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When my grandmother was still alive and would come visit me in Chicago, we always took in a Second City show, which, despite the handful of “oh my”s and “oh fa goodness”s, she always enjoyed. Her other favorite was the aquarium, which we zipped around like VIPs and sat in every first row with arrangement of a wheelchair for her. Probably too early for ZooLights at Lincoln Park Zoo, but definitely coming up. Their Fall Fest program might still be running.
The Music Box does a sound of music singalong during the holidays.
They do White Christmas as well
Lion King is enjoyable for all ages. Lots of other theater depending on her tastes. Check out Broadway in Chicago. Also look at the Chicago Opera and Symphony websites for upcoming shows.
If she likes comedy, Second City is usually fun and fairly clean for improv and sketch. IO theater is another option but think Second City is a better choice.
Check out Goodman theatre!
Rising Star
Twilight in concert so she can finally decide whether she's team Edward or team Jacob. Just kidding... I know she picked a team 20 years ago. On an actual serious note, if she's a Neil Diamond fan, A beautiful noise is coming back next month and was pretty solid. I'm a fan of Teatro ZinZanni if she isn't thrown by a little drag. It's dinner and also a little bit interactive. I'd maybe focus on whether she's going with friends or her daughters as I suspect she'll want something that they will enjoy too. Chicago has a ton to offer, I'm sure you can find something. I used to use Goldstar a lot for inspiration and sometimes cheaper tickets. Seems like it is called TodayTix now.
“High tea around town”
I’m not sure what this is, but it did remind me of the tea service at The Drake, which is a fun can-say-you-did-it kind of experience, if they might be interested in that kind of thing