re: Chicago, things to do?

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We fly into CHI on Thurs around 11am

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Are you flying into MDW or ORD? In theory, traffic shouldn't be terrible around the lunch hour, so you could take Lyft/Uber. Otherwise, the cheaper option would be taking the Orange Line from MDW or Blue Line from ORD and transferring to Red Line. Not as difficult as it seems and it'll take 45-60 minutes.

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and have reservations at Girl and the Goat at 9pm...looking to see what you think we should squeeze in.

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Take the Red Line or Lyft/Uber to Pequod's before 3:00pm and get their lunch special, which is $4.95 personal pan pizza.

If weather cooperates (30s/40s and clear), walk off the grease and head east towards the Lincoln Park Zoo. DePaul is on the way and they have a nice campus. The Zoo is right on South Pond and you can get unobstructed views of downtown.

Head to West Loop a couple hours before your Girl and the Goat Reservation and grab a few drinks. Booze Box and Izakaya at Momotaro are subterranean lounges with great cocktails. Blind Barber will have a young professional crowd with "speakeasy" vibes. Lone Wolf is a dimly-lit tavern that makes good cocktails. Ballast Point has a taproom in the area. CH Distillery is just east of the interstate.

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We have tickets to the Blackhawks game the Friday night at 6:30, but outside of that we are wide open....

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We don't fly out until Sunday afternoon at 7:00pm so we get 3/4 of a day on Sunday as well.

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CityPASS gives you access to Shedd Aquarium, Skydeck, Field Museum, Adler, and Museum of Science and Industry. You don't have to knock them out in one day, or even go to all, but you can spread them out on Friday, Saturday and Sunday.

Downtown is fine, but Chicago is a neighborhood-centric city.

- Head to Chinatown and eat lunch at Go4Food.
- Southport Corridor is a great street in Lakeview with boutique shops and restaurants. My go-to is Corridor - they brew awesome beer.
- Wicker Park is an eclectic neighborhood with plenty of [harmless] weirdos and young professionals. Grab an evening cocktail at Up & Up, which is the rooftop at The Robey. Incredible view. Stop at Violet Hour afterwards. - Logan Square, like Lincoln Park, is very family-focused, but has some of the best cocktail bars and restaurants in the city. My two favorite restaurants there are Fat Rice and Giant. Couple cocktail places are The Whistler, Lost Lake and Spilt Milk.
- Loyola and Northwestern aren't far from one another. Both have beautiful campuses and accessible via Purple/Red Line.
- I've gotten to know Pilsen more-and-more over the last several months. Some good food spots down there. I would recommend Taqueria Los Comales for Mexican and Pleasant House Pub for a cozy, British-inspired setting. Moody Tongue is right near there. They have a couple good barrel-aged beers available.

Not sure if the above is what you were looking for, but let me know what else you had in mind.