Entire home

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.
A dining area with a wooden table and patterned chairs, a chandelier, and a plant shelf.
A two-story building with a beige facade, black-framed windows, and a black metal fence in front.
An outdoor patio with metal tables and chairs, a grill, and a decorative fence.
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

  • Balcony
  • Arcade/game room
  • Barbecue
  • Electric vehicle charging point
  • Pet-friendly
  • Air-conditioning

Explore the area

View 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

Where you'll sleep

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.

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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
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. Merchandise Mart and Cloud Gate are notable landmarks, and travellers looking to shop may want to visit Michigan Avenue and Navy Pier. Travelling with kids? Make time for Lincoln Park Zoo, or head to an event or a match at Wrigley Field.
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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

  • ‪The Coffee & Tea Exchange - ‬7 min walk
  • ‪DryHop Brewers - ‬3 min walk
  • ‪Sushi+ Rotary Sushi Bar - ‬5 min walk
  • ‪Wilde Bar & Restaurant - ‬3 min walk
  • ‪Owen’s Famous Coffee & Provisions - ‬6 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 15 September 2026, prices found for a 1-night stay for 2 adults at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots on 13 December 2026 start from NZ$2,330, 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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