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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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
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

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
Check Availability
Guest Reviews
10.0/10
Outstanding
39 reviews

- Cleanliness10.0
- Amenities10.0
- Location10.0
- Service10.0
Average for similar properties in Chicago

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
Most Popular Amenities
Wi-Fi in Public Areas
More Amenities
Internet
Wi-Fi in Public Areas
Activities
Table Football
Game Room
Public Areas
Barbecue
No Smoking in Public Areas
Garden
Facilities for Children
Children's Desktop Game/ Jigsaw Puzzle
Children's Toys
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 some things to do near Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?
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.What are the check-in and check-out times at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?
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).Which airport is closest to Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?
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.How much does it cost to stay at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?
About This Property
Nearest Airport | O'Hare International Airport |
---|---|
Distance to Airport | 25.21KM |
Nearest Train Station | Millennium Station |
Distance to Train Station | 8.05KM |
Nearest Metro Station | Belmont |
Distance to Metro Station | 1.07KM |
Hotel Star Rating | 4 |