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Entire home·Private host

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Gather with friends and family in this spacious retreat near iconic Chicago landmarks. Enjoy games and good times together.

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

Fridge, microwave, oven, stovetop
Outdoor dining
Exterior
6 bedrooms, iron/ironing board, travel cot, free WiFi
Interior

Reviews

10 out of 10
Exceptional

Entire home

6 bedrooms2 bathrooms

Popular amenities

  • Washer
  • Pet-friendly
  • Barbecue grill
  • Parking available
  • Outdoor space
  • Air conditioning

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 manager

Will Goldstein

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

  • 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

Similar properties

Interior

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, 123 reviews
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

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

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 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 - 2 min drive
  • Lincoln Park Zoo - 3 min drive
  • DePaul University-Lincoln Park - 3 min drive
  • Michigan Avenue - 4 min drive
  • Navy Pier - 7 min drive

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.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 39 out of 39 reviews
Rating 8 - Good. 0 out of 39 reviews
Rating 6 - Okay. 0 out of 39 reviews
Rating 4 - Poor. 0 out of 39 reviews
Rating 2 - Terrible. 0 out of 39 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Francisco R.

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

Katie G.

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

Peter V.

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

Stefani Z.

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

Jennifer V., Dacula, US

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

Jay C.

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.

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

Tammy V.

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.

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

Yan C.

Wills is great
The property manager Wills is very responsive. You will like this house. Yan
Stayed 4 nights in Jul 2023

10/10 Excellent

Julita M.

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

10/10 Excellent

ryan f.

nice neighborhood
very nice home well kept up with. 2 min walk to bus and 15 min to train. plenty of space for a family of 6 . thanks will
Stayed 4 nights in Oct 2023

10/10 Excellent

Janis C.

Lake view neighborhood
The online pictures really didn’t do the property justice. It was lovely, clean and comfortable in a safe neighborhood. I love Chicago and would stay there again in a heartbeat.
Stayed 4 nights in Mar 2023

10/10 Excellent

Edwin F T.

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

Jon H.

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

10/10 Excellent

Steph L.

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

Michelle G.

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

10/10 Excellent

Trisha N.

Chicago Gem
This kind host and well-appointed home-away-from-home helped us have a top 10 family reunion vacation.We accessed Chicago's best from here. Our group of 13 needed space to make meals and eat together, play gamesand have separate bedrooms. We couldn't believe our luck when we found this home within walking distance of Lake Michigan, transit and local restaurants. We were delighted by the amount of space, the smart functional layouts of each room, the quality of the furnishings and (for me) the décor and history of the home. It is hard to please 13 people, but we were ALL pleased. In the kitchen, we had all the tools we needed for cooking and serving, and they were good quality. Teflon pans in great condition, good knives, full sets of dishes and glasses, large refrigerator, gas range. The dining table had cloth covered chairs and generous seating. The huge living connected to a charming sunroom featuring two high-top tables, allowing everyone to find favorite spots for eating, conversation or games. The bedding was high quality with comfy sheets and pillows. The laundry room provided space for families to keep up with their wash in newer appliances that worked great. The rooftop provided another great gathering space. It's where we had morning yoga! On the 4th of July, we avoided the crowds and had our own rooftop BBQ. Home and garden decorating details such floral arrangements and giant hostas were icing on the cake for me. Will, our host was incredibly responsive throughout.
Stayed 7 nights in Jul 2023

10/10 Excellent

Verified traveller

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

abhinav d.

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.

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.

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.

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.

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

Jeremy S.

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