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Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

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January 2025
February 2025

Photo gallery for Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Fridge, microwave, oven, stovetop
6 bedrooms, iron/ironing board, travel crib, free WiFi
Interior
Exterior
Outdoor dining

Reviews

10 out of 10
Exceptional

Entire home

6 bedrooms2 bathrooms

Popular amenities

  • Washer
  • Pet-friendly
  • Barbecue grill
  • Parking available
  • Outdoor space
  • Air conditioning

Explore the area

Map
Chicago, IL
  • Lincoln Park
    ‪5 min walk‬
  • Briar Street Theatre
    ‪8 min walk‬
  • Vic Theatre
    ‪14 min walk‬
  • Chicago, IL (MDW-Midway Intl.)
    ‪35 min drive‬

Room options

About the area

Chicago

City center stay.Within a 10-minute walk of this Lakeview vacation home, you'll find Lincoln Park and Briar Street Theatre. Wrigley Field and Advocate Illinois Masonic Medical Center are also within 2 miles (3 km).
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What's nearby

  • Briar Street Theatre - 8 min walk
  • Wrigley Field - 2 min drive
  • Lincoln Park Zoo - 3 min drive
  • DePaul University-Lincoln Park - 3 min drive
  • Michigan Avenue - 4 min drive

Getting around

  • Chicago Clybourn Station - 5 min drive
  • Belmont Station (Red Line) - 13 min walk
  • Chicago Midway Airport (MDW) - 35 min drive

Restaurants

  • ‪Starbucks - ‬6 min walk
  • ‪Dryhop Brewers - ‬3 min walk
  • ‪Sushi + Rotary Sushi Bar - ‬5 min walk
  • ‪The Coffee & Tea Exchange - ‬7 min walk
  • ‪Stan's Donuts & Coffee - ‬7 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

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.

Property manager

Will Goldstein

Property amenities

Beach

  • Near the beach

Internet

  • Free WiFi

Parking and transportation

  • Electric car charging station on site
  • Onsite parking options include a garage
  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Kitchen island
  • Ice maker
  • Electric kettle
  • Coffee grinder

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bed sheets provided

Bathrooms

  • 2 bathrooms
  • Bathtub or shower
  • Towels provided
  • Shampoo
  • Toilet paper
  • Hair dryer
  • Soap

Living spaces

  • Fireplace
  • Living room
  • Dining room

Entertainment

  • Smart TV
  • Foosball table
  • Arcade/game room
  • Games
  • Books

Outdoor areas

  • Balcony
  • Fenced yard
  • Barbecue grill
  • Garden
  • Outdoor furniture

Laundry

  • Washing machine and dryer

Work spaces

  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Limited housekeeping
  • Iron/ironing board

Location highlights

  • On the lake
  • On the waterfront
  • Next to a golf course
  • In the city center

Safety features

  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)

Policies

Check-in

Check-in time starts at 3:00 PM

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Maximum 2 (weight limit: 50 lbs per pet)
  • Service animals are exempt from fees
  • Note from host: walk your pet off the property to eliminate waste

Children and extra beds

  • Children are welcome.
  • Note from host: We have a baby crib, bed rail and stroller

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.

Property Registration Number R24000123644

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 36 out of 36 reviews" "
Rating 8 - Good. 0 out of 36 reviews" "
Rating 6 - Okay. 0 out of 36 reviews" "
Rating 4 - Poor. 0 out of 36 reviews" "
Rating 2 - Terrible. 0 out of 36 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Michelle R.

Liked: Cleanliness
Classy and Convenient!!
First of all, this property was sooooo easy to travel to. I dont mind city driving, but I do get nervous driving downtown. It was so SIMPLE, literally fool proof!! Conveniently located a few blocks from 41 made for a stress-free 15 minute drive to Shedd Aquarium.The house is absolutely beautiful and in a great neighborhood. The property was very secure, neighbors were friendly, and tons of great places within walking distance. Gorgeous original architecture, built ins and stained glass. The interior is well furnished and nicely decorated. Beds and bedding were very comfortable. The house was filled with entertainment - several tv's, games, foosball, etc. It was too cold to enjoy the deck, but it looked like it could be a lot of fun in the warmer months. We have family in Chicagoland and surrounding areas and we will definitely be booking with Will again!!!
Stayed 2 nights in Jan 2025

10/10 Excellent

Daniel E.

Liked: Cleanliness
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.
Stayed 2 nights in Jan 2025

10/10 Excellent

Lisa W.

Liked: Cleanliness
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.
Stayed 2 nights in Jan 2025

10/10 Excellent

Maureen C., Bettendorf, Iowa

Liked: Cleanliness
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.
Stayed 2 nights in Dec 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness
CLEAN PLACE WITH CHARACTER
We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive.
Stayed 3 nights in Oct 2024

10/10 Excellent

abhinav d.

Liked: Cleanliness
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
Stayed 2 nights in Oct 2024

10/10 Excellent

Felicity S.

Liked: Cleanliness
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.
Stayed 2 nights in Oct 2024

10/10 Excellent

Luke W.

Liked: Cleanliness
Fantastic stay at the bootlegger
Flew into town with a large group for a bachelor party. Walked up to Wrigley for an afternoon game, easily took the train downtown and to/from ORD, had a lot of fun at the myriad bars and restaurants in the area. The host was very accommodating and gracious, I couldn't recommend this place any higher.
Stayed 3 nights in Sep 2024

10/10 Excellent

Jon H.

Liked: Cleanliness
Another great trip to the Chicago Lake Shore
Back to Chicago with a group for a work trip and of course we went back to the place we stayed at last time. Once you find a gem like this one, you stay with it! They keep this place with all the amenities you’d have at home. It’s incredibly spacious and the parking spots make it deal for a group. We’ll be back!! Jon
Stayed 4 nights in Sep 2024

10/10 Excellent

Steven B.

Liked: Cleanliness
DNC Convention
We are a broadcasting team for the Democratic Convention. We could not have had a better place to stay after our long work days. The location for restaurants was fantastic. The size and style of the house was on point. A good stay for the crew.
Stayed 6 nights in Aug 2024

10/10 Excellent

Jeremy S.

Liked: Cleanliness
Great stay!
We loved the location and the place was awesome! It was walking distance to Wrigley Field and the Zoo! Will was good with communication and responsive whenever we reached out. We encountered an issue with one of the toilets, and Will ordered the part for it immediately but it didn't arrive until after we left. It was an inconvenience to work around, but there wasn't much more he could do. Otherwise, we loved our time there and would definitely recommend it to others!
Stayed 5 nights in Jun 2024

10/10 Excellent

Barb L.

Liked: Cleanliness
Nice Oroperty
Comfortable, spacious, good location.
Stayed 2 nights in Jun 2024

10/10 Excellent

Katie G.

Liked: Cleanliness
Great stay, lots of space
Wonderful location, plenty of room, thoroughly enjoyed our stay! We were a group of 30-somethings in town for a weekend. Really enjoyed how close we were to the lake and to coffee shops, restaurants, and transit, but still on a quiet street. It was super convenient, really easy check in with door codes. We enjoyed the roof deck on one nice day, and overall had a great time. Lots of space for all of us! We would happily stay here again.
Stayed 2 nights in Apr 2024

10/10 Excellent

Julita M.

Liked: Cleanliness
Wonderful place for large families - highly recommend
This house is perfect for large families. There is everything you need for cooking, sleeping, and just hanging out. The outdoor patio was a favorite with us all. It almost felt like being at home. We loved the large kitchen table and all of the games in the house. There was so much to do from ages 78 - 24 and so close to everything. We loved there we could park 3 cars safely and did not have to worry about parking garages, or on street. The location was great and I would highly recommend this house to anyone. I know we will be back someday.
Stayed 2 nights in Apr 2024

10/10 Excellent

Peter V., Reno, USA

Liked: Cleanliness
Great house and location!
Charming, big house with all of the amenities. Garage, parking pad, rooftop deck, game room, TVs in all rooms. Really well managed and directions easy. Awesome location in Lake View East with easy walk to coffee shops, restaurants. 20 minute walk to Wrigley Field. Hope to stay again!
Stayed 2 nights in Apr 2024

10/10 Excellent

Francisco R.

Liked: Cleanliness
Great for a Family Getaway
Great property in a good location, Plenty of space to wind down after a day of exploring the city, very comfortable and roomy. Great host.
Stayed 4 nights in Jan 2024

10/10 Excellent

Michelle G.

Liked: Cleanliness
Better Than the Pictures
I grew up in Chicago and most of my family is there so when my Mom passed, of course we were going to Chicago where most of my family still lives. I wanted a place where the out of town people could come together. This was it...beds are comfy, kitchen has what you need. Exit is easy (garbage in bin and sheets by washer). Amazing dining room table for card games (how we roll). And history...which my Mom as lifelong Chicagoan would have lived. Two car garage + parking pad awesome. Unconditionally recommend. Michelle
Stayed 3 nights in Oct 2023

10/10 Excellent

ryan f.

Liked: Cleanliness
nice neighborhood
very nice home well kept up with. 2 min walk to bus and 15 min to train. plenty of space for a family of 6 . thanks will
Stayed 4 nights in Oct 2023

10/10 Excellent

Jennifer V., Dacula, US

Liked: Cleanliness
Fabulous friends trip!
We had a wonderful time visiting Chicago! This property is located in a great neighborhood with lots of places within walking distance. We had plenty of room to spread out and be comfortable. Navy Pier and the River Walk were all a short drive away!
Stayed 2 nights in Oct 2023

10/10 Excellent

Jon H.

Liked: Cleanliness
What a place!
This place is a gem! Located a couple of blocks from the lake, you’ve got great access to the biking and running paths along the water. A few blocks to the west and you’ve got restaurants, shopping, etc.. it was awesome! The place itself is so well equipped with everything you could need. The bedroom count is great so the group could have their own bedrooms but what tops that is the amount of common space for hanging out. Can’t say how much we loved the place! We’ll be back…
Stayed 3 nights in Sep 2023

10/10 Excellent

Edwin F T.

Liked: Cleanliness
The Best Private Accommadations We Ever Stayed At
Starting with the owner who was one of the best I have ever worked with, he promptly return all my calls, knew the area, was always accommodating, and was a professional at all times. The house was awesom, fully equipped with the best of appliances, had a large amount of kitchen ware, a large amount of bathroom supplies,bed linens and towels were plentiful, and there were many board games to playl The house was spotless. The decor was beautiful. Excellent location. Everyone in our party said they would highly recommend this property to stay at.
Stayed 4 nights in Aug 2023

10/10 Excellent

Yan C.

Liked: Cleanliness
Wills is great
The property manager Wills is very responsive. You will like this house. Yan
Stayed 4 nights in Jul 2023

10/10 Excellent

Trisha N.

Liked: Cleanliness
Chicago Gem
This kind host and well-appointed home-away-from-home helped us have a top 10 family reunion vacation.We accessed Chicago's best from here. Our group of 13 needed space to make meals and eat together, play gamesand have separate bedrooms. We couldn't believe our luck when we found this home within walking distance of Lake Michigan, transit and local restaurants. We were delighted by the amount of space, the smart functional layouts of each room, the quality of the furnishings and (for me) the décor and history of the home. It is hard to please 13 people, but we were ALL pleased. In the kitchen, we had all the tools we needed for cooking and serving, and they were good quality. Teflon pans in great condition, good knives, full sets of dishes and glasses, large refrigerator, gas range. The dining table had cloth covered chairs and generous seating. The huge living connected to a charming sunroom featuring two high-top tables, allowing everyone to find favorite spots for eating, conversation or games. The bedding was high quality with comfy sheets and pillows. The laundry room provided space for families to keep up with their wash in newer appliances that worked great. The rooftop provided another great gathering space. It's where we had morning yoga! On the 4th of July, we avoided the crowds and had our own rooftop BBQ. Home and garden decorating details such floral arrangements and giant hostas were icing on the cake for me. Will, our host was incredibly responsive throughout.
Stayed 7 nights in Jul 2023

10/10 Excellent

Tammy V.

Liked: Cleanliness
Great Stay
The neighborhood felt safe as we walked to Wrigley Field and restaurants. It was nice to have on-site parking for three cars. We had plenty of space for our family of ten. The kitchen was well stocked and the owner provided extra basic necessities. We would stay here again.
Stayed 5 nights in Jun 2023

10/10 Excellent

Nicole S.

Liked: Cleanliness
Wonderful property
I highly recommend this property, it’s great for a large group with plenty of space to spread out. Fully equipped kitchen and lots of amenities and character . The location felt safe and quiet and a private garage and outside private area are rare in Chicago!
Stayed 3 nights in Jun 2023