Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

5.0 / 5.0

Outstanding(32 Ratings)

House in Chicago, IL

20 guests · 7 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Free cancellationFull refund if you change your mind

Great for petsBring all your friends and family, even the furry ones

About this house rental

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.

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Parking

Laundry

Balcony or Patio

Dishwasher

Garden

Family friendly

Map of Chicago, IL

Nearby attractions

Museum of Science and Industry, Chicago

17.1 mi

RRRR

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

RRRR

5.0 / 5.0

Outstanding(32 Ratings)

House in Chicago, IL

20 guests · 7 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Free cancellationFull refund if you change your mind

Great for petsBring all your friends and family, even the furry ones

About this house rental

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Parking

Laundry

Balcony or Patio

Dishwasher

Garden

Family friendly

Map of Chicago, IL

Nearby attractions

Museum of Science and Industry, Chicago

17.1 mi

Ratings and reviews

5.0 / 5.0

Outstanding(32 Ratings)

5.0 / 5.0

Sep 2024

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

5.0 / 5.0

Aug 2024

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.

5.0 / 5.0

Jul 2024

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!

5.0 / 5.0

Jun 2024

Comfortable, spacious, good location.

5.0 / 5.0

Apr 2024

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.

5.0 / 5.0

Apr 2024

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.

5.0 / 5.0

Apr 2024

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!

5.0 / 5.0

Jan 2024

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.

5.0 / 5.0

Nov 2023

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

5.0 / 5.0

Oct 2023

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

5.0 / 5.0

Oct 2023

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!

5.0 / 5.0

Sep 2023

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…

5.0 / 5.0

Sep 2023

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.

5.0 / 5.0

Jul 2023

The property manager Wills is very responsive. You will like this house. Yan

5.0 / 5.0

Jul 2023

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.

5.0 / 5.0

Jun 2023

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.

5.0 / 5.0

Jun 2023

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!

5.0 / 5.0

May 2023

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.

5.0 / 5.0

May 2023

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!

5.0 / 5.0

Apr 2023

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.

5.0 / 5.0

Mar 2023

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.

5.0 / 5.0

Jan 2023

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.

5.0 / 5.0

Sep 2022

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.

5.0 / 5.0

Sep 2022

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!

5.0 / 5.0

Aug 2022

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.

5.0 / 5.0

Jul 2022

We enjoyed the large tvs, tables, and foosball table. Very clean. Located to many restaurants and bars. Would highly recommend

5.0 / 5.0

Jul 2022

Nice Place

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.

5.0 / 5.0

Jun 2022

Lakeview East VRBO

Lakeview East VRBO

Awesome location with plenty of room to host a big crew. Garage and patio was very helpful too. Very easy process.

FAQs

How much does this house cost compared to others in Chicago?

The average price for a rental in Chicago is R 3,097 per night. This rental is R 6,838 above the average.

Is parking included with this house?

Yes, parking is listed as an amenity at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Chicago Bootlegger House Sleeps 11-22 with 3 parking spots pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

We found 12 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and fireplace.

Explore similar vacation rentals in Chicago

Explore all rentals in Chicago

4.9 / 5.0

Outstanding(1,008 Ratings)

The Peninsula Chicago

Hotel

in Chicago

5star

2 guests · 1 bedroom · 1 bath

Pool · Air conditioner · Internet / Wifi

Nestled in Chicago, this Hotel is perfect for your next vacation. Enjoy The Peninsula Chicago's top-rated amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

RRRR

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

House in Chicago, IL

Reasons to book

About this house rental

Amenities

Map of Chicago, IL

Nearby attractions

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

House in Chicago, IL

Reasons to book

About this house rental

Amenities

Map of Chicago, IL

Nearby attractions

Ratings and reviews

FAQs

How much does this house cost compared to others in Chicago?

Is parking included with this house?

Is there a pool at this house?

Is Chicago Bootlegger House Sleeps 11-22 with 3 parking spots pet friendly?

What amenities are available at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

Explore similar vacation rentals in Chicago

Chicago travel inspiration

Related vacation destinations