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!
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.
Seats are limited and may not be available on some flights that operate during peak travel times and holiday periods. Flight and hotel rates may vary by day of week. Surcharges may apply to weekends, holidays, and convention periods. Flights available on published, scheduled service only. Rates may be subject to change until purchased. All Rapid Rewards® rules and regulations apply. Discounts are valid per reservation before taxes are applied. Offer not valid on existing reservations and may not be combined with any other offer. Subject to availability. Restrictions apply. The Mark Travel Corporation is the tour operator for Southwest Vacations.
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 Offer not combinable with all specials and may be changed or withdrawn at any time.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.
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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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.
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.

Hotel Tonight. While Hotel Tonight is an app that bypasses direct communication with travel companies, it can still be a great source for good, last-minute deals. Hotel Tonight takes advantage of hotel owners’ desire to fill empty rooms by enabling last-minute bookings at up to 70% off standard rates. It’s available for iPhones, iPads, and Android devices.


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.”
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.
^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.
Why: The Central Coast runs roughly from Santa Barbara to Monterey and the string of small towns between San Simeon and Pismo Beach is an unexpected surprise for many California coast road trippers. This is where SoCal surf town meets fishing village, and otters and elephant seals share the spotlight with European masterpieces at the Hearst Castle. Veer away from the coast and in a few minutes you'll find yourself at the wineries of Paso Robles, with tastings that are half the price of Napa and Sonoma. Adelaida is open daily; for a special hilltop tasting, try their Vineyard Tour, Taste and Tailgate. An emphasis on eating local and fresh creates foodie-worthy dining options throughout the region. Pismo Beach and quaint Moonstone Beach in Cambria offer the largest selection of lodging with the best value outside of the holidays and summer. Guests at Cambria Shores Inn relax each evening in Adirondack chairs positioned perfectly to take in the sunset. Afterwards, take a five-minute stroll to Sea Chest Restaurant for local seafood or drive to the Cracked Crab in Pismo Beach where the Deadliest Catch crew dined and all things crab are on the menu.
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.
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.
Many people take their Puerto Vallarta vacations at any time except the summer for a couple of reasons. For starters, the weather is usually nice in other places during the summer, so there is no reason to visit a tropical location. Secondly, Puerto Vallarta gets a lot of rain in July, August and September, which can quickly ruin a vacation. These months are cheaper, however, so you can find a great deal. Do not miss the Festival Cultural de Mayo held during the last week of May and first week of June. This festival celebrates the city’s birthday, and festivities include displays of local talent in art, music, food vending, and traditional bullfights.
Why: Oaxaca de Juarez is one of the most beautiful destinations to travel to in Mexico. Colorful markets, charming architecture, cobblestone streets, fun festivals and delicious food are just part of the attraction. Stroll through Oaxaca’s main square, the Zócalo, and relax at a café, people watch and be entertained by dancers and singers in the evenings. Just a few minutes walk from the square is the Mercado Benito Juárez, where you’ll find embroidered goods and straw baskets. Continue walking the pedestrian street called Calle Macedonio, where you’ll find art galleries, cafes, shops and boutique hotels. Visit the Santo Domingo de Guzmán church and monastery that dates back to 1555. Don’t Miss the Museum of Oaxacan Cultures, where you can see the treasures found on Mont Alban — the skull covered in turquoise, carved jaguar bones, gold jewelry and ornaments for a nominal fee. Hungry? Stop by at the food market 20 de Noviembre, where you’ll find piles of fried grasshoppers (chapulines) and Oaxaca cheeses, tamales, meat-filled tortillas, tlayudas, chocolates, coffees and seven types of mole. Get a taste of local dishes at food stalls for under $5 or free Mezcal tastings at Mezcaloteca. It’s easy to find your way around this town, but if you prefer to join a guided walking tour, contact Enjoy Oaxaca — they offer several tours from city tours to day trips to see Mont Alban, Mitla Ruins, Hierve el Agua bubbling springs and the petrified waterfall, as well as cooking classes and many festival tours including the Day of the Dead. Where to Stay? There are several boutique hotels and quaint B&B’s in town. You can reserve a room at Parador San Miguel Oaxaca for as low as $86 per night.
Hawaii - 60th Anniversary Hawaii Vacation Sale: Valid on new bookings made 10/29/18 - 1/13/19 for travel 10/29/18 - 12/31/19. Accommodation at participating resort and roundtrip transpacific airfare required. Room rate savings and minimum night stay vary by participating resort. Travelers will receive a voucher valid to buy one activity and get one activity of equal or lesser value for 60% off the retail value redeemable at any Pleasant Activities Center or the Pleasant Holidays Island Orientation in Hawaii or via the Hawaii Call Center by calling 1-888-229-7770. Fees and surcharges are excluded and must be paid for both tours. Limit of one discounted activity per booking. Offer does not apply to activities involving flights (plane or helicopter). Complimentary roundtrip shared airport transfers valid to/from HNL and any Waikiki hotel or resort in Pleasant Holidays' Oahu portfolio; offer does not apply to any hotels or resorts outside of Waikiki. Activity voucher and airport transfers have no cash value, are non-transferrable, are not combinable with any other offers, apply only to the vacation on which they were booked and expire at the end of booking's travel dates. Offer subject to availability and may be changed or cancelled at any time. Certain restrictions and blackout dates may apply.
Why:  For an epic adventure that won't break your travel piggy bank, head to the Komodo Islands , named one of the New 7 Wonders of Nature. Most of the islands in Indonesia are incredibly undermined because of how popular Bali is, but Komodo and its surrounding islands are definitely worth a visit. As the name implies, Komodo is the native home of the terrifying mini-Godzillas known as Komodo Dragons. To see them, you go on an incredible boat tour that takes you to a tri-color beach island and swimming with wild manta rays. Getting to Komodo from Bali costs about $40 by boat or $200 for a flight, and accommodation and food is super cheap because, well, it's Indonesia after all.
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
* All airline related taxes and fuel surcharges are included. Prices are per person, based on double occupancy, and are subject to change prior to purchase. Some foreign authorities require fees at arrival or departure that must be collected directly from the passengers at the airport. Airline-imposed baggage fees may apply and be due at the airport; please consult your airline prior to departure for the latest fees.
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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