House in Chicago, IL
20 guests · 6 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
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.
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.
Amenities at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Non-smoking
Pets allowed
Map of Chicago, IL
Ratings and reviews
10.0 / 10.0Outstanding·Dec 2025
Great house, really enjoyed our stay here! Very comfy, plenty of room, had character and we liked it more than the pictures, and very convenient to get downtown or to Wrigley from. Bus and metro stops are right nearby, and also a short trip on ride-share apps. It's an older house so a bit squeakier in the basement than upstairs, but that's to be expected and I'd happily stay here again on future visits! I really liked the character, style, and location of the house - was very comfortable and we really enjoyed staying here!
10.0 / 10.0Outstanding·Sep 2025
A unique property in a very safe, friendly neighborhood. The house was lovely, clean, in excellent repair with lots of room, beds, chairs, TVs, dining area, rooftop patio and everything you could possibly need. Walkable neighborhood with many places to eat and get groceries. Walked and took the bus. Garage was plenty big. Park your car and get out and see the city.
10.0 / 10.0Outstanding·Sep 2025
Just stayed here for the 3rd time! The owner/manager continues to keep the place in great shape and even seems to have added small “niceties” to the property. Many places you stay at over time, start to get “let-go” but this one just gets better. We’ll be looking to book again as soon as our next dates are set!!
8.0 / 10.0Excellent·Jul 2025
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.
$$$$
Top rated by guests
10.0Outstanding
(48 Ratings)
"Great house, really enjoyed our stay here! Very comfy, plenty of room, had character and we liked it more than the pictures, and very convenient to get downtown or to Wrigley from. Bus and metro stops..."
Mark J.Don't miss out! Price and availability may change
