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 / 10Outstanding·Jul 2026
We were really impressed by this place, looks even nicer than the photos! Lots of space for our group, loved the Spanish vibe and outdoor patio.
10 / 10Outstanding·Jul 2026
Great house in perfect location. Had everything we needed and so much more.
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.
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Top rated by guests
10Outstanding
(55 Ratings)
"We were really impressed by this place, looks even nicer than the photos! Lots of space for our group, loved the Spanish vibe and outdoor patio."
Madeline G.Don't miss out! Price and availability may change
