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Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

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

A cozy living room with a fireplace, leather sofas, and a dining area with a green wall and large windows.
An outdoor patio with metal tables and chairs, a grill, and a decorative fence.
A two-story building with a beige facade, black-framed windows, and a black metal fence in front.
A dining area with a wooden table and patterned chairs, a chandelier, and a plant shelf.
A kitchen with wooden cabinets, a microwave, a stove, and a sink.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Wrigley Field
6 bedrooms2 bathroomsSleeps 20

Popular amenities

  • Garage parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Chicago, IL
  • Place, Lincoln Park
    ‪3 min walk‬
  • Place, Vic Theatre
    ‪13 min walk‬
  • Place, Wrigley Field
    ‪19 min walk‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪33 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
Number of living rooms
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.
Our prices include all fees. No hidden fees.

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House Rules

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

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

No events allowed
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Pets

Pets allowed: less than 23 kg per pet (limit 2 pets total)
Walk your pet off the property to eliminate waste
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number R24000123644
Property # 2779421vb
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
Safety features at this property include a fire extinguisher
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

About the area

Chicago

Located in Lakeview, a neighbourhood in Chicago, this holiday home is next to a golf course and on the waterfront. Chicago Theatre and Art Institute of Chicago 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 Griffin Museum of Science and Industry, or head to an event or a match at Wrigley Field.
View more Holiday homes in ChicagoOpens in a new window
Map
Chicago, IL

What's nearby

  • Lincoln Park - 3 min walk - 0.3 km
  • Vic Theatre - 13 min walk - 1.1 km
  • Wrigley Field - 19 min walk - 1.7 km
  • Theater Wit - 2 min drive - 1.5 km
  • Lincoln Park Zoo - 4 min drive - 2.5 km

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
  • ‪Owen’s Famous Coffee & Provisions - ‬6 min walk
  • ‪Le Petit Marcel - ‬7 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 23 kg per pet.

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

As of 21 Aug 2026, prices found for a 1-night stay for 2 adults at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots on 17 Nov 2026 start from £998, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

On-site parking is available at the property.

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.

About the host

Hosted by Will Goldstein

Host profile image

Premier Host

They consistently provide great experiences for their guests
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