Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
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1 night
1 room, 2 adults, 0 children
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Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

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Chicago, Illinois 60657, United States
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hotel overview picture
Highlights
Ideal location
Top local pick
Lots to do
Sparkling clean
Excellent service
Amenities
Wi-Fi in Public Areas
Table Football
Game Room
Barbecue
No Smoking in Public Areas
Garden
Children's Desktop Game/ Jigsaw Puzzle
Children's Toys
All amenities
Property Description
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.About pets:Pets allowed: less than 50 lbs per pet (limit 2 pets total).Walk your pet off the property to eliminate waste.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.We have a baby crib, bed rail and stroller.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.
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10.0/10
Outstanding
Cleanliness10.0
Amenities10.0
Location10.0
Service10.0
All 39 reviews
Surroundings
Metro: Belmont
(1.0 km)
Metro: Wellington
(1.3 km)
Airport: O'Hare International Airport
(24.5 km)
Airport: Midway International Airport
(26.2 km)
Train: Millennium Station
(8.1 km)
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Overview

Rooms

Guest Reviews

Services & Amenities

Policies

Host

6 Bedrooms Private Vacation Home
15

6 Bedrooms Private Vacation Home

6 bedrooms: 7 queen beds and 1 king bed
Free Wi-Fi
Non-smoking
Air Conditioning
Refrigerator
TV
In-room Wi-Fi
Room Details
Check Availability

Guest Reviews

10.0/10
Outstanding
39 reviews
Verified Reviews
  • Cleanliness10.0
  • Amenities10.0
  • Location10.0
  • Service10.0
Average for similar properties in Chicago
Most Mentioned
T‍o‍n‍y‍ ‍P‍.
February 23, 2025
Great places! This is one of the best rentals I've stayed at. Clean, well located and priced well. Would definitely recommend.
D‍a‍n‍i‍e‍l‍ ‍E‍.
January 6, 2025
Perfect for a bachelor party 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.
C‍a‍r‍l‍ ‍W‍.
January 27, 2025
Chicago weekend Houseowner was very accommodating. Everything was just as it appeared online. Definitely would stay there if ever in chicago again
L‍i‍s‍a‍ ‍W‍.
January 4, 2025
Amazing Place 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.
P‍a‍u‍l‍ ‍M‍.
February 4, 2025
Amazing location ; amazing house 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 !
S‍u‍s‍a‍n‍ ‍P‍.
January 27, 2025
Great place! Very comfortable and welcoming. a great stay for a large family. We enjoyed everything about our stay. Will be back!
M‍a‍u‍r‍e‍e‍n‍ ‍C‍.
December 28, 2024
Great find. It is rare to find a place in Chicago with room for so many to stay under one roof and which includes the bonus of garage parking. The neighborhood was safe and we found additional free street parking with no trouble. It was within walking distance to public transportation so we were able to take a bus to Lincoln Park Zoo to enjoy Zoo Lights. We also enjoyed a short walk to a local park. It was nice to have a sitting room upstairs to gather and another space downstairs. There was a high chair that came in handy and the large kitchen table was perfect.
F‍e‍l‍i‍c‍i‍t‍y‍ ‍S‍.
October 5, 2024
Beauty and convenience 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.
a‍b‍h‍i‍n‍a‍v‍ ‍d‍.
October 10, 2024
Great Place and awesome neighborhood Dear Will, I wanted to take a moment to thank you for hosting us at your lovely property. We truly enjoyed our stay—your 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

Services & Amenities

More Amenities
Internet
Activities
Public Areas
Facilities for Children

Property Policies

Check-in and Check-out Times
Check-in: After 15:00
Check-out: Before 11:00
Child Policies
Children of all ages are welcome at this property.
Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.

Cots and Extra Beds
Please contact the hotel for details about cot and extra bed policies.

Property host

Will Goldstein

About this property

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.About pets:Pets allowed: less than 50 lbs per pet (limit 2 pets total).Walk your pet off the property to eliminate waste.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.We have a baby crib, bed rail and stroller.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.
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Frequently Asked Questions

What are some things to do near Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

You can visit the following landmarks near Chicago Bootlegger House Sleeps 11-22 with 3 parking spots: Merlo Branch, Chicago Public Library, 390m from your search (straight-line distance).

What are the check-in and check-out times at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

The check-in time at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots is 15:00 and the check-out time is 11:00.

Which airport is closest to Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

O'Hare International Airport is the closest airport to Chicago Bootlegger House Sleeps 11-22 with 3 parking spots, and it is about 34 mins from hotel by car (24.5 km).

How much does it cost to stay at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

Prices at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots are subject to change according to dates, hotel policy, and other factors. To view prices, please search for the dates you wish to stay at the hotel.

About This Property

Nearest AirportO'Hare International Airport
Distance to Airport25.21KM
Nearest Train StationMillennium Station
Distance to Train Station8.05KM
Nearest Metro StationBelmont
Distance to Metro Station1.07KM
Hotel Star Rating4