What to do in Chicago?

Up here away from my girlfriend. Over drinking every night from college, and I’ve had a history of messing up as a bf and I want to do right by her. Not any friends up here either. All I’ve done in my little free time is go workout and play video games. What could I be doing to make myself more prestigious?

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this is pretty topical, I was about to post a question about this too. I'm visiting with my gf in a couple months for a weekend, neither of us have been there for like 8+ years. What are some other things you recommend?

Also, do you know of any architecture tours or anything like that? That sounds pretty interesting, I'm a big fan of urban design and Chicago was pivotal in that.

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There is an architecture tour on a boat that is pretty cool - takes you up and down the Chicago River and into Lake Michigan a bit.

My standard Chicago tour guide playbook is something like that, plus some combination of: 

  • Museums: Shedd/Field/Adler - walk around Museum Campus too if the weather is nice, great views. Northerly Island is now done(ish?) too and is a bit of a nice hidden nature walk. I saw a fox there once (ok maybe it was a coyote but whatever).
  • Beach / lakefront if it's nice
  • River walk
  • Bean pics / Maggie Daley park putt putt
  • Mag mile
  • Chinatown
  • Whatever restaurant they heard about in West Loop
  • Cubs game/Wrigleyville outing, even though I don't like the cubs 
  • Walk around interesting neighborhoods (wicker/bucktown, LP, river north, west loop). Usually more of a fallback if they've been a couple times or used to live here. Exploring Uchicago/NW and the botanical gardens also fits here.
 

Sounds like you need to make some friends, which isn't super straightforward as an adult. Basically you either need to come across the same people repeatedly (work is easiest, but not always a good fit; rec league - second that idea) or have some sort of shared hobby / activity (I've met a fair amount of people in my neighborhood just walking my dog/taking him to the park). 

 

Was going to joke with some snarky comment about chicago vs nyc but reality is that both scenarios would yield the same issues. The best solution is really finding friends whether it's through work or through a class or club or league or something. The solutions such as going to the museums and exploring places are realistically fleeting and more experiential if you're doing them alone. Make a commitment to yourself to find and make friends because once you have a couple, your circle will automatically widen and you will feel much more at home with a sudden ability to find things to do around the city. Know it's easier said than done but imo it's the only sustainable way to answer the "finding a way to do something" question.

 

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