If you are looking for an all-inclusive resort with reasonable airfares from Chicagoland, your best bets will be in Punta Cana, Dominican Republic, or the Cancun/Playa del Carmen area. Both have everything on your list, except perhaps wild life, depending on how you define that. You can get cheaper flights into Cancun, and there is a wide variety of offerings once you are there. If you don’t think you want to leave the hotel much, then stay in the Cancun hotel district or along the Maya Riviera nearby. But if you want to interact with a real and lovely town, then stay in Playa del Carmen or over on Cozumel. There are many nearby activities and some very interesting ruins.

Most hotels these days include at least a small refrigerator, and some even include a full kitchen and stove. This is great because it allows you to shop locally for some fresh food options. Search online for nearby farmer’s markets or grocery stores and see if you can pick up some local meats or fresh veggies to have in your room. This is more likely to be an option in the warmer months.

We spent a month in Costa Rica last year and although we thoroughly enjoyed the trip, we don’t tend to be “repeat customers”, so we’d like to venture somewhere new (we saw that you had mentioned this as kid-friendly a few times, so just wanted to let you know that we’ve already been there). Some available attractions and activities would be ideal, but, we’d also quite enjoy the beach towns of some sort. We love hostel type of accommodations, aren’t overly-indulgent and can get by on a fairly modest budget. We are of the mind-set that spending more time, is more valuable than spending more money.
New Zealand will also be crowded, but the country is otherwise mostly empty so it is still wonderful. You could fly to Auckland for one day or so and rent a campervan/motorhome. Drive it for 3 or so days on the North Island, and then onto the ferry to the South Island for the rest of your time. The South Island is far more scenic and less crowded. You’ll be doing some driving and looking, but after a few hours of that you can stop at a campground and have plenty of things to do such as hiking or water sports and much more.

You mention New Zealand and of course it’s summer there then, so it would be a good choice. However, all of these places will be crowded and near peak hotel rates if they are warm. So I’ll be happy to give you advice if you tell me if you’d rather visit one or more European cities in the cold season, or if you are looking for a warm place like New Zealand where it will be fairly crowded. By the way, the southern European cities such as Rome and Barcelona are lively and enjoyable that time of year, as the Christmas season goes on, and there aren’t too many tourists except for a few that travel to see their families around the holidays. So it can be a good time for southern Europe, as long as you don’t mind wearing a jacket or jumper during the day, and maybe a bit more in the evening. Give me a bit more guidance and I’ll be happy to try to help. -Roger
There are many other Thai islands that could also be ideal and have what you are looking for. Another option is Boracay Island and I mention it because I spent an evening hanging out with some guys visiting from Saudi Arabia and they liked it a lot. The weather won’t be “cool” but it should be nice, and they do have very good nightlife in the Boat Station 1 area.
Cambodia could work because Siem Reap is inland and the amazing Angkor Wat temples are worth a full day or two, and the town of Siem Reap itself is quite nice. You could actually combine a couple days in Siem Reap with a few days in Bangkok, and take a (cheap) luxury bus between the two. Bangkok is a really fascinating city with a lot to see, plus it’s a great transport hub. The other main non-beach option in Thailand is the city of Chiang Mai, which is wonderfully inexpensive with quite a bit to see. It’s even a bit cool during December, so that might be a nice change of pace from India. Many people are also going to Myanmar these days, although I haven’t been yet so it’s hard for me to recommend it. I’d say if you combined 2 or even 3 of these places you could have a very interesting holiday.
The rainy season usually ends early in November in Siem Reap, and the tail end of it is rarely fierce, so this is an ideal month to hang out in town and spend multiple days at Angkor Wat. November is actually the coolest month of the year, by just a bit, at least during the days, so most people will appreciate more moderate temperatures when climbing up and over all the temples.
It would be hard to beat Chiang Mai for its combination of great November weather and low prices. Even though it's officially the start of the high season for hotels, the beginning of the month is usually very slow anyway, so bargains are common. Hotels in Chiang Mai are among the best bargains in the entire world, so even if you do have to pay full price for a room it'll be cheaper than a dorm bed in most European cities.

Lace up your boots for an end-of-year adventure at the wild ends of the Earth. December is the ideal time to explore Patagonia’s mind-blowingly beautiful Torres del Paine National Park. Embark on an epic trek along the eight-day circuit, or take the four-day ‘W’ trek for Instagram-worthy views of Los Cuernos (the ‘horns’), the region’s iconic jagged granite peaks. Similarly breathtaking experiences can be had diving the coral reefs around Thailand’s Similan Islands. Beneath the sparkling surface of the ocean you’ll find sharks, barracuda, rays and green and hawksbill turtles – it’s Finding Nemo brought to life.
If you’re pretty simplistic when it comes to food, you can always bring nuts with you. They last long, they taste great, and they’re packed full of fats (if you choose correctly). Macadamia nuts and Brazil nuts are among the top high-fat nuts out there, and they’re well worth the extra cost if they save you from an accidental cheat right at the end of a great vacation.
If those flights are too expensive you might think about going somewhere else in Mexico or to Costa Rica. The area around Cancun including Playa del Carmen and Tulum and Cozumel has a LOT going on. And if you’ve been there you could instead go to the Puerto Vallarta area, which is very different and also great. For activities though it’s hard to beat Costa Rica. I think they invented zip-lining and the country is about one-third national parks with all kinds of fun activities. Let me know if you have any other questions. -Roger
Hmmm…there may not be a Wow Factor in Puerto Rico, especially if you are that used to Caymen. I was thinking more about a really nice place that was easy and with great weather. Costa Rica could have the Wow Factor, however. The country is something like one-third national parks and it is packed with great scenery and adventure activities. It is the zip-lining and canopy tours capital of the Americas, so there are many great options along those lines. And there is the volcano and hot springs and really nice beaches. I’m not sure what you’d consider a Wow Factor, but Costa Rica is probably the most Wow destination other than Hawaii.

The traffic in Bali makes sightseeing notoriously challenging in June through August, but November is less crowded so it's a good time to come and spend a day in Ubud or even take a tour of the towns along the northern shore. In fact, if you want to avoid the huge Kuta crowds altogether you should consider basing yourself in the Lovina area of the north shore. It's as lovely and charming as the whole island was 20 years ago, but that may not last.

The fastest high-speed trains between those cities only take 2.5 hours, although most departures are closer to 3 hours. Definitely take the train and also buy the ticket as far in advance as possible for the lowest fare. Not only is it FAR quicker than flying (and of course the coach), but it’s far more comfortable and more enjoyable. This is a link to the official Spanish rail site. The scenery isn’t all that special, but it’s still interesting. Have a fantastic trip. -Roger
Pay homage to the Native American heritage of the U S of A by taking in the sights and sounds of Arizona’s capital city for pure rest and relaxation before the holiday season. Phoenix anchors a sprawling, multicity metropolitan area known as the Valley of the Sun, which is highly regarded for its luxury resorts, vibrant nightclubs, designer golf courses, and long lasting sunshine and warmth—even through the winter months. Attractions include the Heard Museum and the Pueblo Grande Museum & Archaeological Park. Be sure to check them out!
Far from the crowds and heat of summer, a visitor to Rome in December will find that it’s a lovely time there, with fewer lines at popular tourist spots, more attractive prices, and a chill in the air. With a warm jacket, comfortable shoes, cozy hat and gloves, you’re ready to explore the Eternal City. Stroll through the main streets to enjoy colorful lights, decorated trees, and Nativity scenes. The Piazza Navona hosts a Christmas market, and stores welcome shoppers with longer hours and attractive displays. Rome’s Jewish community celebrates Hanukkah with a large Menorah in Piazza Barberini where candles are lit each evening of the eight-night holiday, this year from December 2–10. The Catholic community celebrates the Immaculate Conception on December 8 when the Pope leads a procession from the Vatican to the Piazza di Spagna. December is the perfect time to visit the Vatican Museum, Sistine Chapel, St. Peter’s Basilica, Colosseum, Trevi Fountain, and museums that are usually filled with tourists during warmer months. Even without crowds, it’s still most convenient to book ahead through a tour company such as City Wonders or Access Italy, for no-wait entry, professional guides, and early admission. Food is always one of the great pleasures of a visit to Italy, and in December, a warming plate of spaghetti carbonara or hot chocolate and seasonal panettone taste especially good. The new Pantheon Iconic Rome Hotel, Autograph Collection is a convenient home base in the center of the action with a beautiful rooftop overlooking the Pantheon. 
Santa Barbara has earned its nickname, “The American Riviera,” with its stunning coastline, lush landscapes, cafes, restaurants, and year-round Mediterranean-like weather. Sandy beaches invite sunbathers, and for those interested in more activity, there’s biking, paddle boarding, surfing, and kayaking. In the heart of Santa Barbara County wine country, the city presents more than two dozen downtown tasting rooms on its “Urban Wine Trail.” The artsy “Funk Zone,” with a variety of cleverly designed eateries and shops, is just blocks from the beach. The community is recovering from devastating fires and mudslides, and its resilience is apparent with new hotels, restaurants, and attractions. The Montecito neighborhood, particularly hard hit by the tragic events, is home to the recently renovated Montecito Inn and its new dining venues, Phillip Frankland Lee's The Monarch, and the suave Chaplin’s Martini Bar, commemorating Charlie Chaplin, one of the hotel’s original owners when it was built in 1928. The elegant oceanfront Four Seasons Resort The Biltmore Santa Barbara offers a luxurious spa and views of Butterfly Beach. Less than two hours north of Los Angeles, Santa Barbara celebrates the holiday season with colorful lights, a Holiday Parade (Dec. 7), Harbor Boat Parade with fireworks (Dec. 16), European-style Christmas market, and the traditional "Nutcracker Suite" at the Granada Theater.
Thanks for the kind words and I’m happy to hear that this info helps. The Mount Rinjani ash cloud situation is also a mystery to me at this point. My plan was to fly into Bali more or less for the full month of February, but according to the news it does seem possible that the skies in the area will still be unsafe at that point. I will already be in Asia and if the Bali airport is still closed I’ll just go to the Philippines or Malaysia. But I wouldn’t book a long-haul flight into Bali for the coming months at this point, at least not unless I knew I could change it cheaply if the flights are canceled.
In spite of its image of being blazing hot all the time, December in Cairo can actually be on the cool side, at least in the evenings. This is great though because almost all the important sights are outdoors and requite a lot of walking between them. For 9 months of the year it can get very hot doing that, so these few cooler months are ideal for visiting the famous sights.
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