Cities that are unexpectedly good
 

Heroica Veracruz, Veracruz state, Mexico. History, music, dance, food, coffee, culture, beaches, ruins, museums, aquarium. It's the hidden gem of Mexico beach cities.

One city that has pleasantly surprised me with its charm and vibrancy is Porto, Portugal. In addition, Porto is famous for its delicious port wine, which can be sampled at numerous cellars along the river. The city's rich history, delicious cuisine, and friendly locals make it a hidden gem worth exploring.

I was greatly surprised with Tallin, not the most popular tourist destination but the vibes of that city (specially in winter) will last in my memory forever.

Portland Oregon?!?!?! Really? I live in Seattle and am so surprised to see this post.

We were surprised and pleased with our stay in Amman, Jordan.

Grenada, Nicaragua. We'd planned to move around the country a bit but Granada had such a laid-back, non-touristed vibe with a lot of "lived-in" character. We just stayed there the whole time and made day trips to hike the Mombacho rim (saw sloths and monkeys, lots of orchids), boats out into the islets in the lake, etc.,

Belgrade is a vibrant city with a rich history, diverse culture, and a lively atmosphere.
I fell in love with the coffee, the people, and the pace of life. Traditional Serbian food is a very divisive topic! However, something that really makes Belgrade stand out in this regard is the friendliness of the locals.
If you have an income from the West, it is rather affordable. Here, I can afford a large apartment to myself with everything I could want in any neighborhood I choose.
Sure, there are downsides like anywhere, the indoor smoking, to get residency there is a mountain of paperwork... But I walk around without worrying about safety and even get smiles from random people on the street, and it’s a pretty great city in many ways.

I didn't know exactly what to expect but found Chicago to be the great American city that it was said to be.
They have a great waterfront that is paths and parkland for miles upon kilometres.
A wealthy city but it also has that sad neglected side to it like many U.S. cites do.
Overall, no regrets about visiting there and looking forward to visiting again.

Cape Town, South Africa: It offers an excellent blend of urban life and natural beauty. Highlights include Table Mountain, the V&A Waterfront, and the Cape Winelands.

I'm with you on that. Chicago can be less rowdy than other major cities in the US. And I am happy to say that it is expanding! But it cannot match the energy of NYC and LA! There are some safety concerns, too. Even the downtown area becomes desolate at night, and I always recommend tourists stick to the center and not wander too far away after sundown, like the Navy Pier.
NYC, in comparison, is less of a ghost town at night (but avoid going into Central Park after dark if you don't want to be robbed). I think Los Angeles is also a great option for tourists - there is lots of natural scenery and theme parks, but even then, I would never walk around downtown LA after 1 a.m.
By the way, did you visit Chinatown? I personally love that part of Chicago.