I'm in Chicago for a couple of days. We have a Cubs game Thursday and the draft Friday night. What would you recommend I do while here? Food, fun etc.
Hit a steakhouse before you leave. Make reservations at least a day in advance or you will wind up eating at one of the franchises and they're nowhere near as good as the standalones. I haven't been to Chicago in over a decade at this point but I always made it a point to eat a prime steak from one of the big standalones when I was there. You can't go wrong but you have to make reservations or there's no table at the inn when you get there.
Tavern on Rush. If the weather is nice and the windows are out its an awesome bar. Met Vince Vaughn there which was cool. Also met Jay Cutler and he was a douche. Best curry mussels I've ever had at a place called The Gage. We had an order of them and when we got done we said, "can you bring us another?" Great wine list too. _
Just remembered, we did a tour of Revolution Brewery. Was pretty cool-got a little knocked up. Also there are a few beer gardens across the street from Wrigley--if you go out the exit right about where home plate is and walk straight across the street, there are 2 or 3 right there. Last time I was there was for a day game, was a great scene after the game. Locals were pretty nice. _
Billy Goat Tavern on Lower Michigan. Rooftop seats across the street from Wrigley for a game. Kingston Mines, Rosas and/or Blues Chicago for some great blues.
Revel in the architecture downtown and in the magnificent mile- every building is different and amazing. Signature Lounge for an awesome view (if there is a line, it will usually move fast). Avec for dining- doesn't accept reservations. I personally love the Botanical Gardens, but they are a little bit of a drive, north of the city. The wiener's circle if you like shitty hotdogs served with abuse (youtube it). Don't eat deep dish pizza- it's shit, and don't go to the Southside.
Love the building with a stone from every state and from many countries across the world. We walked around that building for literally about an hour. So cool. About 3:25. So good. One time only, day game and during the summer. _
Tribune tower- very cool. And Stewart- Hahahaha- I remember that episode. Classic. "An above ground marinara swimming pool for rats." Genius.
Get some Bourbon County from Goose Island Brewery. You can get the Proprietor's Blend in CHI, they don't distribute that stuff anywhere outside of CHI.