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Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

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

Fridge, microwave, oven, stovetop
Property grounds
Exterior
Iron/ironing board, travel crib, free WiFi, bed sheets
Dining
Reviews
10

Exceptional

Popular amenities

  • DryerDryerDryer
  • Hot TubHot TubHot Tub
  • WasherWasherWasher
  • FireplaceFireplaceFireplace
  • Pet friendlyPet friendlyPet friendly
  • Barbecue grillBarbecue grillBarbecue grill

Explore the area

Map
Chicago, IL
  • Popular LocationLincoln Park5 min walk
  • Popular LocationWrigley Field2 min drive
  • Popular LocationLincoln Park Zoo3 min drive
  • AirportChicago, IL (MDW-Midway Intl.)35 min drive

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

Pool/Spa

  • Spa tub

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • 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
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • Bedsheets provided

Bathroom

  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • 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
  • 2 pets total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Housekeeping (limited availability)
  • Iron/ironing board

Location highlights

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

Things to do

  • Arcade/game room on site
  • Foosball table on site

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Electric car charging station
  • Garden

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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 allowed
Service animals are welcome, and are exempt from fees
2 total (up to 50 lbs 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

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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether 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 R22000081519

About the neighborhood

Chicago

This vacation home is located in Lakeview, a neighborhood in Chicago, and is next to a golf course and on the waterfront. Art Institute of Chicago and Chicago Theatre are cultural highlights, and some of the area's popular attractions include Lincoln Park Zoo and Field Museum of Natural History. Traveling with kids? Make time for Chicago Museum of Science and Industry, or check out an event or a game at Wrigley Field.
Visit our Chicago travel guideOpens in a new window
View more Vacation Homes in ChicagoOpens in a new window

What's nearby

  • Lincoln Park - 5 min walk
  • Wrigley Field - 2 min drive
  • Lincoln Park Zoo - 3 min drive
  • Michigan Avenue - 4 min drive
  • Chicago Riverwalk - 6 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
  • Wake ‘n Bacon - 4 min walk
  • The Bagel Restaurant & Deli - 4 min walk
  • Wilde Bar & Restaurant - 3 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 50 lbs 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?

Check-out is at 11:00 AM.

Where is Chicago Bootlegger House Sleeps 11-22 with 3 parking spots located?

This family-friendly Chicago vacation 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

Rating 10 - Excellent. 24 out of 24 reviews" "
Rating 8 - Good. 0 out of 24 reviews" "
Rating 6 - Okay. 0 out of 24 reviews" "
Rating 4 - Poor. 0 out of 24 reviews" "
Rating 2 - Terrible. 0 out of 24 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Katie G.

Liked: Cleanliness
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

Julita M.

Liked: Cleanliness
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

Peter V., Reno, USA

Liked: Cleanliness
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

Francisco R.

Liked: Cleanliness
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

Michelle G.

Liked: Cleanliness
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

ryan f.

Liked: Cleanliness
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

Jennifer V., Dacula, US

Liked: Cleanliness
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

Jon H.

Liked: Cleanliness
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

Edwin F T.

Liked: Cleanliness
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

Yan C.

Liked: Cleanliness
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

Trisha N.

Liked: Cleanliness
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

Tammy V.

Liked: Cleanliness
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
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

Sarah B.

Liked: Cleanliness
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

Stefani Z.

Liked: Cleanliness
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
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

Janis C.

Liked: Cleanliness
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

Steph L.

Liked: Cleanliness
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

Zach T.

Liked: Cleanliness
Amazing
The owner was wonderful across the board. He was helpful, attentive and genuinely just very pleasant. The home is beautiful and has really everything you could need. Would recommend to a friend for sure.
Stayed 3 nights in Sep 2022

10/10 Excellent

Clayton M.

Liked: Cleanliness
Chi town sports weekend
Great location 20 minute walk to Wrigley filed, short drive to Soldier field. Nice neighborhood and the house had plenty of space to hangout. The back deck is perfect in good weather!
Stayed 3 nights in Sep 2022

10/10 Excellent

Gregory S.

Liked: Cleanliness
Great place and helpful owner
The property was great! It had plenty of amenities and the patio space is fantastic. The owner was great as well, he helped us with the Wi-Fi when it went down.
Stayed 3 nights in Aug 2022

10/10 Excellent

Keith D.

Liked: Cleanliness
Great location and great house
We enjoyed the large tvs, tables, and foosball table. Very clean. Located to many restaurants and bars. Would highly recommend
Stayed 2 nights in Jul 2022

10/10 Excellent

Connor H.

Liked: Cleanliness
Nice Place
Would've been absolutely perfect if the full bachelor party was able to join. A little spendy with the 6-person group we had. But overall location was great and everyone was comfortable with where we stayed/slept/ate. Would definitely go again with the right sized group.
Stayed 2 nights in Jun 2022

10/10 Excellent

Jon A.

Liked: Cleanliness
Lakeview East VRBO
Awesome location with plenty of room to host a big crew. Garage and patio was very helpful too. Very easy process.
Stayed 2 nights in Jun 2022