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.
I’ve spent a few weeks on Boracay, but not in early November. From what I’ve read, the monsoons there are usually not too bad, and it’s mainly a matter of a couple of hours rain in the afternoon on the bad days. Throughout the Tropics it’s very rare to get rain all day on any given day, and I’ve spent many months in those areas during rainy seasons. So early November isn’t ideal, but if it’s the only time you can go I still think you’ll enjoy it. One nice thing about Boracay is that the hotels are all basically on the beach or right off the beach, so even if it does start raining you can be back in your room in like 2 or 3 minutes. Best of luck with this. -Roger
Vietnam might be your best choice of the three. Most people (if they can) fly into Hanoi and fly out of Ho Chi Minh City (Saigon) or the other way around. Again, you can travel between them by train, although getting tickets can be a bit complicated. Hanoi is really interesting and nice (and super cheap). The best tourist city in Vietnam is Hoi An, which is between the two big cities. There’s a nice beach there and a bit farther away is Denang, which has large resorts along an excellent beach. Nha Trang is another good beach city in Vietnam, but probably not great for families. Ho Chi Minh City is bigger and more crowded than Saigon, but it’s also more modern (and hotter). You could spend two really nice weeks going north to south in Vietnam with a long stop in Hoi An.
At the Kimpton Rowan Hotel, admire the appealing outdoor art while you have a quick bite at Juniper Table or head to the roof for dinner at the 4 Saints with its menu of seasonal Mediterranean-style dishes. From the restaurant and rooftop High Bar, you’ll feel as if you can reach out and touch the San Jacinto Mountains. The Palm Springs Art Museum, Indian Canyons, golf, casinos, luxurious spas, and the Palm Springs Aerial Tramway to the mountain top are just a few of the many things to do. Visitors can fly into Palm Springs International Airport or drive about three hours from Los Angeles.
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
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.
Southeast Asia is easier to deal with, and there are cheap flights connecting in the Middle East and landing in Bangkok, Kuala Lumpur, and Singapore. Each of those is a very interesting city, and there are many smaller places to go in the same region. In Malaysia there is Penang and Melaka. In Thailand there is Chiang Mai and quite a few others in that area. In Laos you can visit Luang Prabang, which sounds like it could be a winner for you. And there is also Siem Reap, which is home to the amazing Angkor Wat temple complex.