See all properties

Bootlegger House Sleeps 10-20 Free TV & Parking

Top rated by guests
Activities, Library, Library, Living room
Library, Library, Living room, Decorative detail
Communal lounge/ TV room
Buffet breakfast, Family
Dining area
review stars
10Outstanding
(4 Ratings)
"We found the property perfect for our family gathering to celebrate a graduation in Chicago. With multiple family members coming to town the home accommodated us wonderfully. We really enjoyed the lar..."
Verified guest
Don't miss out! Price and availability may change
10 / 10
Outstanding(4 Ratings)

Apartment in Chicago, IL

20 guests · 6 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this apartment rental

Offering a garden and a tennis court, Bootlegger House Sleeps 10-20 Free TV & Parking in Chicago is close to Fullerton Beach and Wrigley Field. Guests staying at this apartment have access to a patio.

Amenities at Bootlegger House Sleeps 10-20 Free TV & Parking

Free WiFi/internet
Free Parking
Air conditioning
Non-smoking
Pets allowed
Heating
Balcony/Terrace
WiFi/Internet
Private beach access
Beach access
Garden
Accessible Parking
Electric Vehicle Charging Station
Outdoor Cooking
Family friendly
Smoking allowed
Contactless check-in/out
Fire alarm
Fire extinguisher
Tennis court
Cleaning products

Map of Chicago, IL

city location on map

Nearby attractions

Millennium Park
4 mi
Navy Pier
3.8 mi
Chicago Riverwalk
3.7 mi
Museum of Science and Industry, Chicago
10.7 mi

Ratings and reviews

10 / 10
Outstanding(4 Ratings)
100% verified reviews
10 / 10Outstanding·May 2026
We found the property perfect for our family gathering to celebrate a graduation in Chicago. With multiple family members coming to town the home accommodated us wonderfully. We really enjoyed the large, very well stocked kitchen and large dining table where we shared meals and played games. The living area was also comfortable for late night chats and tv viewing. The spacious and plentiful bedrooms worked great for the different families too. Communication with the host was clear and well organized for entry and checkout. The location was perfect with easy access to Chicago highlights, shopping and restaurants. A great quiet area. Highly recommend a stay here.
Honestly everything was great, especially impressed with how well set up the home and kitchen was. The provided coffee and double carafe coffee machine was very much appreciated.
$$$$
booking logo

FAQs

Does this property follow enhanced cleaning procedures?

Yes, this apartment has implemented enhanced cleaning procedures and processes to keep you healthy and safe.

Is parking included with this apartment?

Parking is not specified as an available amenity at Bootlegger House Sleeps 10-20 Free TV & Parking. For more information, we encourage you to contact the property about where to park.

Is there a pool at this apartment?

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

Is Bootlegger House Sleeps 10-20 Free TV & Parking pet friendly?

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

What amenities are available at Bootlegger House Sleeps 10-20 Free TV & Parking?

We found 21 amenities for this rental. This includes free wifi/internet, free parking, air conditioning, non-smoking, and pets allowed.

Explore similar stays in Chicago

Explore all stays
10 / 10
Outstanding(1 Rating)
7-Bedroom 2-Flat Perfect for Groups — Near Train, Expressway, United Center
House
 in Chicago
20 guests · 7 bedrooms · 3 baths

Indulge in a peaceful retreat at 7-Bedroom 2-Flat Perfect for Groups — Near Train, Expressway, United Center, our elegant House in Chicago. Enjoy amenities including Pets allowed, Family friendly and Non-smoking, and more.

expedia logo
View deal
10 / 10
Outstanding(1 Rating)
7-Bedroom 2-Flat Perfect for Groups — Near Train, Expressway, United Center
House
 in Chicago
20 guests · 7 bedrooms · 3 baths

Experience vacation in Chicago with our House, 7-Bedroom 2-Flat Perfect for Groups — Near Train, Expressway, United Center. Enjoy amenities such as Pets allowed, Family friendly and Non-smoking, and more.

vrbo logo
View deal
9 / 10
Outstanding(2 Ratings)
Inspiring Grotto Sleeps 10-20 Free TV & Parking
Apartment
 in Chicago
20 guests · 4 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · Balcony/Terrace

Indulge in a peaceful retreat at Inspiring Grotto Sleeps 10-20 Free TV & Parking, our elegant Apartment in Chicago. Enjoy amenities including Free Parking, Pets allowed and Tennis court, and more.

booking logo
View deal
10 / 10
Outstanding(182 Ratings)
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
House
 in Chicago
24 guests · 4 bedrooms · 3 baths

Experience vacation in Chicago with our House, Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24. Enjoy amenities such as No pets allowed and Non-smoking, and more.

vrbo logo
View deal
You can save with One Key
7.4 / 10
Good(3 Ratings)
4 Bedroom, Sleeps 20 people!
Apartment
 in Chicago
20 guests · 4 bedrooms · 4 baths

The best choice in Chicago for Apartment, for $680 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

vrbo logo
View deal
10 / 10
Outstanding(183 Ratings)
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
House
 in Chicago
24 guests · 4 bedrooms · 3 baths

Experience the best of Chicago with this House available for $774. This property is equipped with amenities including No pets allowed and Non-smoking, and more.

expedia logo
View deal
9.8 / 10
Outstanding(92 Ratings)
Wrigley Field/Lakeview -Entire Home- Large Groups!
House
 in Chicago
20 guests · 3 bedrooms · 3 baths

House in Chicago, for $762 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

vrbo logo
View deal
You can save with One Key
10 / 10
Outstanding(23 Ratings)
Large, Exquisitely Decorated in Heart of East Lakeview Near Wrigley & Lakefront
Apartment
 in Chicago
20 guests · 4 bedrooms · 2 baths

Soak up the beauty of Chicago in our Apartment, Large, Exquisitely Decorated in Heart of East Lakeview Near Wrigley & Lakefront. With a range of amenities such as Pets allowed, Family friendly and Non-smoking, you'll feel right at home.

vrbo logo
View deal
9.5 / 10
Outstanding(19 Ratings)
City Villa Sleeps 10-20 Free TV & Parking
Apartment
 in Chicago
20 guests · 4 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · Balcony/Terrace

Business stays, family stays, couples stay, getaway vacation, and rental in Chicago at City Villa Sleeps 10-20 Free TV & Parking for $596 for your next trip.

booking logo
View deal
9.8 / 10
Outstanding(31 Ratings)
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
House
 in Chicago
20 guests · 4 bedrooms · 2 baths

This attractive House in Chicago, $666 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

vrbo logo
View deal
10 / 10
Outstanding(92 Ratings)
Wrigley Field/Lakeview -Entire Home- Large Groups!
House
 in Chicago
20 guests · 3 bedrooms · 3 baths

Are you ready to indulge in a relaxing getaway? Our House in Chicago has everything you need for a rejuvenating stay. Treat yourself to Wrigley Field/Lakeview -Entire Home- Large Groups!'s exceptional amenities, such as Pets allowed and Non-smoking.

expedia logo
View deal
9.6 / 10
Outstanding(39 Ratings)
Extra Large Authentic Chicago Graystone walk to Wrigley, Lakefront & Restaurants
Apartment
 in Chicago
20 guests · 3 bedrooms · 2 baths

Experience the best of Chicago with this Apartment available for $737. This property is equipped with amenities including Pets allowed, Family friendly and Non-smoking, and more.

vrbo logo
View deal
9.9 / 10
Outstanding(46 Ratings)
Stone Mansion Sleeps 10-20 Free Parking Near Lake, Red Line and Wrigley
Apartment
 in Chicago
20 guests · 4 bedrooms · 2 baths

Enjoy the best of Chicago in our Apartment, Stone Mansion Sleeps 10-20 Free Parking Near Lake, Red Line and Wrigley. A stunning property with amenities including No pets allowed, Family friendly and Non-smoking, and more.

vrbo logo
View deal
3.6 / 10
(4 Ratings)
Downtown Elmhurst! Where else would you want to be!!
Apartment
 in Elmhurst
6 guests · 2 bedrooms · 1 bath

Experience vacation in Chicago with our Apartment, Downtown Elmhurst! Where else would you want to be!!. Enjoy amenities such as Pets allowed, Family friendly and Non-smoking, and more.

vrbo logo
View deal
10 / 10
Outstanding(23 Ratings)
Large, Exquisitely Decorated in Heart of East Lakeview Near Wrigley & Lakefront
Apartment
 in Chicago
20 guests · 4 bedrooms · 2 baths

Are you ready to indulge in a relaxing getaway? Our Apartment in Chicago has everything you need for a rejuvenating stay. Treat yourself to Large, Exquisitely Decorated in Heart of East Lakeview Near Wrigley & Lakefront's exceptional amenities, such as Pets allowed, Family friendly and Non-smoking.

expedia logo
View deal
You can save with One Key
Historic Hinsdale Long Term Fully Furnished Home
House
 in Hinsdale
4 guests · 2 bedrooms · 2 baths

Business stays, family stays, couples stay, getaway vacation, and rental in Chicago at Historic Hinsdale Long Term Fully Furnished Home for $350 for your next trip.

vrbo logo
View deal
10 / 10
Outstanding(2 Ratings)
Club Salon Sleeps 10-20 Free Parking & TV
Apartment
 in Chicago
20 guests · 3 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · Balcony/Terrace

Experience vacation in Chicago with our Apartment, Club Salon Sleeps 10-20 Free Parking & TV. Enjoy amenities such as Free Parking, Pets allowed and Tennis court, and more.

booking logo
View deal
9 / 10
Outstanding(7 Ratings)
The Ultimate Escape. Unpack, Relax, Enjoy!Sleeps14
House
 in Elmhurst
14 guests · 4 bedrooms · 2 baths

Are you ready to indulge in a relaxing getaway? Our House in Chicago has everything you need for a rejuvenating stay. Treat yourself to The Ultimate Escape. Unpack, Relax, Enjoy!Sleeps14's exceptional amenities, such as Pets allowed, Family friendly and Non-smoking.

vrbo logo
View deal
10 / 10
Outstanding(31 Ratings)
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
House
 in Chicago
20 guests · 4 bedrooms · 2 baths

Discover the beauty of Chicago with a stay at Inspiring Stone Grotto Sleeps 10-20 & Free Parking, a top rated House with amenities such as Pets allowed, Family friendly and Non-smoking, and more.

expedia logo
View deal
You can save with One Key
Lovely Elmhurst Ranch • 4 Beds 2 Baths
House
 in Elmhurst
10 guests · 3 bedrooms · 2 baths

When traveling to Chicago, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $282 per night.

vrbo logo
View deal
4-Bed 2-Bath Ranch Home – No Stairs Easy Living
House
 in Elmhurst
10 guests · 4 bedrooms · 2 baths

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chicago, at $773 per night for your next great vacation.

vrbo logo
View deal
8.8 / 10
Excellent(17 Ratings)
The Skyway - 5+beds
House
 in Bensenville
12 guests · 4 bedrooms · 2 baths

This inviting House in Chicago can fit your needs for many types of vacations, at $451 per night.

vrbo logo
View deal
9.8 / 10
Outstanding(39 Ratings)
Extra Large Authentic Chicago Graystone walk to Wrigley, Lakefront & Restaurants
Apartment
 in Chicago
20 guests · 3 bedrooms · 2 baths

Experience the best of Chicago with this Apartment available for $737. This property is equipped with amenities including Pets allowed, Family friendly and Non-smoking, and more.

expedia logo
View deal
You can save with One Key
10 / 10
Outstanding(2 Ratings)
Elmhurst Gem – Ideal Mid-Term Rental, Top Location
House
 in Elmhurst
7 guests · 3 bedrooms · 1 bath

When traveling to Chicago, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $218 per night.

vrbo logo
View deal
9.5 / 10
Outstanding(2 Ratings)
Stone Mansion Sleeps 10-20 Free TV & Parking
Apartment
 in Chicago
20 guests · 4 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · Bar

Looking for a memorable stay in Chicago? Our Apartment might just be what you're looking for. Enjoy amenities including Free Parking, Pets allowed and Bar, and more during your stay.

booking logo
View deal
10 / 10
Outstanding(28 Ratings)
NEW MODERN HOME CLOSE TO EVERYTHING!
House
 in Elmhurst
10 guests · 5 bedrooms · 2 baths

House in Chicago, for $544 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

vrbo logo
View deal
Newly Remodeled Home w/ Game Room & Amazing Yard
House
 in Elmhurst
6 guests · 3 bedrooms · 2 baths

Are you ready to indulge in a relaxing getaway? Our House in Chicago has everything you need for a rejuvenating stay. Treat yourself to Newly Remodeled Home w/ Game Room & Amazing Yard's exceptional amenities, such as ;.

vrbo logo
View deal
10 / 10
Outstanding(47 Ratings)
Stone Mansion Sleeps 10-20 Free Parking Near Lake, Red Line and Wrigley
Apartment
 in Chicago
20 guests · 4 bedrooms · 2 baths

Looking for the perfect place to call home during your trip to Chicago? This Apartment offers a comfort and style with top-notch amenities, including No pets allowed, Family friendly and Non-smoking, and more.

expedia logo
View deal
You can save with One Key
New Elmhurst Gem|Sleeps 10|Game Room|Near City Ctr
House
 in Elmhurst
8 guests · 3 bedrooms · 2 baths

Business stays, family stays, couples stay, getaway vacation, and rental in Chicago at New Elmhurst Gem|Sleeps 10|Game Room|Near City Ctr for $805 for your next trip.

vrbo logo
View deal
10 / 10
Outstanding(13 Ratings)
Exuberant - Elmhurst Home!
House
 in Elmhurst
10 guests · 4 bedrooms · 2 baths

Looking for the perfect place to call home during your trip to Chicago? This House offers a comfort and style with top-notch amenities, including Pets allowed, Family friendly and Non-smoking, and more.

vrbo logo
View deal