Malaysia is a favorite of mine, although it’s not really known for beaches. Again, it really depends on what you are looking for. Kuala Lumpur is my favorite city in Asia because it’s got such a great mix of things and it’s also pretty affordable, but not everyone is looking for a big modern city. I’m happy to help with more recommendations if you let me know more about your goals. -Roger
If you are going for one week I wouldn’t go all the way to Thailand, but if it’s two weeks I think it’s worth it. It takes most of a day in each direction, but flights are often reasonably priced, and everything there is cheap once you get there. I’ve actually lived in Thailand for 6 months and have visited many more times and it’s actually very easy and stress free once you are there. All the important signs are in English and nearly everyone you’ll encounter as a tourist will speak enough English to help you as well. You can get around by train or VIP bus for cheap, or fly to the islands for cheap. It’s very safe there as well. You could spend a few days in Bangkok and then head to one of the islands or take a train up to Chiang Mai.
I’m happy to help. As mentioned above, November is a very tricky time for a sunshine holiday because so many of the better places have their rainiest season then. I agree about the DR. It’s an excellent place for big all-inclusive beach hotels, but outside the hotels there isn’t much of interest unless you are fluent in Spanish and hopefully know a local. One you might consider is San Juan, Puerto Rico combined with some stops elsewhere on the island. November is part of the rainy season there as well, but I don’t think it rains all day very often. And the city of San Juan is excellent for nightlife and things to do, so even if you get a couple rainy days you should be able to find some things to do. By then it’ll be over a year since the hurricane and San Juan has already been close to normal for a while now. There is still some damage, but it would be easy to avoid.
Say Hydrated – This is a no-brainer and one of the most significant challenges for me. I never drink enough water, but it was hot this week in Florida when we were at Disney, and I could tell such a difference in how I felt when I was hydrated. I felt like it made it easier to stay strong and stick to eating low carb/keto as it helps to quench false hunger.
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.
Aside from Indonesia you might also consider Thailand, which has great infrastructure so it’s much easier to travel with young children. Phuket has by far the most options, and its rainy season usually ends in early November. For families I recommend Kata Beach and Karon Beach, which are both just south of the main shopping and nightlife town of Patong Beach.
And as you mention, Bali could actually work for you. I’ve spent two Decembers in Bali, and December is quite a bit rainier on average. Still I had a great time and it was sunny most of the days. The rain in the tropics (and Bali is almost ON the equator) tends to come down in 30-minute bursts rather than drizzling all day, so it’s usually pretty easy to avoid. The best part of Bali is there are loads of things to see and do, and the nightlife is excellent. The Kuta Beach area is fun for at least a few days, but I wouldn’t spend too much time there. You should also spend a few days in Ubud, which is very touristy but also interesting. And you could spend some time in Lovina, which is along the northern coast and it has all of the charm of Bali from 20 years ago before most of it got overbuilt. With all the temples and other local attractions, there is always something interesting to do, which is not true of many other places with great beaches and nightlife. Let me know if you have any other questions. -Roger
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.