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Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

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Interior
Living area
Interior
Interior
Living area

Reviews

10 out of 10
Exceptional
6 bedrooms2 bathroomsSleeps 20

Popular amenities

  • Dryer
  • Washer
  • Fireplace
  • Pet-friendly
  • Barbecue grill

Explore the area

Map
Chicago, IL
  • Lincoln Park
    ‪5 min walk‬
  • Wrigley Field
    ‪2 min drive‬
  • Lincoln Park Zoo
    ‪3 min drive‬
  • Chicago, 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

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

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  • Washer
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10.0 out of 10, (126 reviews)
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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

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
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 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.
Map
Chicago, IL

What's nearby

  • Lincoln Park - 5 min walk - 0.5 km
  • Wrigley Field - 2 min drive - 1.8 km
  • Lincoln Park Zoo - 3 min drive - 2.8 km
  • DePaul University-Lincoln Park - 3 min drive - 2.8 km
  • Michigan Avenue - 4 min drive - 5.1 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
  • ‪The Coffee & Tea Exchange - ‬7 min walk
  • ‪Stan's Donuts & Coffee - ‬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.

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.
Learn moreOpens in a new window
Rating 10 - Excellent. 41 out of 41 reviews
Rating 8 - Good. 0 out of 41 reviews
Rating 6 - Okay. 0 out of 41 reviews
Rating 4 - Poor. 0 out of 41 reviews
Rating 2 - Terrible. 0 out of 41 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Tony P.

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

Great places!

This is one of the best rentals I've stayed at. Clean, well located and priced well. Would definitely recommend.
Stayed 4 nights in Feb 2025

10/10 Excellent

Susan P.

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

Great place!

Very comfortable and welcoming. a great stay for a large family. We enjoyed everything about our stay. Will be back!
Stayed 2 nights in Jan 2025

10/10 Excellent

Leng Y.

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

Fun time

Good time
Stayed 2 nights in Feb 2025

10/10 Excellent

Carl W.

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

Chicago weekend

Houseowner was very accommodating. Everything was just as it appeared online. Definitely would stay there if ever in chicago again
Stayed 3 nights in Jan 2025

10/10 Excellent

Lisa W.

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

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

Paul M.

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

Amazing location ; amazing house

We stayed here in January to visit some family and enjoy the city. The location of this place is amazing. its right downtown , very walkable to everything. The parking is great, with the 2 car garage it was heaven for being in the city. The property is so nice. Its massive. upstairs and downstairs ; with room for so many people. We ended up only have four people ; and just loved it. The living room is so cozy, with the fireplace and sofas, the property was perfect. Matches all the pictures. And the host communication was perfect. Highly recommend !
Stayed 5 nights in Jan 2025

10/10 Excellent

Daniel E.

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

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

Barb L.

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

Nice Oroperty

Comfortable, spacious, good location.
Stayed 2 nights in Jun 2024

10/10 Excellent

Maureen C.

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

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, check-in, communication, location, listing accuracy

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

Luke W.

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

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

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

Steven B.

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

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

abhinav d.

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

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, check-in, communication, location, listing accuracy

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

Michelle R.

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

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

Jon H.

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

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

Katie G.

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

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

Stefani Z.

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

Great Family Stay!

This place was wonderful! It was so clean, had plenty of space for our group and had everything that we needed. Location was perfect! Even though we had a rental car, there was so much within walking distance. So many great restaurants. Having that garage to park in was the cherry on top!
Stayed 4 nights in May 2023

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

Jay C.

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

Cubs Weekend

Amazing place to stay for a guys weekend at Wrigley! Plenty of space, multiple bedrooms equipped for a large group, great living room set-up for hanging/gathering. Neighborhood is wonderful and easy to walk to several close restaurants and bars. I would definitely stay here again.
Stayed 2 nights in Apr 2023

10/10 Excellent

Sarah B.

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

Great place for sleeping a crowd

This was an amazing house! Seemingly infinite beds and bedrooms, but still with spacious common areas. The neighborhood is wonderful--easy walk to the lake with lots of restaurants and fun stores. Would 100% stay again.
Stayed 2 nights in May 2023

10/10 Excellent

Jennifer V., Dacula, US

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

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

Tammy V.

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

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, check-in, communication, location, listing accuracy

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

About the host

Hosted by Will Goldstein

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Premier Host

They consistently provide great experiences for their guests
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