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Apartments.com... Realtor.com... Call a realtor if you want to understand condos for rent too.
Pro
Apartments .com and Zillow. Do a first round of searching to find your top 2-3 neighborhoods, then look at what’s around you (good restaurants, bars, record shops etc), then double click on your top 2-3 neighborhoods on those sites. Typically renting from a condo owner gets you a much cooler spot than from a big company but condos can be slim pickings in certain neighborhoods. I highly recommend starting with Lincoln Park, Wicker Park and West Loop - very different vibes from each hood, but gotta say don’t underestimate the value living close to Lincoln Park/Lake Michigan
can bring - it’s a beautiful place to take walks around all year round. Good luck and welcome
I also love love love my neighborhood (near north)