There's only one thing that makes the Old Chicago Inn tower above probably every other B&B in Chicago and far surroundings and its name is Jon.
Once you've got used to his endless stream of ideas, hints, advices, encouragements, etc. and let it all sink in, you realise (and experience later on) what a priceless guy this innkeeper is. Tell him, for instance, that you intend to visit the Chicago Zoo and are looking for a place to have lunch afterwards and he'll instantly come up with the name of a gem you otherwise wouldn't have found in a million years. Plus a detailed story about its origin and a why the interior looked the way it did.
(And yes, Jon, I bought the R.J. Grunts' T-shirt!)

It's just one example of the many precious suggestions that made our visit to Chicago extra valuable. On the last day of our stay Jon had a day off and guess what: the Old Chicago Inn turned into just another B&B, good but nothing extraordinary.

Picked this hotel after research on Trip Advisor and I am so glad that we did. It was definitely a unique place to stay. A lot of the rooms do not have bathrooms in them but one will be assigned to you. It is clear on their website which rooms do have the bathrooms and which do not. We went with one that did although it was a little different. The "bathroom" was really a toilet in the shower stall with a sink behind the bed. While a little strange I loved it. Very good use of the small space. The room was exactly what you need with one of the comfiest beds around. Here are a few bullet points:

The staff and hotel - Very friendly staff willing to help anyway they can. Upon check in you will be given a 10 dollar coupon for each member in your party for food at Trader Todd's next door. You also will get free access to a gym next door and wi-fi access. There is also a kitchen upstairs where you can store leftovers and warm them up. It is an old house so the floor will squeak and the walls are thin and there might be a little leakage in the shower but it is absolutely worth it to be in the area and have the experience of something other than the same old hotel you are used to.

Parking - Is free with a parking pass that is given at check in. However, it is street parking so you might have to park a little far away from the hotel.

The area - Great area. There is a TON of shops, restaurants and bars within walking distance. The train is about a block up and a hop on it or a bus will get you to almost anywhere you want to go. You can walk to Wrigley as well although we took the train and it is only one stop up.

Overall a great trip and we can not wait to go back.

We stayed in the smallest room, 2C. It was comfortable for 2, and we werent in Chicago to sit in our room anyways. The room has a shared bathroom and we never had to wait even though the Inn was full. Breakfast is a standard continental like breakfast that would be found at any hotel. The Inn also has a full size guest kitchen. The kitchen is more for storing food and warming up leftovers as opposed to cooking, as it doesnt have any utensils or anything in it. The Old Chicago Inn has a great location, just a short walk to Wrigley Field, the train station and lake Michigan. The free coupons for Trader Toms next door is also a plus. You could easily stay on a budget by eating breakfast at the Inn and a big lunch practically for free next door at Trader Toms. We loved Chicago and will be back.

We stayed at the Old Chicago Inn with family from Europe while showing them Chicago. We decided to stay at the Old Chicago Inn and not at a chain hotel because we wanted to offer our relatives a unique experience. This plan backfired. The bathroom had black mold growing in the shower and on the window sill. Of the three light bulbs above the sink in the bathroom one was burned out and one totally missing. The room was dusty and it was very loud at night. Also, we had to look for the manager to check in at a bar two doors down. All this would not have been a big deal for us if the price would have been half or a third of what we paid. For the same price I could have stayed at the Hilton Double Tree downtown where I have experienced excellent service before and I regret that we did not do that. You do not get what you pay for at the Old Chicago Inn.