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
Add dates for prices
Property amenities
Beach
Beach nearby
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
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
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
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
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
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 indicated there is a carbon monoxide detector on the property
Host has indicated 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 neighborhood
Chicago, IL
What's nearby
Lincoln Park - 5 min walk - 0.5 km
Wrigley Field - 2 min drive - 1.8 km
Lincoln Park Zoo - 3 min drive - 2.8 km
DePaul University-Lincoln Park - 3 min drive - 2.8 km
Michigan Avenue - 4 min drive - 5.1 km
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 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.
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Chicago Bootlegger House Sleeps 11-22 with 3 parking spots Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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.
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.
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!
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!
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.
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!
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.
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.
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!
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.
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.
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.
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…
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.
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
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.
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.
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
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.
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.
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
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.