[Avista]

My daughter, granddaughter (17) and I are planning a girls trip to Chicago this July. Any advise what to do or where to stay would be appreciated. We're thinking of Airb&b near the Water tower or Loop. Any thoughts?
Will be flying into Midway. I read where we take Orange train into town. How and where do we pick it up? I will have carry on and small suitcase so am a little concerned about getting to where we will stay from airport.

I was in school in Chicago, but that was 55 years ago lol. At that time dorm was between water tower and lake on Pearson.

Thanks for any help offered.