa Shiroki, an artisan sake maker on Granville Island, for his locally made bubbly sake. Watch Oh the People You Meet's video for more insider tips on Vancouver.

*Savings based on all holiday package bookings with Flight + Hotel on CheapTickets.com from July 2017 to December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.
Chosen By: Amie O’Shaughnessy, founder and CEO of Ciao Bambino. After having her son, Amie searched extensively for credible resources to provide family-focused advice, direction and useful accommodation information. She quickly realized that there were no relevant resources available, particularly for a discerning traveler, so she decided to help solve this problem and started Ciao Bambino.
In 2014, CheapAir.com also analyzed nearly 2 million international trips covering 3,184 markets. International flights usually open for booking slightly less than a year in advance. CheapAir.com found that prices “stay fairly flat for a few months” after flights open for booking – but, of course, not all of us are ready to lock down travel plans nine months in advance. After the initial flat period, prices “start to creep up slowly, until about 90 days before departure when the pace of increase starts to accelerate.”
^Prices shown are per person based on double occupancy and include all airport, flight, and hotel taxes and fees except resort fees which are charged by the hotel upon arrival. Prices are valid for flight + hotel packages for the length of stay listed above to the featured destinations on the departure dates listed above. Pricing may differ when traveling from different origins, for longer than the length of stay shown, to different hotels not listed, or on dates not listed above.
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.

* This is the largest savings for simultaneous booking of flight and hotel from July 1, 2015 to June 30, 2016, and not the discount rate or amount for your booking. Savings calculated based on the cost of a Flight + Hotel booking on Travelocity.com as compared to the aggregated price of the full published fare given by the airline and the cost of your hotel for the same travel products for the same travel dates when made separately. Savings will vary based on the origin/destination, length of trip, stay dates and selected travel supplier(s). Savings are not available on all packages. Please confirm the actual discount rate/ price on the booking page.

Why: Colombia isn’t usually thought of as a value destination, but due to the strong U.S. dollar, it has become one of the most compelling destinations in the world for those willing to venture off the beaten track. Travelers in the know are loving Barichara, one of the most beautiful small colonial villages in the Andes. Stay at Casa Barichara for under $200 a night and dine at El Carambolo, a quaint B&B rich with personality and the perfect fit for those searching for authentic, Colombian hospitality. Though not a typical tourist destination, Barichara is perfect for adventure travelers who enjoy activities like paragliding. A trip to Barichara can be paired with the town of Salamina, where travelers will find quirky architecture and a renowned coffee production, and/or the vibrant city of Medellin, which boasts music, museums, nightlife and friendly people.
Of course, “top-notch guest services” is subjective. You could stay at a five-star hotel where the concierge is snooty and there’s constant construction, whereas you could find a gem of a two-star hotel where you’re treated like royalty by a warm, welcoming staff. That’s why it’s so important to value guest reviews over star ratings. Guest reviews give you an indication of what it’s actually like to stay at the hotel.
The first thing you need to know is that an all inclusive package was first created by the French corporation Club Med in the 1950s. The first location was opened on the Island of Mallorca, and thanks to Baron Edmond de Rothschild it soon expanded. Each location chose a series of services to be offered as a package for a price. However, the very first location also operated on this model.
Why: Peru’s northern beaches are an excellent option for budget travel, and Trujillo is no exception. The vibrant coastal city is awash with warm-colored colonial façades dating back to its status as a colonial powerhouse, and it offers excellent cultural and adventure activities, as well as upscale restaurants that are surprisingly affordable ($10-15). Accommodations are also very inexpensive; for example, the four-star Costal del Sol Wyndham can run as low as $65. Trujillo is home to the former capital of the Chimú people, the behemoth archaeological site of Chan Chan. Its Spanish-influenced architecture and bohemianism were an inspiration for the illustrious author Cesar Vallejo, and it continues to keep traditions alive by hosting prestigious events such as the month-long Marinera Dance Festival. For some action under the sun, check out the famous beach Huanchaco, Latin America’s first designated world-surfing reserve. Watch wave chasers in their caballito de totora boats and cool off with a plate of fine ceviche at its birthplace. Trujillo flies under the radar for tourists who focus on Cusco and Machu Picchu, but with its rich heritage — in addition to year-round sunshine, delicious food, vibrant dance and beaches — you’ll have plenty to write home about.
Chosen By: Michaela Guzy, an American media executive, entrepreneur and on-air show host. She is the executive producer for two online television shows, Michaela’s Map and OhThePeopleYouMeet. Based in New York City, she is also an adjunct professor at New York University School of Professional Studies, where she teaches a course called "Travel Storytelling: Creating Video Content."
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.
Travel Auctions. There are two kinds of travel auction sites. One allows you to enter your preferred travel dates, destination, and class of service (such as economy or business class), and travel companies compete to offer the lowest-priced trip that meets your criteria. Flightfox is one site that operates this way: It charges a per-trip fee, and while the exact price depends on the trip itself, you can expect to shell out around $30. The other type of travel auction operates the opposite way: Companies offer flights, hotels, or packages, and users can bid on the trips. When the auction closes, the top bid wins. SkyAuction.com operates using this model. It’s free to bid – though you should be aware that additional taxes and fees are unlikely to be included in your bid price, so you will end up paying more than your bid if you win.

* Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.
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.

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.
By placing an item in your cart, the company can tell that you’re in the market. This makes you an incredibly valuable potential customer, and it doesn’t want to miss out on your business. If you entered an email address, watch your email over the next couple of days to see if the company has taken the bait. And don’t forget to either follow through with the purchase or clear your cart after a few days so you don’t make an accidental purchase down the road.

Why: The second largest city in Morocco, Fez has an enchanting souk, lively markets, fascinating leather tanneries (which you can sniff out before you see) and quaint cafes serving Moroccan mint tea and local pastries. Fez is also filled to the brim with palatial riads, Moroccan homes built around a central courtyard or garden, which feature cozy rooms and rooftop terraces where you can relax after a walk through the bustling labyrinth of alleyways right outside your front door. Prices for a double room in a riad can be as low as 550 dirhams ($60), while a tangine dinner is around 50 dirhams ($6). Step inside a medersa, a theological college, to marvel at the splendid architecture and tilework and get a scrub at a hammam for a fraction of the cost of a spa in the U.S.

Weekend getaways – leaving Friday and returning Sunday – are awfully convenient if you work a Monday through Friday job, but you can expect to pay handsomely. According to Expedia, which releases an annual Travel Trends White Paper, you’re likely to pay 20% less for a flight that departs on Thursday and returns on Monday than one that departs on Friday and returns Sunday.

Are you on the hunt for cheap vacations? Perhaps you're looking for a luxury honeymoon at an all-inclusive resort. Maybe you’re scouting for a last-minute family vacation package with a hotel that’s suitable for children of any age. No matter what kind of vacation you want to book, we’ve got the best deals to help you save money on your upcoming travel.
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