(1) If you're willing to fly economy, round-trip tickets from New York can range from $650–$1000 (note that this figure won't include any flights you want to take within Southeast Asia); and
(2) Hotel, tour, and food expenses are all what we would consider very affordable in Southeast Asia. I know some travel bloggers receive sponsored stays at the best and fanciest hotels, even in Southeast Asia (I'll point you to a few of those, too, even if I haven't stayed at them), and other travel bloggers are really into backpacking and hostels, but you can think of me as Goldilocks with dark black hair and a floppy sunhat—I'm not particularly interested in roughing it but also don't want to blow my entire budget on a hotel—although I may reconsider if I'm at a resort, especially if all-inclusive or if you're paying for other amenities or a lovely private beach.
Winter in Thailand lasts from November to February—but don't worry, winter in Thailand is relatively comfortable—temperatures range from 30–35°C, or 86–95°F, and humidity drops as well. While we were there, it was definitely still humid, so I can only imagine what it's like during summer. Winter is also just after the rainy season, which typically lasts from July to October. We were in Thailand for about 6 days the second week of November and had just one burst of rain, which lasted about an hour while the sun was still shining and honestly was kind of welcome—it cooled things down.
I would be surprised if there are any direct flights from anywhere in the U.S. to Chiang Mai. You most likely have to do a layover somewhere else in Asia. We flew EVA Air (a Taiwanese airline, which I'll review and post a link to in the future) from JFK in New York City to Taipei and then EVA Air again from Taipei to Bangkok. We spent the night at Amari Don Muang Airport Hotel in Bangkok (review to come), which is conveniently located right across the street (literally, you take a skywalk) from the international airport, before boarding an early-morning flight to Chiang Mai, which is in the north of Thailand.
There are so many hotels in Chiang Mai. We stayed in two while we were there—one, a very nice but economical (by U.S. standards) hotel and the other, a very nice hotel that nonetheless didn't break the bank. Stand-alone review posts are in the works, but suffice it to say that we thoroughly enjoyed both and would recommend that you check them out as well.
I like to stay, if possible, in hotels that don't feel sterile and American, and luckily there are a ton of hotels in Chiang Mai that fit this bill. Below are just a few suggestions; note that booking will vary based on when you book, what kind of room you book, and through which service—I've tried to provide a representative range):
Expensive
137 Pillars House ($750–$900)
Dhara Dhevi Chiang Mai ($500–$850)
We didn't stay at Dhara Dhevi Chiang Mai, but we made the trip out there to explore their hotel grounds and have some afternoon tea:
These are the main hotel grounds.
Just me in a random doorway on the Dhara Dhevi hotel grounds.
Duck salad, spicy Thai sausage croissants, and green tea at the Dhara Dhevi.
Mid-range
Ping Nakara Boutique Hotel and Spa ($175–$225)
Siripanna Villa Resort and Spa ($110–$200)
Puripunn Baby Grand Boutique Hotel ($140–$220)
We stayed at the Puripunn (review to come), which was amazingly lovely, both day and night.
Puripunn courtyard in the daylight.
Puripunn pool in the moonlight.
Budget
Rustic River Boutique Hotel ($35–$45)
Thannatee Boutique Hotel ($40–$60)
We stayed at Thannattee (review to come), which was very good value for the price and had a distinctly Thai (and non-sterile or American) feel about it.
I like courtyards. Can you tell?
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