Question for someone who has been to Manhattan and downtown Chicago

Yes as noted already by now, Oak Street Beach. Off of Division. Crowded though.

NYC and Chicago are very different and both quite different than other cities as well.

You want the Manhattan experience the only place to get it is Manhattan. You already know what that is.

Chicago is the next closest in the United States to that urban concentration (LA is larger in population but not an urban experience at all) but it is a big jump. Bigger though than Seattle, SF, and Boston.

Chicago is prettier. The architecture more significant and not so packed that you cannot appreciate the skyline. Not anywhere near as crowded and much more manageable to know where you are (“the lake is always east”). Must-do items as a visitor: both a river architecture tour and a walking one; Cloud Gate (“The Bean”) and its environs; Maggie Daly Park; The Art Institute (especially if you are fan of Impressionism). Rent a bike (Divvy stations all over the place) and ride around; it is much more bike friendly than NYC and not just the lakefront path. I wouldn’t recommend Navy Pier other than to know what it is and maybe for the view from the big Ferris wheel. Experiencing a game at Wrigley is worth it even if the Cubs weren’t good. The Cell (where the Sox play) not so much.

If you are an architecture buff then take an el ride out to Oak Park and go on a Frank Lloyd Wright tour too.

Yeah the safety comments made are ignorant. It is a huge problem heavily concentrated in a few neighborhoods none of which are close to where you are.

+1 on that

The best advice I can give you for visiting either Manhattan or Chicago is . . .
Don’t.

Aw, SNAP! In your face, Manhattan and/or Chicago!

I love Chicago, but it’s damn hard to get around without a car. Like the rest of the U.S., I suppose. This is why I love NYC even more.

Shouldn’t you be busy candling eggs or mowing the alfalfa or something?

I live in Chicago, more than 15 miles from where I work, and I own a car. I use it maybe once a month.

If you’re visiting and you don’t absolutely need a car, I recommend not renting one.

NYC is denser–it’s usually an easy walk to the train. In Chicago, visiting some neighborhoods, buses will be involved.

In Chicago a car is unnecessary; in Manhattan, it’s an albatross. I lived as an adult in Manhattan for seven years, and never owned a car. When I drove to visit my parents in Queens, and wanted to go to the city, I took the subway in, and left my car at my parents’ house.

I rarely even took a cab in Manhattan. Vet appointments, and buying very large objects, like TVs, back when they weighed 50lbs were cab occasions.