We live about 65 miles west of Chicago.
Here are a few suggestions of our favorite places.
The aquarium is truly wonderful. While my daughters were skating in Chicago (seven years), my husband maintained a membership, and he visited the aquarium every week. Right now, for $200, you can swim with Beluga whales! If you like this idea, I would suggest finding a website and making advance arrangements–I’m sure there’s a huge waiting list.
Right now, there’s a Harry Potter exhibit at the Museum of Science and Industry, but it ends Sept. 27. My husband and our daughters saw it. My husband, to be honest, wasn’t impressed with the Sci and Ind Museum–it’s changed over the years and now it’s more of a children’s museum, but the “hands-on” activities are incredibly dumbed down and kind of stupid. HOWEVER–GO SEE THE COLLEEN MOORE FAIRY CASTLE!! Here’s a link:
msichicago.org/whats-here/exhibits/fairycastle/
Even my cynical 20-something daughters were bowled over by the Fairy Castle–it’s so cool! Little lights that really work, etc. Very fun.
I personally like the Field Museum, but mainly for the mummies. Also, the lions that ate people in Africa are stuffed and on display. It’s an older museum.
Go see the Bean–it’s in Millennium Park. It sounds dumb, but it’s sooooo cool. Prepare to sit and watch people!
If you don’t already have a store like it in the big city nearest your home, then go to the American Girl Place on Michigan Ave. It sounds like a big commercial tourist trap, but it’s really, truly fun. You don’t have to spend a thousand dollars (although you might be tempted!). You can spend six bucks and buy one of the mystery books. Or you can just sit in one of the comfy chairs and read it there for free. There’s a tea room and a play, too–one of the girls in our parish played “Samantha” for several years (until she grew too old!)
Gino’s East is the place to go for pan pizza, but oh, my goodness, it’s filling! Do not overeat. Bring a white pen–there’s graffitti everywhere, and you will want to add to it.
I personally like Ed Debevic’s–great old-fashioned homestyle food (e.g., meat loaf and mashed potatoes, chicken fried steak, even liver and onions), and the wait staff is purposely sassy. Don’t go there if you want to be left alone-they pick on everybody! Order the corn–it’s really good–I think it’s one half corn and one half butter, with about three tablespoons of salt!.
If you like Molten Chocolate Cake (they serve it at Chile’s Restaurants), there’s a restaurant in Chicago that originated this dessert. I can’t remember the name of it, but I’ll ask my daughter and get back to you on this thread. Warning–bring a novel to read (all the way through) while you’re in the line–it stretches out. There’s probably times when it’s not so long, but I don’t know those times.
IF you are in the Western Suburbs (it’s possible, depending on your business), visit the ice rinks in Rolling Meadows. (Just ask–there’s an old rink and a new rink.) This is the home of the Chicago Jazz, one of the best synchronized skating teams in the world. If you go on Saturday morning, they’re practicing (at the new rink). The practices are generally closed, but if you look up my name on the website in my signature, and tell them that you know me, they’ll probably let you watch, and if Pat’s there, they’ll probably give you breakfast or lunch! Stunning, beautiful skating. Like I said, it’s not exactly tourist stuff, but I can guarantee that you won’t be able to watch the Chicago Jazz practice anywhere else in the world!
Another thing you can do, although I’m not sure if you’re interested–is go on one of the Chicago “haunted tours.” There are several of them in Chicago in October–mostly just for fun. Not everyone likes this, I know.
I guess if I were going to visit a church in Chicago, I would go to the Mission at Our Lady of the Angels–here is a website link:
ourladyoftheangelsmission.com/
This is the site of that horrible fire in 1958, and now a mission has been built. Father Benedict Groeschel is one of the founders. I think that a visit to this place would be very meaningful, like a mini-pilgrimage–a chance to remember and pray for the souls of the nearly 100 children and sisters who were killed in that fire. When I was a little girl, my mother would tell me about the brave sisters who tried to protect the children–and my mother and father weren’t even Catholic! The fire also brought about safety changes in schools all over the United States.
If you want to go a little further north, Marytown is in Libertyville (a wealthy suburb). Marytown is the National Shrine to St. Maximillian Kolbe. Absolutely nothing fancy–your own church is probably prettier. But it’s a holy place, very restorative. My husband and I really enjoyed our day there. If you want lunch at the shrine, you have to arrange it in advance.
I hope you have fun! Wish I could go, too!
It’s still up in the air, as travel restrictions change a lot in my company, but this could be a really great trip, if I plan the offtime right! Thanks for the ideas, Paul.
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Looking at the postings of those church pics, I realize how Florida lacks traditional church architecture. Norseman, those church pics are nothing short of breathtaking. I might have to grab some pizza, and go for a church tour instead. 
I mean, really?