To begin this review, I want to make note that I think honesty is important for helping others make smart decisions on where to stay when they travel -- as a parent, I especially rely on the honesty of past guests and always use reviews to help me choose a place where my family will be happy and comfortable as we travel. That said, this is NOT meant to be a negative review-- Ross's apartment in Wicker Park is very nice and ideally located if you are interested in exploring the city and want to have your home base in the best neighborhood in Chicago! However, while Ross's apartment is in an excellent location if you are unencumbered with baby/toddler things, it is not some place I would stay again as a family. There is an elevator in the building, and it does open up directly in front of the door to the apartment, but this elevator services the garage and there is no access from the front door. To access the garage from the alley, you need to a) walk down the alley, which is often littered with gross city things, b) open three heavy doors between the alley and the elevator, all of which require you to insert and turn the key (not always easy when you're holding a toddler's hand and likely other things as well), and c) these doors all lock behind you unless you physically prop them open. There is no parking directly in front of the apartment building because it is reserved as a loading zone for the dry cleaners downstairs, and there is not even an awning over the front door so god help you if you arrive in a rainstorm and have to park a block away like we did. Finally, the stairs to the unit are VERY steep, so steep that our very physically capable 2 year old had trouble with them, and we ended up carrying her up and down each time. If you aren't prepared or capable of walking up three sets of steep stairs, ask specifically for directions on accessing the elevator because we had to figure it out on our own. Located on a busy corner, this also means that it's close to many amenities like a grocery store, Target, boutiques, and many coffee shops, restaurants and bars. As for the inside of the apartment, it was perfectly comfortable for a short weekend stay. My husband was able to set up comfortably at the table in the kitchen and work, and my daughter loved having Disney + on the TV! The beds were super comfortable, but we had to hang a blanket over the window in the smaller bedroom so that it was dark enough for my daughter to nap. If you need a dark room to sleep in, just note that the curtains are either sheer or don't cover the entire window. Looking around, I felt that the entire place could use a little TLC -- a fresh coat of paint, some more thoughtful touches/artwork on blank walls, and the bath/hand towels seem like they've been around for quite a while. One of the things that drew me to this listing was the rooftop, but when we tried to access the roof the key wouldn't work as described in the manual. I never followed up with Ross about this because it was the morning that we were leaving and we just tried to pop up quickly before we left, but if you are set on using the rooftop I'd get clear directions first. A couple of concerns arose early in our stay and Ross was prompt about getting them cleared up, and at one point my husband and daughter were locked out and he got the door open for them right away, so I definitely appreciate his responsiveness as a host. I just think the space would benefit from a makeover to get it back up to the prime condition it likely started in.
So to sum it up: Would certainly stay again if my husband and I return to the city for a kid-free weekend, but likely would not stay again with our daughter just for the inconvenience of getting in/out of the condo.