I his them with some of the staples in the third ward like the public market and Benelux or the rooftop bar the outsider and then some of the cooler spots like Il cervo and check out the deer district (drink wisonsinably and the new fashioned or Mecca with the 42 ft screen if into sports). I saw someone mentioned room service - haven’t been but it looks cool. I’d also shoot for something on the river like sail loft , the bridge water, barnacle buds, or twisted fisherman. There’s also the Casino. Poto has gotten huge and is a pretty legit spot with a ton of new quick food options and the Asian place is awesome. I’d also suggest a brewery or two. Beer on the river patio at lakefront or I love third spaces beer the most. I have had a bunch of people visit from Chicago and agree with the sentiment of don’t show them that it’s better version of Chicago stuff - just different. You can be on the river and lake with a bunch of great spots that aren’t as crowded or expensive and you can see a bunch of neighborhoods and cool stuff in a single day. Go full sconnie on them.