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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, Loved by Guests
Top 10% based on
6 bedrooms2 bathroomsSleeps 20

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning

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 (MDW-Midway Intl.)
    ‪24 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.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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Interior
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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
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. Chicago Theatre and Art Institute of Chicago are cultural highlights, and some of the area's popular attractions include Field Museum of Natural History and Griffin Museum of Science and Industry. Looking to enjoy an event or a game? See what's going on at Wrigley Field or United Center.
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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
  • DePaul University-Lincoln Park - 2 min drive - 2.1 km
  • Lincoln Park Zoo - 3 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

  • ‪DryHop Brewers - ‬3 min walk
  • ‪Taco Bell - ‬6 min walk
  • ‪Sushi+ Rotary Sushi Bar - ‬5 min walk
  • ‪Wilde Bar & Restaurant - ‬3 min walk
  • ‪The Bagel - ‬4 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 5 Mar, 2026, prices found for a 1-night stay for 2 adults at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots on 3 May, 2026 start from S$641, 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.

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. 46 out of 48 reviews
Rating 8 - Good. 2 out of 48 reviews
Rating 6 - Okay. 0 out of 48 reviews
Rating 4 - Poor. 0 out of 48 reviews
Rating 2 - Terrible. 0 out of 48 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Peggy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was immediately responsive, with answers and kindness. Excellent communication.Great place to make memories! My family of six, my sister's family of 5, coming from Chicago, Minneapolis, St. Louis, Indianapolis (area) and Colorado Springs - great place for us all to gather...it was a great location, with lots to see in the neighborhood, as well.House had plenty of space! Plenty of towels, beds, areas to gather, and a well-stocked kitchen.
Stayed 3 nights in Dec 2025

10/10 Excellent

Mark J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house, really enjoyed our stay here! Very comfy, plenty of room, had character and we liked it more than the pictures, and very convenient to get downtown or to Wrigley from. Bus and metro stops are right nearby, and also a short trip on ride-share apps. It's an older house so a bit squeakier in the basement than upstairs, but that's to be expected and I'd happily stay here again on future visits! I really liked the character, style, and location of the house - was very comfortable and we really enjoyed staying here!
Stayed 4 nights in Nov 2025

10/10 Excellent

Jon H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just stayed here for the 3rd time! The owner/manager continues to keep the place in great shape and even seems to have added small “niceties” to the property. Many places you stay at over time, start to get “let-go” but this one just gets better. We’ll be looking to book again as soon as our next dates are set!!
Stayed 3 nights in Sep 2025

8/10 Good

Judy G.

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

Wedding weekend

Good location - plenty of room
Stayed 4 nights in May 2025

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

Jennifer B.

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

90th Birthday Celebration

We had a fabulous time and enjoyed our stay very much. Will was very helpful and went above and beyond to accommodate our needs.
Stayed 4 nights in May 2025

10/10 Excellent

Donald K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A unique property in a very safe, friendly neighborhood. The house was lovely, clean, in excellent repair with lots of room, beds, chairs, TVs, dining area, rooftop patio and everything you could possibly need. Walkable neighborhood with many places to eat and get groceries. Walked and took the bus. Garage was plenty big. Park your car and get out and see the city.
Stayed 3 nights in Sep 2025

8/10 Good

Robert W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Over all a great place to stay if you want to see the city and all the attractions. The house was clean. The Foosball table needs some work missing a couple of screws, lots of board games for the kids but a lot of them were missing pieces and need to be thrown out.
Stayed 4 nights in Jul 2025

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

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

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

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

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

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

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

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

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

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

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

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

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

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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