Ha, I live in Chicago! How long are you stopping by for? If you need any food recommendations, let me know. And I'm jealous of all your other stops. I've been dying to go on a road trip recently, but it's kind of hard between work and not having a car.
We'll be in Chicago and the surrounding area for two days and two nights. I know we're doing Yolk one day and stopping by some of the breweries such as Mad Mouse and Hopothesis, any recommendations are very welcome! It's a moving road trip whoooooooooo, all I'm hoping for is good weather and for my car to make the trip.
There's also Revolution Brewery, they just opened their tap room recently. There's also the Goose Island brewery/pub but it's kinda touristy. Once you're going west I recommend stopping off at Two Brothers either location shouldn't be too far out of the way and the food and beer are amazing. Just a warning though, they can get super crowded, especially around happy hour. It's a toss up between Little Goat and Bacon n Eggs for my favorite brunch place in the city, but I know Yolk seems up keep opening up new locations, so they must be doing something right. I wish you luck on your move and hope it's as enjoyable as possible!