Chiang Mai, Thailand
in $690s-$790s RT
This might be the coolest town in Thailand.
Tourists tend to flock either to Bangkok or out to the island resorts, but Chiang Mai has been making a name for itself among those in the know.
It's just cool — laid-back, a little artsy, a little hippie, and never too in-your-face. It's become a haven for backpackers who want to see the "real Thailand," but despite its burgeoning popularity, it's still authentically Thai. It's a place to hang out and experience the local culture, while also stuffing your face on (insanely cheap) Khao Soi.
And it doesn't hurt that the surroundings are so jaw-dropping. From that ethereal white temple you've probably seen on Instagram, to those dreamy, quiet valleys soaked in greenery, you'll quickly realize why the good word-of-mouth is spreading :-)
Taking off ✈️
Tip Published: Sep 09, 2025
To:
- Chiang Mai (CNX)
From:
- Chicago (ORD) - $799
- Los Angeles (LAX) - $699
- San Francisco (SFO) - $783
- Seattle (SEA) - $791
How to Book
This is a Takeoff-only Flight for Jack's Flight Club Takeoff members only. For step by step instructions on how to book it you'll need to login or upgrade to Takeoff membership.