Location. Location. Location. Everywhere we had planned to visit was a 30-minute walk or less -- Millenium Park & The Art Institute, Lincoln Park, the architectural river tour, Magnificent Mile, Riverfront walkway, grocery stores. Plenty of restaurants. We even walked from and to Union Station. Of course, there are also buses and the L close by.
The speakeasy is an interesting and quirky place to stay. This is not an upscale, luxury hotel. Be aware that you will carry your luggage up at least two flights of stairs, three if you're on the top floor. There is no elevator. This is an old building. No problem for us, just putting it out there for information. The kitchen is shared with all guests but no one was using it while we were there except to make coffee.
Our room was on the top floor and had lots of natural light. It was quiet and you couldn't hear the city below, which was nice for sleeping. The bed was comfy and the a/c was good for such an old building.