Sadly, the stained glass museum that @wis75 mentions is now closed. http://www.driehausmuseum.org/about/view/navy_pier I second @2VU0609 with the Driehaus Museum (see link) if you like period architecture and furnishings. It’s in the Michigan Ave area recommended for hotel - you may also see that area referred to as “River North”.
If you want to go on the Architecture Boat Tour, you may need to book in advance. Very popular in summer.
If you do the river architecture tour, book for an early time. It’s 90 minutes long and you are on the top deck in the sun if you want to hear the docent detail the buildings and if you want to see well. You can retreat to lower level for bathroom and drinks, but I wouldn’t want to spend the whole time there. We were supposed to do it at 10 am, but were out and about early and they let us exchange tickets for a 9:30 tour. Not sure if that’s the earliest option.
When I posted our picture on FB with Wrigley Building in background (but no written location), my feed lit up with responses of friends who had also done the tour raving about how it was their favorite Chicago adventure on a good day.
The Chicago Public Library was fascinating with its gargoyles. It even had a 3D print too but I’m not sure whether they git grant funding to keep it open. We were in The city for a week so we’re able to do more.
If it is within your likes, the museum of science and industry is kind of cool (went there many years ago when checking out the U of Chicago), it is I believe the only building left from the 1893 White City at the Columbian exposition. Has a lot of neat displays, they also have things like a U boat from WWII.
If you like and are considering museums, I would advise taking a look at the websites for the “majors” - Art Institute, Field Museum, Shedd Aquarium (above posts about crowds is very accurate), Museum of Science and Industry, Adler Planetarium. All are world class and some may appeal to your personal interests more than others. Field, Shedd and Planetarium are on one campus, broadly defined, ie, walkable between them. Art Institute is closest to the Michigan Ave/Loop areas. If you plan to stop in there, I suggest looking at an on-line map and determining where you want to spend your time. Some of the maps show where the collection highlights are located.
If you do the architecture boat tour, make sure it’s the one by the Chicago Architecture Foundation. They also have some interesting walking tours. For my money, the best things about Chicago are the Art Institute, the architecture, the food, the neighborhoods, the blues, and the Cubs.
Thank you all for great suggestions! I am making a list with all suggested ideas and will sort out which to fit in to a day visit.
I’ve been to the Shedd Aquarium twice in the last two weeks, taking advantage of the free days for Illinois residents. It’s great if you buy your tickets online and you are waiting in line when it opens. If you can’t be there at 9 am, do something else; the crowds are intolerable.
“If you do the architecture boat tour, make sure it’s the one by the Chicago Architecture Foundation.”
This is my go-to answer for what to do with one afternoon in Chicago, which is a more common situation than I would have thought. People come in for a meeting or convention and can only sneak away for a few hours.
We went in early evening and it was a lovely boat tour. If you go, do bring a jacket it can get quite breezy by the end of middle to the end of the tour. The kid in tshirts and shorts in our tour was very cold by the time we docked.
I also just did one day, June 1. Amazing city, a gem. Great people. Can’t believe I never visited before.
I took the Hop On Hop Off tour, which I found worth it for the quick overview of the city itself. It goes past all the Must Sees, with some history (how accurate, no idea,) and you can get off at a stop, then hop back on later, for more in the circuit. This, rather than just selecting one or two spots and missing the holistic. It took me to the Hancock where I had a drink on the 95th, a 360 view. Yes to the ladies room for its view.
I also did the CCC, (the Chicago Cultural Center, the old library) and a few other stops. Walked a ton. So impressed.
I used Marriott points at the Renaissance Blackstone, on Michigan Ave. Had a room with a view from the Shedd to Navy Pier. Lake Michigan is spectacular.
Maybe someone can answer this: I had perfect weather. Someone joked it’s often overcast. Is that so?
Wildberry Pancakes for breakfast (across the street from the north end of Millennium Park) - go early because the lines really build up. Lou Mitchell’s is fun but out of the way unless you’re going to the Sears Tower (or whatever they call it now) or Amtrak station.
We went back to Chicago last year after moving away the year before; stayed at the then new Loews which was a great location. Some of the other hotels we’ve done staycations at include The Palmer House, Embassy Suites Mag Mile, Homewood Suites Downtown, and once the Intercontinental which has the most indoor wonderful pool.
My top re-visits were the Art Institute and Millennium Park; also wanted to see the Riverwalk which was in process when I was last there.