Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Top rated by guests
Interior
Private kitchen
Private kitchen
Private kitchen
Private kitchen
review stars
10Outstanding
(53 Ratings)
"Family friendly for group of adults. Great garage rooftop patio to sit and enjoy time together. House has multiple large gathering areas (large dining room table, family room w/ adjacent front room-..."
Verified guest
Don't miss out! Price and availability may change
10 / 10
Outstanding(53 Ratings)

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.

Amenities at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Non-smoking
Pets allowed

Map of Chicago, IL


Ratings and reviews

10 / 10
Outstanding(53 Ratings)
10 / 10Outstanding·May 2026
Family friendly for group of adults. Great garage rooftop patio to sit and enjoy time together. House has multiple large gathering areas (large dining room table, family room w/ adjacent front room-this has 2 high tops that seat 8, and large basement family room with adjacent game areas, besides the patio). Kitchen is sufficient to facilitate meals, and having a dual 12 cup coffee maker assures you won' run out of coffee quickly in the am for a large group. Location is such that it is located at the end of the block in a relatively quiet neighborhood that you can access the city hustle and bustle by walking a block or 2, but you're buffered from most of the noise. Our group walked to Wrigley Field about a mile plus to the northwest but were able to also walk south to north Lincoln Park too. Like the neighborhood, this home is older, historic with lots of character. Our group had a very nice stay here.
10 / 10Outstanding·Dec 2025
Host was immediately responsive, with answers and kindness. Excellent communication.Great place to make memories! My family of six, my sister's family of 5, coming from Chicago, Minneapolis, St. Louis, Indianapolis (area) and Colorado Springs - great place for us all to gather...it was a great location, with lots to see in the neighborhood, as well.House had plenty of space! Plenty of towels, beds, areas to gather, and a well-stocked kitchen.
10 / 10Outstanding·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 / 10Outstanding·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.

$$$$
expedia logo

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Chicago Bootlegger House Sleeps 11-22 with 3 parking spots pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

We found 2 amenities for this rental. This includes non-smoking, and pets allowed.