Entire home
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
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Reviews
10 out of 10
Exceptional
6 bedrooms 2 bathrooms Sleeps 20
Popular amenities
Explore the area
Chicago, IL
- Wrigley Field19 min walk
- Lincoln Park Zoo2 min drive
- Michigan Avenue5 min drive
- Chicago, IL (MDW-Midway Intl.)22 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.
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.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
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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 23 kg per pet (limit 2 pets total)
Walk your pet off the property to eliminate waste
Smoking
Smoking is not permitted
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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property Registration Number R24000123644
About the area
Chicago
Located in Lakeview, a neighbourhood in Chicago, this holiday home is next to a golf course and on the waterfront. Merchandise Mart and Willis Tower are notable landmarks, and travellers looking to shop may want to visit Michigan Avenue and Navy Pier. Travelling with kids? Make time for Field Museum of Natural History, or head to an event or a match at Wrigley Field.
Chicago, IL
What's nearby
- Wrigley Field - 19 min walk - 1.7 km
- DePaul University-Lincoln Park - 2 min drive - 2.1 km
- Lincoln Park Zoo - 2 min drive - 2.5 km
- Michigan Avenue - 5 min drive - 5.3 km
- Navy Pier - 9 min drive - 8.1 km
Getting around
Restaurants
- DryHop Brewers - 3 min walk
- Wilde Bar & Restaurant - 3 min walk
- The Bagel - 4 min walk
- Fancy Plants Cafe - 3 min walk
- Chicken Hut - 4 min walk
Frequently asked questions
About the host
Hosted by Will Goldstein

Premier Host
They consistently provide great experiences for their guests
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