2025 Compare Cities Rankings:
Kailua (Honolulu County), HI vs Chestertown, MD

#1 Most Comfortable Summer Cities

#1 Top 10 Cities to Beat the Heat

I have live in Kailua Oahu, HI for more than 27 years. I love this place but the cost to live here is becoming to much as I approach retirement. It also has become  More

Kailua is a perfect place to live if you like a relaxed and friendly neighborhood. It is close to local shops, local restaurants, beaches and ocean activities. Easy  More

We've been here for the past 10 years, and it is truly heaven on earth from an environmental perspective, but a Cost of Living comparison will scare the daylights out of  More

I have lived in Queen Anne's county most of my life, which is on the other side of the river from Chestertown. When I was younger, I remember ice cream shoppes, music  More

Chestertown is lovely. Because of the College, it has a real college town feel. It is very old however, so there are many people whose families grew up here. They make  More

Chestertown is lovely. Because of the College, it has a real college town feel. It is very old however, so there are many people whose families grew up here. They make  More