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What does your toddler like? I used to take my toddler to Shedd to see the fish, on train/bus rides to let them see a lot more people than they’re used to, but that depends on if your toddler is good with things like that :)
If you want to go out of Chicago, we did a day trip to the kids museum at Rockford- it’s definitely toddler friendly!
Wisconsin Dells?
Maybe go to Milwaukee on the Amtrak?
Downtown and hit up the Shedd or the Lincoln Park Zoo?
Nature museum especially if the weather is bad. There’s an indoor play space