Chicago → Chicago Bachelor Party Weekend

Next weekend I'll be in a group of 8 guys going to Chicago for a bachelor party. We're taken the 1st train from STL and will be in town around noon on Friday. We'll be staying at the Wyndham Grand Chicago Riverfront. Other than the groom saying Chicago has an awesome nightlife, we have no idea what to do. I feel like this will turn into an expensive drunken weekend without any prior plans. We'd like to stay semi close to the hotel. Uber, L and walking will be our transportation. Anybody have any ideas?

Not sure how old your group is or what you like to do, but weather permitting I'd head over to Oak Street Beach.

If you have a big enough group you might want to check out »theescapegamechicago.com/ it's a lot of fun.

Visit a local brewery.

Bribe a local politician.

Keep one eye over your shoulder, even before sunset.

Bring a bullet proof vest, some quick clot, and a fire arm. (just kidding)

STAY AWAY from the West and South sides.

We had a pretty good time. Lots of walking, L riding and Uber trips. We made it to Tavern at the Park, Stout Bottle Room, Chicago Blarney Stone, Howells and Hood, Rock Bottom, Sheffield's Beer Garden, Harry Caray's along with a few others that I cant remember. We of course finished Sat night off with a trip to VIP's. Friday night ended with a view of the sunrise over Lake Michigan in an Uber. We didn't have any crime issues but we stayed downtown for the most part.

Damn, you guys did it right. Glad you had a good time. Sounds like you maximized your time here alright. Out of curiosity, what were the ages of people?

30-32. We could've done a bit more but we didn't go with a plan. Wandering around took up quite a bit of time. We did figure out you can go to the top of Hancock for "free." Just go up to the bar instead and buy a drink.