Skip to main content
Beginning of main content

Old Chicago Inn

2.0 out of 5.0

Recent guest reviews

This was my first B&B experience, and it was awesome! David, the staff member, was super friendly, helpful, considerate and a delight to be around... we chatted for a few hours, and he entertained me with stories from his youth and characters from his neighborhood. I felt like I was a guest in the house of a friend. I had the first-floor room, and they accommodated a late arrival, and checked my bags for me when I left but was gone all day, that was appreciated. The breakfast was good, and the speakeasy downstairs was fun! Great experience, highly recommended! Very convenient to restaurants, bus line and entertainment in a vibrant neighborhood.

My collegue and I go to this Old Chicago almost every wedk for lunch. The pizza is amazing, if you get a chance to try tgd Lasagne pizza, it’s incredible. The service is usually top notch and our favorite waitress is Dana... she’s super great.

Very enjoyable lodging walking distance to Wrigley and close to the El. David the host was very accommodating and pleasant. The downstairs ‘speak easy’ was a special treat with outstanding drinks concocted by a talented mixologist, whose name slips me. White Sox’s stadium was fantastic especially since our Tribe won! Chicago is fun!!!

Our room was very small and dark, but at least we had our own bathroom in the hallway. The rooms on the third floor also come with a common living/sitting area, which kind of made up for the small room size. Breakfast was pretty basic, with pastries, orange juice, yogurt, fruit, coffee. The main attraction of this hotel is the décor and furnishings, which match the period of the building itself. The huge positive was the location of the hotel, which is only about a block from the transit station for trains going into downtown. Also, parking is free on the street, as the hotel gives you a parking sticker to avoid getting tickets.

A perfect place in Chicago if you like historic places with nostalgia! Excellent breakfast and service. It is an old house with smaller rooms and in some cases shared bathrooms. A fabulous speakeasy at night in the basement with amazing drinks. A fun restaurant/bar just down the street both owned by the same people. We received vouchers at the restaurant for staying at the Inn. We attended a concert at the Aragon, a game a Wrigley and a concert at Soldier Field when we were there. It is located conveniently by a train station and a famous Chicago pizzeria just down and around the block.

My husband and I have stayed here twice for family events in Chicago. The rooms are small and old but clean and comfortable. Some have bathrooms in the rooms, some baths are in the hall. Very good continental breakfast. $10 per guest coupon for bar/grill next door. Weekends they open an old speak-easy bar in basement. Close to trains. Steep stairs. Host was very nice and helpful.

If you're one of those who enjoys services at your feet of major hotel brands, this isn't for you. If you enjoy stepping into a charming, older guest house, right in the middle of a great neighborhood, then this is for you. The interior decoration is lovely - it's a step back in time. Neat posters, furnishings, and decor. The rooms are basic - but the beds are comfy and clean (not a lot of natural light where we were, though, but it was ok for our needs). Location was fantastic - close to Wrigleyville, Boystown, and all the great "local" spots - right by the Belmont CTA stop. Were very pleasantly surprised by the breakfast in the morning. Assortment of juices, tea, coffee, yogurt, some fruit, and some very nice, homemade selections. Honestly - great bread pudding. Just to note - stairs!! Be prepared to carry your bags. If you need an elevator or can't live without one (you poor thing!) then just don't. Only other downside is that concessions can be hard to come by - so get your bottled water, other beverages, or snacks at Walgreen's down the street, or trek down to the 7/11. It also can be noisy with other people coming and going, so if you're a light sleeper, this might bother you. I would definitely be back. Charmed 100% by this place.

The Old Chicago Inn is, well, kinda old. But that's not a bad thing, as it's full of character and in a great spot. It's super close to the trains, and within walking distance of a number of restaurants and other spots. The owners were super friendly and helpful in terms of recommendations, some of which we tried and enjoyed. The rooms are very small, and most have a bathroom outside of your room. We happened to stay in one of the rooms where we had an attached bathroom, which was convenient. We did not check out the speakeasy at night, though did enjoy the continental breakfast there. There was good coffee and tea, along with fruit, danish, etc. Pretty standard. Two negatives regarding our stay. One, being an old building, the walls are super thin. I'm not a fan of being able to hear someone wake up and use the restroom in the middle of the night. The second was not a major deal, but there were heating issues the weekend we stayed there. They were on top of it, however, and provided electric heaters to everyone to make sure no one was cold. That worked fine. So, I would recommend it, just know that this is not a cookie cutter chain hotel where everything is shiny and new.

We stayed 4 nights here, loved the décor and old time feel of the inn. We had a fireplace in our room, which was very nice to have. This place is full of period antiques, and the décor is art deco style, giving a feel of old Chicago. The staff was very helpful and knowledgeable about local sights and restaurants. We did go to the speakeasy in the basement. It was done up in authentic prohibition era décor, and they served cocktails from original period recipes! They also had live entertainment, a piano player who was very good. The bed in our room, 2A, was surprisingly comfortable. It was awesome to be able to fall asleep every night to a live fire in the fireplace. We would certainly return to this inn on our next visit to the Windy City!

We booked room 1C based upon the info and picture posted on Old Chicago Inn’s website What a mistake! Talk about misleading! The image posted has a cozy room with clean carpet, paint, etc. (see attached image with nice brown plaid comforter on bed). The real room 1C has paint that is chipping, carpet so dirty that we never took our shoes off, a old worn out chair and a bed that is not comfortable (see remaining attached images). I emailed Virginia, the owner about 1) the false advertising on her website and 2) the poor condition of the room. Her response was offering a 50% discount on the room, which I accepted. She never mentioned the false advertising on the website. Needless to say, will not stay here again.

3222 N Sheffield Ave Chicago IL

Hotel highlights

  • Walking distance to Vic Theatre and Wrigley Field
  • Free continental breakfast
  • Free WiFi in rooms and public areas
  • Free parking

Located in Lakeview, Old Chicago Inn is adjacent to Vic Theatre and within a 10-minute walk of other popular attractions like Briar Street Theatre. This 10-room bed & breakfast has free breakfast along with conveniences like free in-room WiFi and free self parking.


Free continental breakfast is included with your stay.


A TV comes with satellite channels, and guests can stay connected with free WiFi. The pillowtop bed provides a full night's sleep and the bathroom offers bathrobes.

Property features

Guests of Old Chicago Inn enjoy free WiFi in public areas, a meeting room, and laundry facilities. You can take advantage of free parking if you drive. Dry cleaning/laundry services make packing light an option. This bed & breakfast also has a fireplace in the lobby.

Room options

1C - Full bed, Private bath across the hall

Full 1 | Sleeps 2

2A - Queen bed, Shared Bath

Queen 1 | Sleeps 2

2D - Full bed, Private Bath

Full 1 | Sleeps 2

2E - Full bed, Private Bath

Full 1 | Sleeps 2

Reviews from Trip Advisor

Trip Advisor aggregated rating

71.0% of guests recommend this hotel

Total of 122 reviews