Have you tried Hooters? I have a friend there and she says that's a great place to meet people at. But then she works there so she might be prejudice.
I hope I can find friends in Chicago. I am moving there shortly.
You've GOT to be kidding! Chicago is and is known the world over as a friendly town! And, Especially for someone your age! Be brave, go out, hear live music, mingle, talk to people...... There are so many opportunities here to be active and to meet others. Good luck.
I wish that I could help. I live in a small town, same town my entire life, and I cannot make new friends..strange..I know that it is hard. If I lived in Chicago, I would be your friend
Mingle Around Chicago (website)
Its true...chicagoans in general do not know how to keep a simple conversation.
Try the airport
I think you need to get a face. Chicagoans don't care for faceless folks.
I've been in Baltimore for over 20 years, and have very, very few friends. I know that Baltimore is a hick town compared to Chicago, so maybe it's just a new town thing...I don't know, sorry.
The key in Chicago is to never look anyone directly in the eye. That actually might be New York, but I've found it's a pretty good rule everywhere.
Feistylittleminx lives in Chicago
Most people are like this in big cities.
Don't make eye contact with anyone.
From the city or a suburb?
There is a group in Meetup called "New Bar Meet Friends Every Two Weeks". It's mostly 20s and 30s and they go to a new bar every two weeks in Chicago. I've been there several times and it's a lot of fun. Met some of my new friends there.