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Entire home

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Lakefront holiday home with kitchen and balcony

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

Fridge, microwave, oven, stovetop
Fridge, microwave, oven, stovetop
Exterior
Interior
Outdoor dining
East Lakeview's historic single-family home, built by a bootlegger in the 1920s, now welcomes you to its unique space. With plenty of room for up to 22 guests, enjoy activities like foosball or explore the nearby Wrigley and Lincoln Park areas.

Reviews

10 out of 10
Exceptional

Entire home

6 bedrooms2 bathrooms

Popular amenities

  • Dryer
  • Washer
  • Pet-friendly
  • Fireplace

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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 amenities

Beach

  • Beach nearby

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Electric car charging station on site
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Up to 23 kg per pet

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Housekeeping (limited availability)
  • Iron/ironing board

Location highlights

  • In the city centre
  • Next to a golf course
  • On a lake
  • On the waterfront

Things to do

  • Arcade/game room
  • Foosball table

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Electric car charging station
  • Garden

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Inspiring Stone Grotto Sleeps 10-20 & Free Parking

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  • Washer
  • Dryer
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Policies

Check-in

Check-in time starts at 3:00 PM

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
2 total (up to 23 kg per pet)
Note from host: walk your pet off the property to eliminate waste

Children and extra beds

Children are welcome
Note from host: We have a baby crib, bed rail and stroller

Events

No events allowed

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number R24000123644

About the area

Map
Chicago, IL

What's nearby

  • 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
  • Michigan Avenue - 5 min drive - 5.6 km
  • Navy Pier - 10 min drive - 8.4 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
  • ‪Wilde Bar & Restaurant - ‬3 min walk
  • ‪The Bagel - ‬4 min walk
  • ‪Fancy Plants Cafe - ‬3 min walk
  • ‪Wake ‘n Bacon - ‬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.

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

10

Cleanliness

9.8

Location
Rating 10 - Excellent. 44 out of 46 reviews
Rating 8 - Good. 2 out of 46 reviews
Rating 6 - Okay. 0 out of 46 reviews
Rating 4 - Poor. 0 out of 46 reviews
Rating 2 - Terrible. 0 out of 46 reviews

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

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

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

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

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

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

Edwin F T.

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

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

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

Steph L.

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

Spacious living

Spacious, charming, very comfortable, very clean, good location, near the lake. Main floor has two bedrooms, kitchen, living room, dining room with nice large table, breakfast nook, and bathroom. Downstairs has four bedrooms, family room, foosball table, bathroom, and washer & dryer. Both upstairs and downstairs are well stocked with board games. Plenty of room for a large group to comfortably sleep, cook, eat, and hang out together.
Stayed 3 nights in Jan 2023

10/10 Excellent

Jeremy S.

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

Great stay!

We loved the location and the place was awesome! It was walking distance to Wrigley Field and the Zoo! Will was good with communication and responsive whenever we reached out. We encountered an issue with one of the toilets, and Will ordered the part for it immediately but it didn't arrive until after we left. It was an inconvenience to work around, but there wasn't much more he could do. Otherwise, we loved our time there and would definitely recommend it to others!
Stayed 5 nights in Jun 2024

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

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

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

Leng Y.

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

Fun time

Good time
Stayed 2 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

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

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

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

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

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

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

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