Considering moving to Chicago

Me and my wife currently live in Frisco, TX. Thinking about moving to Chicago at the beginning of May. Have a dog. Mostly want to get out of Texas because of heat, lack of good places to walk with dog and frankly speaking, Dallas is dead in terms of activities

We are going to visit Chicago this Feb/March just to look around, visit some apartments and make some choices.

Ideally we are looking to a 2bd or 1bd + den apartment(but considering other options too), near some green(to walk with a dog). The neighbourhood should be safe(that's important). Would be great to have a washer(dryer?) in the apt(but that not really very important). We are ready to pay sub $3-3.5k. May be higher, if the candidate is ideal. We are working remote - 5 days at home. Parking garage would be great, we have a car and I want to sleep calm. Not VERY far from the downtown, I don't really want to have a 1hour car drive at weekends at one end just to be in center of all activities.

I don't care about pool, gym, bbq and all other stuff. We have all of that here in Frisco and I'm not really using it much

So my questions are:

  1. Where should I originate my searches(currently I'm going into random reddit posts, and look at different apts from there) - is there any aggregator, or it's better to individually pick and search through all the options we get

  2. Which areas we should focus on? I heard about Lincoln Park, Gold Coast, Lake View, Lincoln Square, Ravenswood, Evanston. More "hipsterish" options like Logan Square, Wicker Part, Bucktown. Those recommendations I received from my friend, so not sure whether they are too accurate

3.Besides from the 1. question, my friend also told me that you can rent directly from the owner(as he does). It might be cheaper, but I'm not sure where to look into that. We moved from Europe(Poland) and there it was the only option, you are going to an aggregator - then meet the owner and discuss everything. How do I search such options here?

  1. Of course, if you have some building complex in mind - please, post in comments, would appreciate that