See all properties
Save
Entire home

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
Exterior
6 bedrooms, iron/ironing board, travel cot, free WiFi
Interior
Outdoor dining

Reviews

10 out of 10
Exceptional

Entire home

6 bedrooms2 bathrooms

Popular amenities

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

Explore the area

Map
Chicago, IL
  • Wrigley Field
    ‪2 min drive‬
  • Lincoln Park Zoo
    ‪3 min drive‬
  • Michigan Avenue
    ‪4 min drive‬
  • Chicago, IL (MDW-Midway Intl.)
    ‪35 min drive‬

Room options

You may also like

Ad
Exterior

Omni Chicago Hotel

Downtown Chicago
  • Pet-friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
4.5 out of 5, Wonderful, 1,437 reviews
The price is AU$389
includes taxes & fees
27 Mar - 28 Mar
Omni Chicago Hotel

About the area

Chicago

A family-friendly stay in the heart of Chicago awaits you at this holiday home. You'll be 1.8 km (1.1 mi) from Wrigley Field and 2.9 km (1.8 mi) from Lake Michigan. Highlights at this holiday home include a kitchen, a washing machine and free WiFi. .Home features 2 bathrooms, a fireplace and a balcony. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a dining area and a fenced private garden are also available. Limited housekeeping is available. .This pet-friendly holiday home offers a games room, a garden and barbecues. .Attractions within a 10-minute drive of this Lakeview holiday home include Michigan Avenue and Grant Park.
View more Holiday homes in ChicagoOpens in a new window

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
  • Michigan Avenue - 4 min drive - 5.1 km
  • Navy Pier - 7 min drive - 7.6 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

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

Similar properties

Interior

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

  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
5.0 out of 5, Exceptional, 124 reviews
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

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

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 welcome
  • Maximum 2 (weight limit: 50 lb per pet)
    • Service animals are exempt from fees.
  • 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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in all accommodation.

Property Registration Number R24000123644

Frequently asked questions

Are there any beaches close to Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

The closest beach to Chicago Bootlegger House Sleeps 11-22 with 3 parking spots is North Avenue Beach (3 km).

Does Chicago Bootlegger House Sleeps 11-22 with 3 parking spots have a pool?

No, this holiday home doesn't have a pool.

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

You bet! With amenities such as a playground and an arcade, as well as highchairs and travel cots, it's no surprise that Chicago Bootlegger House Sleeps 11-22 with 3 parking spots is a winner with our family travellers.

Is there a free airport shuttle available at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

No, Chicago Bootlegger House Sleeps 11-22 with 3 parking spots does not offer an airport shuttle service.

What time are check-in & check-out at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

Check-in begins at 3:00 PM. Check-out time is 11:00 AM.

Is there a golf course on site at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

There is a golf course next to Chicago Bootlegger House Sleeps 11-22 with 3 parking spots.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 41 out of 41 reviews
Rating 8 - Good. 0 out of 41 reviews
Rating 6 - Okay. 0 out of 41 reviews
Rating 4 - Poor. 0 out of 41 reviews
Rating 2 - Terrible. 0 out of 41 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Leng Y.

Liked: Cleanliness
Fun time
Good time
Stayed 2 nights in Feb 2025

10/10 Excellent

Tony P.

Liked: Cleanliness
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

Paul M., Redmond, Washington

Liked: Cleanliness
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

Susan P.

Liked: Cleanliness
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

Carl W.

Liked: Cleanliness
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

Michelle R.

Liked: Cleanliness
Classy and Convenient!!
First of all, this property was sooooo easy to travel to. I dont mind city driving, but I do get nervous driving downtown. It was so SIMPLE, literally fool proof!! Conveniently located a few blocks from 41 made for a stress-free 15 minute drive to Shedd Aquarium.The house is absolutely beautiful and in a great neighborhood. The property was very secure, neighbors were friendly, and tons of great places within walking distance. Gorgeous original architecture, built ins and stained glass. The interior is well furnished and nicely decorated. Beds and bedding were very comfortable. The house was filled with entertainment - several tv's, games, foosball, etc. It was too cold to enjoy the deck, but it looked like it could be a lot of fun in the warmer months. We have family in Chicagoland and surrounding areas and we will definitely be booking with Will again!!!
Stayed 2 nights in Jan 2025

10/10 Excellent

Daniel E.

Liked: Cleanliness
Perfect for a bachelor party
Stayed for a bachelor party. Nice neighborhood, short walk to wrigley with bars along the way to stop at. Only annoying thing was parking. While there is 3 spots (2 car garage, plus 1 on the small apron in front of the garage) you can not park more than 1 bigger vehicle there so we had to use the parking garage nearby. Luckily it was only 25/day.
Stayed 2 nights in Jan 2025

10/10 Excellent

Lisa W.

Liked: Cleanliness
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

Maureen C., Bettendorf, Iowa

Liked: Cleanliness
Great find.
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.
Stayed 2 nights in Dec 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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

10/10 Excellent

Barb L.

Liked: Cleanliness
Nice Oroperty
Comfortable, spacious, good location.
Stayed 2 nights in Jun 2024

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