Entire home

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

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

Living area
Living area
Interior
Interior
Interior

Overview of Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Reviews
10 out of 10 Exceptional
6 bedrooms2 bathroomsSleeps 20

Popular amenities

  • Hot tubHot tubHot tub
  • FireplaceFireplaceFireplace
  • Pet-friendlyPet-friendlyPet-friendly
  • Free WiFiFree WiFiFree WiFi
  • Air conditioningAir conditioningAir conditioning
  • WasherWasherWasher

Explore the area

Map
Chicago, IL
  • Popular LocationWrigley Field2 min drive
  • Popular LocationLincoln Park Zoo3 min drive
  • Popular LocationChicago Riverwalk6 min drive
  • AirportChicago, IL (MDW-Midway Intl.)35 min drive

Rooms & beds

6 bedrooms (sleeps 20)

Bedroom 1

2 Queen Beds

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Bedroom 5

2 Queen Beds

Bedroom 6

1 King Bed

Common area 1

1 Double Futon

Living Room 3

2 Single Futons

2 bathrooms

Bathroom 1

Bathtub or shower · Bathtub · Toilet · Shower only

Bathroom 2

Bathtub or shower · Bathtub · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Outdoor play area
Garden
Dining Area

About this property

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
Premier Host
Premier Host

Amenities

Hot tub
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

House Rules

Check in after 3:00 PM
Check out before 11:00 AM

Children

Children allowed: ages 0–17
We have a baby crib, bed rail and stroller

Events

No events allowed

Pets

Pets allowed: less than 50 lb per pet (limit 2 pets total)
Walk your pet off the property to eliminate waste

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
Property Registration Number R22000081519

About the area

Chicago

This holiday home is located in Lakeview, a neighbourhood in Chicago, and is next to a golf course and on the waterfront. Art Institute of Chicago and Chicago Theatre are cultural highlights, and some of the area's popular attractions include Lincoln Park Zoo and Field Museum of Natural History. Travelling with kids? Make time for Chicago Museum of Science and Industry, or head to an event or a match at Wrigley Field.
Map
Chicago, IL

What's nearby

  • Wrigley Field - 2 min drive
  • Lincoln Park Zoo - 3 min drive
  • Michigan Avenue - 4 min drive
  • Chicago Riverwalk - 6 min drive
  • Navy Pier - 7 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
  • Wake ‘n Bacon - 4 min walk
  • The Bagel Restaurant & Deli - 4 min walk
  • Wilde Bar & Restaurant - 3 min walk

Frequently asked questions

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

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 50 lb per pet.

What time is check-in at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

Check-in begins at 3:00 PM.

What time is check-out at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

Checkout is at 11:00 AM.

Where is Chicago Bootlegger House Sleeps 11-22 with 3 parking spots located?

This family-friendly Chicago holiday home is located on the waterfront, within 1 mi (2 km) of Lincoln Park and Wrigley Field. Lake Michigan is 1.8 mi (2.9 km) away. Belmont Station (Red Line) is 13 minutes by foot and Wellington Station is 15 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 23 out of 23 reviews" "
Rating 8 - Good. 0 out of 23 reviews" "
Rating 6 - Okay. 0 out of 23 reviews" "
Rating 4 - Poor. 0 out of 23 reviews" "
Rating 2 - Terrible. 0 out of 23 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Julita M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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, check-in, communication, location, listing accuracy
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, check-in, communication, location, listing accuracy
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, check-in, communication, location, listing accuracy
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

About the host

Hosted by Will Goldstein

Host profile image

Premier Host

Premier Host
They consistently provide great experiences for their guests
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