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.
If you’re a bit more on the timid side, you can always use Yelp and TripAdvisor to get good insights on places people have visited. As a disclaimer, some of the ratings may not be accurate on these sites, so make sure you go through and read some of the more recent reviews that people have written. We did this for a few of the places we visited and had no issues.
I like your comment about how “rainy seasons” are almost always overstated. I totally agree based on my own experiences and research, although there are a few places where they should be taken more seriously than others. On my most recent December trip to Bali (2.5 years ago, I think), I spent 30 days there and the rain only became a problem that one time I mentioned. It was just an insane cloudburst while taking a minibus from Kuta to Ubud, and in the end it’s actually probably my best Bali story. Aside from that, it’s very humid during Bali’s wet season, but even that really didn’t slow me down. The thing is, in Bali you are usually on or near the beach or a hotel pool (feeling the breeze) or in your air-conditioned room. Or you might be touring around to see temples and rice terraces and whatnot, and everything is outdoors and beautiful. When it does rain it’s usually over in 15 minutes, but often the rain comes over night. That kind of humidity can be a killer when visiting a city, but for me it’s a small issue on a tropical island like Bali.
I’ll be happy to try to help, but I’d really need to know your starting point because there are cheap places in different corners of the world, and it’s not worth flying halfway around the world to try to save US$20 per day. In mid December through January for beaches you should consider Thailand and perhaps also Vietnam. I’ll give you more information once I know where you are starting from. -Roger
Haveb been to kerela, Pondicherry, etc. we have coevred India a lot as we travel a lot and like exploring the world. We wanted to step out of India for this holiday. I was thinking of Maldives or Malaysia. 4-5 hour flight should be manageable but extending that more would be stretching it a bit i guess. So heer i am still confused and lost. Thaailand is an option again as there are several beaches which are serence and unexplored but i would not want to go to Phuket as its very crowded and touristy. Can you suggest a better island in Thailand which is quite, blue green water and less crowded.
The Maldives is amazing for relaxing beach holidays and it’s within your range. The tricky thing for most people is that it’s quite expensive for a shorter trip. Of course the Maldives is famous for its water villa resorts, and those water villas start at around US$350 per night. Nearly all of those resorts also have island villas and rooms and those can start at as low as US$100 per night, but you also have to pay for a speedboat or sea-plane transfer from Male Airport to your resort. That can be as low as US$100 per adult for the closer speedboat islands, and up to US$600 per adult for the more remote sea-plane islands. On a shorter stay, that obviously adds to the price. Speaking of that, I run another site all about overwater bungalows and I have links from an article on this site about the cheapest overwater villas in the world. Have a look at that list as it will show you the more affordable options in the Maldives, as well as even cheaper options in Malaysia and elsewhere.
Based on your description, you definitely want to go to Costa Rica. The neighboring countries have many similarities, but Costa Rica is the shining star in Central America for tourism. They have endless national parks and nature sights, but also lovely beaches and adventure activities. The area in the north around the town of Tamarindo is the more luxurious part of the country, but there are many other beach towns on both coasts that could work for you. You will also probably want to spend one or more days in the Arenal volcano area, which has many other great activities. The Caribbean coast is more laid back and less family oriented, so better to focus on the Pacific. Have a great trip. -Roger
Traveling during the last ten days of December means crowds and exorbitant prices throughout much of the world, but the first two-thirds of the month—before holiday airfares and hotel rates go into effect—can be a serene, value-laden, and just plain lovely time to vacation. Europe is all decked out for the holidays—with locals generally friendly and in high spirits; in the Southern Hemisphere, spring is in bloom; and in the Caribbean, Hawaii, and Mexico, hurricane season is over, the weather is gorgeous, and there are free upgrades galore.