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: Alyssa Ramos, founder of My Life's a Movie and a solo female travel blogger, content creator, entrepreneur and social media influencer who travels the world full time and seeks to showcase unique destinations through her unique photography style and honest, detailed travel tips. Her motto is "Dreams Don't Work Unless You Do." Read about how Ramos went from broke to traveling full-time here.


Why: The Greek Island of Karpathos offers much of the same allure as chic Santorini and Mykonos, but with the advantage of lower prices. Karpathos is the second largest of the Dodecanese Island chain, which includes better-known Rhodes. Karpathos dates back to the 5th century BC, offering history buffs a way to have two trips in one, combining sun and sand with a step back in time. Ancient ruins can still be seen at Aghia Anastasia, while the island’s history can be studied in more detail in the Archaeological Museum. Beyond lounging on white-sand beaches, active travelers can choose from a selection of sports: fishing, windsurfing, snorkeling, scuba diving and sailing. Away from the well-worn tourist path, Karpathos has hillsides covered in vibrant wild flowers and small villages like Arkasas to explore. The island’s capital, Pighadia, is a modern city, but in small towns like Olympos, traditional dress is still worn day-to-day and life has the authentic feel of the past. Karpathos has many apartments and studios to rent, resulting in real savings. There are plenty of budget hotels under $100. Multiple restaurants and tavernas dot the countryside, where you can savor traditional Greek dishes at low prices.
Using a website like Hotels.com or TripAdvisor, set your minimum guest rating level high (start with four stars and above) and be open to hotels at any star rating. Once you’ve eliminated all but the highest-reviewed hotels, sort by price from low to high. As long as the hotels on the list have a reasonable number of reviews – around 100 or more – it’s a fair bet that the hotel makes the best of whatever amenities they have.
Priceline’s “Name Your Own Price” Option. When using Priceline, you can enter the day you’d like to fly (or the day you’d like to stay at a hotel) and the price you’d like to spend. Priceline comes back with an offer of a flight or hotel, if there’s something available that meets your criteria. You find out the times of the flight and the star rating and general location of the hotel, but you won’t get to know the airline or specific hotel name until you book. Priceline claims that you can save 40% off published prices by using this method. Priceline also offers traditional booking services if you’d rather know exactly what you’re getting.

Just how cheap is it? If you get yourself to Isla Grande -- part of the Islas del Rosario just off the country’s north coast -- it’s a tropical paradise for as cheap as you care to make it. Although there are fancier resorts available, at eco-hotels such as La Cocotera, Las Palmeras, or El Hamaquero, you can sleep in a beachside hammock for just $10 a night. For $20, you’ll also get you three meals, including a freshly caught and grilled fish dinner. Or, pro tip: A local can bring you freshly caught lobsters on request from anywhere between $10 to $30 a day. Sneak into the upmarket Hotel Majagua and grab a piña colada for $5, or go to the inland village for cut-price cervezas. (If you want more privacy, lodging starts at around $30 per room, and goes up to between $90 to $250.)


Why: The Greek Island of Karpathos offers much of the same allure as chic Santorini and Mykonos, but with the advantage of lower prices. Karpathos is the second largest of the Dodecanese Island chain, which includes better-known Rhodes. Karpathos dates back to the 5th century BC, offering history buffs a way to have two trips in one, combining sun and sand with a step back in time. Ancient ruins can still be seen at Aghia Anastasia, while the island’s history can be studied in more detail in the Archaeological Museum. Beyond lounging on white-sand beaches, active travelers can choose from a selection of sports: fishing, windsurfing, snorkeling, scuba diving and sailing. Away from the well-worn tourist path, Karpathos has hillsides covered in vibrant wild flowers and small villages like Arkasas to explore. The island’s capital, Pighadia, is a modern city, but in small towns like Olympos, traditional dress is still worn day-to-day and life has the authentic feel of the past. Karpathos has many apartments and studios to rent, resulting in real savings. There are plenty of budget hotels under $100. Multiple restaurants and tavernas dot the countryside, where you can savor traditional Greek dishes at low prices.
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: For an affordable and sun-soaked vacation, southern Portugal’s Algarve region should be hot on your radar. The city of Albufeira boasts a beautiful climate, fabulous beaches, inexpensive apartment-style hotels and a central location within the Algarve. There are over 100 different restaurants, bars and nightclubs, and Albufeira even has a charming Old Town with traditional Portuguese streets and plazas within the city center. The prices for both food and wine are extremely reasonable; be sure to sample the wines of Portugal. While summer remains the busiest and most popular time to visit, I love visiting in late spring — the weather is pleasant and sunny, there are fewer tourists and hotel rates are very affordable. Albufeira also offers easy access to nearby towns such as Loulé, with its famous market and an authentic slice of Portuguese culture. Rent a car to see the church of São Lourenço in Almancil, famous for its exquisite blue tile. Head north of Lagos to see Ponta da Piedade, with its towering red rock formations against the sea. Play a round of golf in one of the many beautiful courses in the Algarve. The place to stay: the Epic Sana Algarve overlooking Praia da Falésia, where you can bask in the sun at one of its five outdoor pools and indulge at the beautiful spa.
Some of the best cheap vacation packages include trips to Asia and Australia. Have you always wanted to explore the outback? Guided tours are the best way to experience the continent like a true outdoor adventurer. From India to Vietnam to China, excursions in Asia will leave you awestruck and satisfied. Who wouldn't feel like an explorer after visiting the Taj Mahal and trekking through bustling Hong Kong?
* 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.
We have three hotels that we highly recommend: Kaanapali Beach Hotel and Royal Lahaina Resort on Maui, and Royal Kona Resort on the Big Island. Both Royal Lahaina Resort and Royal Kona Resort offer “Best Price Guarantee” as well as a ton of options for creating your perfect vacation package. And Kaanapali Beach Hotel goes above and beyond to ensure that each package is providing the most value possible to visitors like you. Known as the “Most Hawaiian Hotel,” Kaanapali Beach Hotel keeps drawing its guests back with its authentic Hawaiian hospitality. You can also view our Maui vacation packages.
Why: When it comes to cheap destinations, you can not beat Thailand. Phuket is a beautiful beach spot that is famously known for nice people, affordable hotels and amazing food. Low season is in the spring and winter. (Don't go during summer because it will rain everyday.) Once in Phuket, head to Patong beach at night: The nightlife is something to see, with loud music and constant entertainment. The next day you should head to Phuket Town. With its colorful buildings, Phuket Town looks like you stepped into Portugal. Stay at Andakira Hotel Patong for under $50 a night. Before you leave Phuket, make sure you take a ferry for around $30 roundtrip to the Phi Phi islands: It's a two-hour boat ride, but so worth it.
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.
Then, sit back and wait. Some (but not all) websites are set up to automatically send a coupon or other offer to people who almost make a purchase but change their minds at the last minute. Coupon values vary dramatically, so you have to know what will be enough to sway you. You might only get a token discount, but it’s not unreasonable to see 10%, 15%, or even 25% off.
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.

Package vacations are a great choice for effortless traveling, as they are quick and easy to book and ensure that everything will be taken care of for you. For example, if your flight is canceled, it’s the travel provider’s job to find a new flight for you. You can rest easy knowing that your vacation will be stress-free and you are protected in case of changes to your itinerary.
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