Entire home·Private host

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. - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)
A two-story building with a beige facade, black-framed windows, and a black metal fence in front. - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)
A dining area with a wooden table and patterned chairs, a chandelier, and a plant shelf. - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)
An outdoor patio with metal tables and chairs, a grill, and a decorative fence. - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)
A kitchen with wooden cabinets, a microwave, a stove, and a sink. - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)
Wrigley Field is located near Chicago Bootlegger House Sleeps 11-22 with 3 parking spots, which provides an adjacent golf course, a garden and a playground. In addition to an arcade/games room and laundry facilities, guests can connect to free in-room WiFi, with a speed of 500+ Mbps (good for 6+ people or 10+ devices).

Reviews

10 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

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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About the area

Located in Lakeview, a neighbourhood in Chicago, this holiday home is next to a golf course and on the waterfront. The area's natural beauty can be seen at Lake Michigan and Millennium Park, while Chicago Theatre and Art Institute of Chicago are cultural highlights. Looking to enjoy an event or a game? See what's going on at Wrigley Field or United Center. Visit our Chicago travel guide
View more Holiday homes in Chicago
Map
Chicago, IL

What's nearby

  • A city skyline with a river, green spaces, and a baseball field.
    Lincoln Park
    3 min walk - 0.3 km
  • An aerial view of a baseball stadium surrounded by urban buildings.
    Wrigley Field
    19 min walk - 1.7 km
  • A sign for the Pritzker Family Children's Zoo surrounded by autumn foliage.
    Lincoln Park Zoo
    4 min drive - 2.5 km
  • Vic Theatre
    13 min walk - 1.1 km
  • Theater Wit
    2 min drive - 1.5 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
  • Sushi+ Rotary Sushi Bar
    5 min walk
  • DryHop Brewers
    3 min walk
  • Wilde Bar & Restaurant
    3 min walk
  • Taco Bell
    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 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.

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Reviews

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots Reviews

10

Exceptional

9.8

Cleanliness

9.8

Location
Rating 10 - Excellent. 53 out of 56 reviews
Rating 8 - Good. 3 out of 56 reviews
Rating 6 - Okay. 0 out of 56 reviews
Rating 4 - Poor. 0 out of 56 reviews
Rating 2 - Terrible. 0 out of 56 reviews

Reviews

Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

8/10 Good

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

Wedding weekend

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

10/10 Excellent

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
Verified review

10/10 Excellent

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

Nice Oroperty

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

10/10 Excellent

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
Verified review

10/10 Excellent

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

Fun time

Good time
Stayed 2 nights in Feb 2025
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

The Best Private Accommadations We Ever Stayed At

Starting with the owner who was one of the best I have ever worked with, he promptly return all my calls, knew the area, was always accommodating, and was a professional at all times. The house was awesom, fully equipped with the best of appliances, had a large amount of kitchen ware, a large amount of bathroom supplies,bed linens and towels were plentiful, and there were many board games to playl The house was spotless. The decor was beautiful. Excellent location. Everyone in our party said they would highly recommend this property to stay at.
Stayed 4 nights in Aug 2023
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

What a place!

This place is a gem! Located a couple of blocks from the lake, you’ve got great access to the biking and running paths along the water. A few blocks to the west and you’ve got restaurants, shopping, etc.. it was awesome! The place itself is so well equipped with everything you could need. The bedroom count is great so the group could have their own bedrooms but what tops that is the amount of common space for hanging out. Can’t say how much we loved the place! We’ll be back…
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

Wonderful place for large families - highly recommend

This house is perfect for large families. There is everything you need for cooking, sleeping, and just hanging out. The outdoor patio was a favorite with us all. It almost felt like being at home. We loved the large kitchen table and all of the games in the house. There was so much to do from ages 78 - 24 and so close to everything. We loved there we could park 3 cars safely and did not have to worry about parking garages, or on street. The location was great and I would highly recommend this house to anyone. I know we will be back someday.
Stayed 2 nights in Apr 2024
Verified review

10/10 Excellent

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

Better Than the Pictures

I grew up in Chicago and most of my family is there so when my Mom passed, of course we were going to Chicago where most of my family still lives. I wanted a place where the out of town people could come together. This was it...beds are comfy, kitchen has what you need. Exit is easy (garbage in bin and sheets by washer). Amazing dining room table for card games (how we roll). And history...which my Mom as lifelong Chicagoan would have lived. Two car garage + parking pad awesome. Unconditionally recommend. Michelle
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We were really impressed by this place, looks even nicer than the photos! Lots of space for our group, loved the Spanish vibe and outdoor patio.
Stayed 2 nights in Jul 2026