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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 - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)
Exterior - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)
Interior - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)
Fridge, microwave, oven, stovetop - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)
Outdoor dining - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)
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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  • 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
Information provided by the property may be translated using automated translation tools

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

  • Lincoln Park - 3 min walk - 0.3 km
  • Briar Street Theatre - 8 min walk - 0.7 km
  • Advocate Illinois Masonic Medical Center - 13 min walk - 1.1 km
  • Vic Theatre - 13 min walk - 1.1 km
  • Wrigley Field - 19 min walk - 1.7 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.

How much is parking at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

On-site parking is available at the property.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 45 out of 47 reviews
Rating 8 - Good. 2 out of 47 reviews
Rating 6 - Okay. 0 out of 47 reviews
Rating 4 - Poor. 0 out of 47 reviews
Rating 2 - Terrible. 0 out of 47 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Jon H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just stayed here for the 3rd time! The owner/manager continues to keep the place in great shape and even seems to have added small “niceties” to the property. Many places you stay at over time, start to get “let-go” but this one just gets better. We’ll be looking to book again as soon as our next dates are set!!
Stayed 3 nights in Sep 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

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

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

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

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

Leng Y.

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

Fun time

Good time
Stayed 2 nights in Feb 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

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

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

Stefani Z.

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

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

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

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

10/10 Excellent

Jay C.

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

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

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

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

Tammy V.

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

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, check-in, communication, location, listing accuracy

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

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

Jennifer V., Dacula, US

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

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

Peter V.

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

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

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

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

Yan C.

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

Wills is great

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