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!

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.
Most hotels with a website will have a short presentation of each room as well as of the features that are offered for free. It is possible for some vacation packages to have various restrictions. As a future guest you should always ask before hand what exactly is included in the price and what is not included. If there is a specific aspect you’re worried about, such as free internet access or tipping the staff, it is better to ask as to avoid embarrassing situations at the end of your stay.
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.
According to USA Today, the Better Business Bureau files well over 1,000 complaints in a single year from victims of “free” cruise scams. Other “too good to be true” deals may not be actual scams, but may require you to participate in a sales presentation, commonly for a time-share. Be alert, be skeptical, and be willing to put in the time to verify anything that doesn’t feel right.
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? 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.
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.”
Vacation rental prices vary as much as hotel prices. Case in point: A search of one-bedroom vacation rentals in Manhattan during September results in options ranging from $60 per night to $2,800 per night. Vacation rentals are ideal for longer stays (seven nights or more). Many vacation rentals require minimum stays, so if you’re hoping for a weekend getaway, you may have to look elsewhere.
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.
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.
Why you should go: With some 6,000 islands, Greece is the Mediterranean’s powerhouse beach destination. While only 200-some are inhabited, an island-trotting adventure for everyone here, whether you’re looking for wildlife adventures, historic discoveries, or quite frankly, drinking ouzo and boogying. Athens makes an energetic springboard into the Aegean, with its own archaeological ruins, hipster cafés, and hangouts ranging from dynamic industrial to retro chic.

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.


If you’re tempted to make a vacation-related purchase but are a little put off by the price tag, add the item to your electronic cart – but don’t go all the way through with the purchase. Before doing this, be very careful to make sure that it’s not a one-click purchase or a website where your payment details are stored, or anything else that will rope you into a purchase that you’re not ready to make.
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.
Why: Slovenia is in the heart of Europe and borders the alps and the Mediterranean Coast. It’s a country that has a little bit of everything — mountains, beaches, pristine lakes, 11,000 karst caves, castles, a Pannonian Salt Plain, healthy water springs and city life in Ljubljana, European’s Green Capital. No wonder it’s been called the New Zealand of Europe. One of my favorite towns to visit is Piran, located on Slovenian’s Istria on the Adriatic Sea. Explore this coastal town — a little Venice — and savor a fresh seafood meal for under $10. It’s the perfect place to visit on foot. Meander through the alleyways and visit the market. Climb up to the city walls and to the top of the bell tower for spectacular views. Or rent a bike and cycle through the countryside. It’s an easy day trip from Ljubljana, but if you plan to stay the night, check into a luxury four-star hotel like Hotel Piran for just $80 a night. How to get around? Visit GoOpti for airport transfers as low as $9. If you want to carpool from Slovenia to Italy or Croatia, check their site for great deals. For example, you can carpool from Ljubljana to Venice for as low as $18. Round About Slovenia offers deals for tours around the country and even Croatia (how about a $45 half-day tour to Lake Bled?).
For example, a writer for The New York Times searched for a long weekend getaway in Washington, D.C. and found a vacation package that looked like a tremendous deal. However, the hotel was 22 miles away from Washington. In other scenarios, the hotel might be fantastic, but your flight might have two stops and a 12-hour layover in Topeka. The bottom line is that it’s worth exploring package options, but be sure to scrutinize the individual components of the package to make sure you’re not compromising too much.
Why: The Golden City of Jaisalmer is often overlooked by travelers because of its distance from Delhi (a 14-hour train ride), but it is absolutely worth a visit for its stunning architecture and magical atmosphere. Situated in the heart of the Thar Desert, the Jaisalmer is made entirely of yellow sandstone and looks like an enormous sandcastle rising out of the desert. A visit to the Jaisalmer Fort costs 50 rupees ($0.80) and offers sweeping views of the city below; aesthetes will appreciate the intricately carved and painted havelis (homes). Don't miss stopping by the picturesque Gadisar Lake, dotted with beautiful temples, and taking a camel ride in the dessert.

Maui, nicknamed "The Valley Isle," is consistently rated by travel experts to be among the top island destinations in the world. Maui has some of the finest luxury beach resort accommodations and activities in the islands, especially along Kaanapali Beach. All of these high-end resorts amid the romantic beach backdrops make Maui a popular honeymooning spot. Read more about Maui


Most hotels with a website will have a short presentation of each room as well as of the features that are offered for free. It is possible for some vacation packages to have various restrictions. As a future guest you should always ask before hand what exactly is included in the price and what is not included. If there is a specific aspect you’re worried about, such as free internet access or tipping the staff, it is better to ask as to avoid embarrassing situations at the end of your stay.
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.
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.
Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on Cheaptickets.com of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.
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.
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.
From the blue waters and white sands of Mismaloya to the secluded shores and jade backdrop of Majahuitas, it would be easy to call Puerto Vallarta heaven on earth. But aside from its stunning beaches and natural landscapes, Puerto Vallarta has plenty more for budget travelers. Cruise the Rio Cuale Riverwalk, or tackle a challenging hike through the El Tuito jungle to reach the amazing Yelapa Waterfall.
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: La Paz is the perfect destination for those looking for a bit of adventure with the comfort of being in a vibrant, bustling city. Surrounded by the Bolivian Andes, La Paz is an outdoor adventurer’s paradise. Visiting during the winter season (May through October) is the best time for escaping to the slopes. If you’re looking for a real adventure, day tours to ski on one of the highest ski slopes in the world go for less than $70, including transportation and food. If you’re looking to stay more grounded, check out the local activities, such as Cholita Wresting, a La Paz specialty combining WWF and lucha libra. Or check out the Mercado de las Brujas (the Witches’ Market), an attraction not to be missed with locally handcrafted items and some herbal and folk remedies. The best part of all: You can live in near-luxury at five-star hotels around the city, with prices almost always less than $150 per night. Check out the Camino Real Aparthotel & Spa and the Casa Grande Hotel.
Bali, Indonesia is a bucket-list must: beautiful beaches, ornate temples, delicious food and stunning vistas—this island is where travel dreams become reality! Combine cheap flights with a super affordable 4-star hotel, and say hello to a honeymoon or vacation that won't destroy your budget. What's Included? Based on two people sharing, this vacation deal includes…
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