Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
This is a single family home that was originally built and owned by a bootlegger during the prohibition period of the 1920's. He had a boat in nearby Belmont Harbor and would sail to Windsor Canada to pickup whiskey and then sell it from the backyard to locals. He was always on the lookout for cops. There is one remaining "escape door" in one of the bedrooms on the main level. We keep it locked, but it still works to get you outside fast.
Large enough to sleep 22 people with plenty of space to mix, mingle and play (including a foosball table). 2 car garage and outside pad for large vehicles. Awesome location in East Lakeview near Wrigley, Lincoln Park and more.
Over all a great place to stay if you want to see the city and all the attractions. The house was clean. The Foosball table needs some work missing a couple of screws, lots of board games for the kids but a lot of them were missing pieces and need to be thrown out.
This stay was a wow! Great neighborhood, off street parking, close to everything we wanted to do. Beautiful home with excellent furnishings and decor. Comfortable beds and quality linens. Nice kitchen.The living room with gas fireplace was so cozy. I would stay here again without hesitation.
We stayed here in January to visit some family and enjoy the city. The location of this place is amazing. its right downtown , very walkable to everything. The parking is great, with the 2 car garage it was heaven for being in the city. The property is so nice. Its massive. upstairs and downstairs ; with room for so many people. We ended up only have four people ; and just loved it. The living room is so cozy, with the fireplace and sofas, the property was perfect. Matches all the pictures. And the host communication was perfect. Highly recommend !
Flew into town with a large group for a bachelor party. Walked up to Wrigley for an afternoon game, easily took the train downtown and to/from ORD, had a lot of fun at the myriad bars and restaurants in the area. The host was very accommodating and gracious, I couldn't recommend this place any higher.
We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive.
We are a broadcasting team for the Democratic Convention. We could not have had a better place to stay after our long work days. The location for restaurants was
fantastic. The size and style of the house was on point. A good stay for the crew.
Stayed for a bachelor party. Nice neighborhood, short walk to wrigley with bars along the way to stop at. Only annoying thing was parking. While there is 3 spots (2 car garage, plus 1 on the small apron in front of the garage) you can not park more than 1 bigger vehicle there so we had to use the parking garage nearby. Luckily it was only 25/day.
This place was wonderful! It was so clean, had plenty of space for our group and had everything that we needed. Location was perfect! Even though we had a rental car, there was so much within walking distance. So many great restaurants. Having that garage to park in was the cherry on top!
Dear Will,
I wanted to take a moment to thank you for hosting us at your lovely property. We truly enjoyed our stayâyour place was comfortable, well-appointed, and had everything we needed to feel right at home. We also appreciated the prompt response and neatly arranged house for hosting our group of friends.
we would gladly stay here again in the future. Thanks once again for providing such a great space!
Best regards,
Abhi
Wonderful location, plenty of room, thoroughly enjoyed our stay! We were a group of 30-somethings in town for a weekend. Really enjoyed how close we were to the lake and to coffee shops, restaurants, and transit, but still on a quiet street. It was super convenient, really easy check in with door codes. We enjoyed the roof deck on one nice day, and overall had a great time. Lots of space for all of us! We would happily stay here again.
Amazing place to stay for a guys weekend at Wrigley! Plenty of space, multiple bedrooms equipped for a large group, great living room set-up for hanging/gathering.
Neighborhood is wonderful and easy to walk to several close restaurants and bars.
I would definitely stay here again.
This was an amazing house! Seemingly infinite beds and bedrooms, but still with spacious common areas. The neighborhood is wonderful--easy walk to the lake with lots of restaurants and fun stores. Would 100% stay again.
The Bootlegger House was a dream come true for a girls getaway. Will was a terrific communicator. The location was perfect. Within walking distance of groceries and many restaurants. Navy Pier and other sites were a short ride share away.
The house was beautiful. The rooftop deck a welcome amenity. The home was very spacious. we enjoyed the many places to gather. There was plenty of room for all of us.
The neighborhood felt safe as we walked to Wrigley Field and restaurants. It was nice to have on-site parking for three cars. We had plenty of space for our family of ten. The kitchen was well stocked and the owner provided extra basic necessities. We would stay here again.
We had a wonderful time visiting Chicago! This property is located in a great neighborhood with lots of places within walking distance. We had plenty of room to spread out and be comfortable. Navy Pier and the River Walk were all a short drive away!
Charming, big house with all of the amenities. Garage, parking pad, rooftop deck, game room, TVs in all rooms. Really well managed and directions easy. Awesome location in Lake View East with easy walk to coffee shops, restaurants. 20 minute walk to Wrigley Field. Hope to stay again!
I highly recommend this property, itâs great for a large group with plenty of space to spread out. Fully equipped kitchen and lots of amenities and character . The location felt safe and quiet and a private garage and outside private area are rare in Chicago!
Back to Chicago with a group for a work trip and of course we went back to the place we stayed at last time. Once you find a gem like this one, you stay with it! They keep this place with all the amenities youâd have at home. Itâs incredibly spacious and the parking spots make it deal for a group. Weâll be back!! Jon