Anonymous wrote:Great ideas! Thanks!

I think they really liked Chicago because they just had lots of quirky and unique things to do. They loved The Second City, mob tour, architectural tour, comparing pizza. They also liked seeing some iconic things like Wrigley Field and taking the L.

Based on that, my suggestion is Boston.

You all enjoyed Chicago? It's in the midwest, you know. Ugh.

Anonymous wrote:Toronto

I have been in Chicago and Toronto. Chicago was amazing. We had so much fun. So much to do. Compare to that to Toronto was just plain boring. They are not in the same league.

Of course if someone loves Chicago... go to New York.... or Amsterdam

There aren't a lot of cities as great as Chicago. The one downside, and it's a big one, is the brutal winter weather. I couldn't live with that.

Anonymous wrote:

Anonymous wrote:I came to suggest Portland, OR but OP's mention of "quirky" things to do makes me want to suggest St. Louis, MO, specifically the City Museum. Hard to describe but so cool and fun.
https://citymuseum.org

I second this! Was in St. louis for a conference earlier this year and the city museum is very cool.

Not St. Louis imo, horrible city. The one museum might be cool but the city overall is terrible. Go to New York, Boston or Nashville.

Detroit
Traverse City
Minneapolis
Toronto
Montreal
Pittsburgh

Anonymous wrote:I came to suggest Portland, OR but OP's mention of "quirky" things to do makes me want to suggest St. Louis, MO, specifically the City Museum. Hard to describe but so cool and fun.
https://citymuseum.org

I second this! Was in St. louis for a conference earlier this year and the city museum is very cool.

Chicago is GOATed

Anonymous wrote:Great ideas! Thanks!

I think they really liked Chicago because they just had lots of quirky and unique things to do. They loved The Second City, mob tour, architectural tour, comparing pizza. They also liked seeing some iconic things like Wrigley Field and taking the L.

I used to live in Chicago. If above are why they like Chicago then I would say definitely New York.

New York had got all of the above times 10.

Parts of Berlin remind me of Chicago.

My college and YA kids and niblings also love Chicago. Other cities they’ve enjoyed are London, LA and San Francisco.

I came to suggest Portland, OR but OP's mention of "quirky" things to do makes me want to suggest St. Louis, MO, specifically the City Museum. Hard to describe but so cool and fun.
https://citymuseum.org

Detroit.

The Motown Museum, the Henry Ford museum, Greenfield Village, the DIA, Detroit pizza at Buddy's, the Detroit Historical Museum, the Tigers, Lions and Red Wings and Pistons, the coney islands.

I live here now and it's a fun city.

Anonymous wrote:Great ideas! Thanks!

I think they really liked Chicago because they just had lots of quirky and unique things to do. They loved The Second City, mob tour, architectural tour, comparing pizza. They also liked seeing some iconic things like Wrigley Field and taking the L.

Second City and architectural walking tour/boat tour are Chicago highlights.

For New York, I recommend Broadway and there is a one or two-man Hamilton the Musical walking tour of Manhattan that is great. I also have my eye on a tourist bus that drives you around while stopping to view scheduled street corner performances. The Tenement Museum is frequently recommended for young history buffs.

https://experiencetheride.com/?gad_source=1&gad_campaignid=22106672333&gbraid=0AAAAAp1YvG3o4qONGF2mdTZOQ8pzX7_eF&gclid=CjwKCAjw1dLDBhBoEiwAQNRiQcYzHjHzWzBb2W684exmfoPqj6WXjukXeA7fr09Lum16kijMLehYshoCOgkQAvD_BwE

I like Chicago and also like NYC and London so much. Boston has its charms but is maybe too oriented around old-timey Freedom Trail type tourism for the first timer. But, that could easily be overcome by going beyond the obvious.

I am a Pittsburgher. It is a beautiful setting and you can put together a fun weekend. But it is smaller than these other Tier 1 cities. So you'd have to pay attention to scheduling to have a great short visit with teens. The Andy Warhol Museum is probably a good choice based on your comments above. If you haven't been in a submarine, the Science Center has one. The Aviary is interesting for bird lovers. I like the Pitt Nationality Rooms. It is hard to line up visits to Pittsburgh with great theater. It exists but never when I'm home visiting relatives. There are also some industrial history tours that I have my eye on but have not been able to schedule because I mostly pass through at big family holidays like T-day, Easter, etc.

New Orleans