Love, love, love Chicago -- DH worked there for a year when we were dating and our oldest is in grad school there now. Definitely do the Architectural Foundation boat tour, bike along the lake, visit the Art Institute, and try to see a show at Old Town School of Folk Music. Marriott Downtown Magnificent Mile is well-located and generic. The Hoxton in Fulton Market neighborhood is great. My favorite restaurants are Virtue in Hyde Park (near University of Chicago campus) and Gather in Lincoln Square (try to get a table in the garden). For a bit of a field trip -- and maybe also a tour of Northwestern -- head up to Evanston and have dinner at Taco Diablo. Or, even more of a field trip, go to Indiana Dunes National Park -- about an hour drive.

Anonymous wrote:OP here. I think we decided to stay at an Airbnb in Lincoln Park, near the zoo (corner of Clark & Wrightwood, according to the description). I thunk being near the water is attractive, as that seems to be where most of the action is.

Another option was a super nice place in Wicker Park but I think that's too far away. But it does look super, super nice.

Wicker Park is much nicer and you’re about the same distance from the Loop.

OP here. I think we decided to stay at an Airbnb in Lincoln Park, near the zoo (corner of Clark & Wrightwood, according to the description). I thunk being near the water is attractive, as that seems to be where most of the action is.

Another option was a super nice place in Wicker Park but I think that's too far away. But it does look super, super nice.

Enjoyed Wicker Park as well as a lot of other places mentioned above. I’ve always had a really good time in Chicago.

Chicagoan here. I agree - stay in a neighborhood. If you'd like to have restaurants and shopping at your fingertips and not be with tourists, check out Logan Square. The blue line El train makes it easy to get into the Loop. I like Wicker Park and Bucktown, too, but Logan Square is the current hot spot.

You may be able to find a Jazz show that permits under 21s for early shows. And if you do make it up to Evanston, see what's playing at Space, one of the very best (and SMALL) music venues in the city. The Old Town School of Folk music has great concerts, too, and would bring you into another great neighborhood - Lincoln Square.

As for dining, there is a ton of fabulous Mexican, especially on the casual end, both south and west of downtown. Folks focus on hot dogs and pizza and Michelin and miss so much.

Chicagoan here....I just did the Wrigley Field Tour with some out of town guests, it's awesome. They run when the Cubs aren't playing at home. All the other recommendations are good.

I'd also add to check out the Pilsen neighborhood, great food and fun to walk around.

Lastly, be aware there is a LOT going on this summer in Chicago including several music festivals and a NASCAR race right downtown. plan accordingly!