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.

Enjoy an all-inclusive vacation from the HotelInn Hotel in sunny Jamaica for 5 nights and book a 40% discounted getaway to Montego Bay, home of idyllic beaches, deep seas, good vibes, and lush jungles. What's Included? Based on two people sharing, this vacation deal includes round-trip flights, an all-inclusive 5-night stay at the 3.5-star Holiday…

*Unless otherwise noted, fares include ROUNDTRIP AIRFARE via U.S. certified air carrier, hotel transfers (in Mexico and the Caribbean), hotel tax, resort baggage handling, fuel surcharges and all pre-collected U.S. and foreign taxes and fees including September 11th Security Fee. Packages in Turks and Caicos or San Juan, Puerto Rico do not include airport transfers. Packages flying into Cancun but staying in Cozumel require supplemental ferry transfers at an additional cost. More details

Looking for something a little more luxurious? No problem. Check out our lists of the best hotels by island. If money is not so much the issue, we recommend Montage Kapalua Bay on Maui and Mauna Kea Resort on the Big Island. Both of these five star resorts are cozied up to beaches that have been voted #1 Beach in America by Dr. Beach. In addition, Montage Kapalua Bay is Hawaii’s newest Forbes Five Star property.  Another bonus? They both usually offer specials along the lines of “get the 4th night free.”
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.

U.S.: Alabama: Birmingham; Alaska: Anchorage; Arizona: Sedona; Tucson; California: Burbank; Long Beach; Ontario; Palm Springs; Sacramento; San Jose; Santa Barbara; Colorado: Colorado Springs; Connecticut: Hartford; Florida: Clearwater; Daytona Beach; Ft. Walton Beach; Naples; Marco Island; Key Largo; Melbourne Area; Cocoa Beach; Vero Beach; Miami; Pensacola; St. Petersburg; Tampa; Georgia: Atlanta; Savannah; Idaho: Boise; Illinois: Chicago; Indiana: Indianapolis; Kentucky: Louisville; Maine: Portland; Maryland: Baltimore; Michigan: Detroit; Flint; Grand Rapids; Traverse City; Minnesota: Minneapolis/St. Paul and Mall of Americaopens in a new window; Rochester; Mississippi: Gulfport and Biloxi; Jackson; Missouri: Kansas City; St. Louis; Montana: Billings; Bozeman; Kalispell; Missoula; Nebraska: Omaha; Nevada: Reno and Lake Tahoe; New Hampshire: Manchester; New Mexico: Albuquerque; New York: Albany; Buffalo; Rochester; White Plains; North Carolina: Charlotte; Greensboro; Raleigh; North Dakota: Fargo; Ohio: Cincinnati; Cleveland; Columbus; Dayton; Oklahoma: Oklahoma City; Tulsa; Oregon: Portland; Pennsylvania: Pittsburgh; Rhode Island: Providence; South Carolina: Charleston; Greenville; Hilton Head; Myrtle Beach; South Dakota: Rapid City and The Black Hills; Tennessee: Chattanooga; Knoxville; Memphis; Texas: Dallas/Ft. Worth; El Paso; Virginia: Newport News/Williamsburg; Norfolk; Richmond; Washington: Spokane; West Virginia: Charleston; Wisconsin: Green Bay; Madison; Milwaukee; Wyoming: Casper; Cody
Why: Okay, you may be thinking, “Isn’t Saint Martin/Sint Maarten destroyed?” Yes, this unique Caribbean island, which is half French (Saint Martin) and half Dutch (Sint Maarten), was devastated by Hurricane Irma. But now it’s on the mend. Saint Martin’s famed Princess Juliana International Airport has been open since late October 2017. The majority of the island’s electricity has been restored, and many beaches, bars, restaurants and businesses have reopened their doors. Because tourists are still wary, many hotels have discounted rates (like Hotel Mercure for $169 night) as well as gorgeous Airbnb properties starting at $50 a night. It’s a win-win. Not only will you save money, but your money will be spent on businesses and people who really need our help.

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: While the devastating hurricanes of 2017 impacted just a portion of the Caribbean region, it damaged some of its more cruise-popular spots, like Tortola in the British Virgin Islands, St. Martin, Puerto Rico, St. Bart's, and the U.S.V.I.’s St. Thomas, St. Croix and St. John. While all are under significant rehab and rebuilding — and most are actually now open to cruise ships and tourists, this could be a perfect year to explore more exotic islands. That’s because lines like Windstar, which had, pre-hurricanes, planned to offer BVI-centric trips, relocated ships to other parts of the Caribbean. The winning trip? We love Wind Surf, one of the line’s sailing vessels, with its trip out of Barbados; ports include Martinique, Guadeloupe, and Montserrat — all islands that heretofore have often been bypassed by established cruise lines. And get this: There’s plenty of cruise capacity in this region, particularly when it comes to small ship sailings. In part, excess cabins are available because many skittish travelers canceled their bookings. As well, they can typically be more expensive (look for $300 per person, per day) than big ship vessels. But do the math: Windstar, and other small ship lines like Crystal, Regent Seven Seas, Seabourn, Azamara, Oceania and Viking Oceans, can actually be quite a good value when compared to land-based properties because they’re more price inclusive. Look for deals that include cocktails, gratuities and shore excursions not to mention pre- and post-cruise hotel stays and, in some cases, airfare to the ships’ port of embarkation.
Just how cheap is it? The aftershock of the debt crisis can still be felt at plenty of Greece’s tavernas, restaurants, and supermarkets (though not so much in touristy areas). On a popular island such as Mykonos, you’re likely to spend at least €25 or more on a lush evening meal -- but you can also get a bottle of godly nectar and cook at your Airbnb or hotel kitchenette for a sliver of that. On smaller, less touristy islands and in some parts of Athens you’ll feel less of a wallet pinch, especially when it comes to accommodation.
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.  
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.
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.
JetBlue TrueBlue. U.S. News & World Report ranked JetBlue TrueBlue as number one on its list of Best Airline Rewards Programs. JetBlue primarily flies out of the East Coast and Florida, but if you live in either region and tend to travel domestically, this is one program to consider. Points can also be earned by traveling on its partner airlines, Emirates and Hawaiian Airlines. You can also earn points with hotel stays, car rentals, and “purchases with retail partners” – so you can rack up a whole bunch of points on a single trip.
The content on MoneyCrashers.com is for informational and educational purposes only and should not be construed as professional financial advice. Should you need such advice, consult a licensed financial or tax advisor. References to products, offers, and rates from third party sites often change. While we do our best to keep these updated, numbers stated on this site may differ from actual numbers. We may have financial relationships with some of the companies mentioned on this website. Among other things, we may receive free products, services, and/or monetary compensation in exchange for featured placement of sponsored products or services. We strive to write accurate and genuine reviews and articles, and all views and opinions expressed are solely those of the authors.
Why you should go: The landlocked country has a rich indigenous culture (por ejemplo: you can buy dried llama fetuses from colorfully dressed mamitas in the markets of La Paz), and a stunning range of landscapes, from rust-colored desert where dinosaurs once trekked to lush pampas and jungles to the otherworldly expanse of the Salar de Uyuni, where the horizon disappears between ground and sky. Adventurous spirits can find some of the cheapest paragliding in the world in Cochabamba, while mountaineers can tackle the 21,000ft high Nevado Sajama. The rest of us can wander around charming cities like Sucre, or take in the mesmerizing sunsets of Lake Titicaca, as beautiful to behold as it is fun to say. - Laura Yan, Thrillist contributor
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!
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