Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Photo gallery for Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

A cozy living room with a fireplace, leather sofas, and a dining area with a green wall and large windows.
An outdoor patio with metal tables and chairs, a grill, and a decorative fence.
A two-story building with a beige facade, black-framed windows, and a black metal fence in front.
A kitchen with wooden cabinets, a microwave, a stove, and a sink.
A dining area with a wooden table and patterned chairs, a chandelier, and a plant shelf.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Lake Michigan

Popular amenities

  • Balcony
  • Arcade/game room
  • Barbecue
  • Electric vehicle charging point
  • Pet-friendly
  • Air-conditioning

Explore the area

View map
Chicago, IL
  • Place, Lincoln Park
    ‪3 min walk‬
  • Place, Vic Theatre
    ‪13 min walk‬
  • Place, Wrigley Field
    ‪19 min walk‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪33 min drive‬

Rooms & beds

6 bedrooms (sleeps 20)

Bedroom 1

2 Queen Beds

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Bedroom 5

2 Queen Beds

Bedroom 6

1 King Bed

Common area 1

1 Double Futon

Living Room 3

2 Single Futons

2 bathrooms

Bathroom 1

Bathtub or shower · Bathtub · Toilet · Shower only

Bathroom 2

Bathtub or shower · Bathtub · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Number of living rooms
Outdoor play area
Garden
Dining area

Add dates for prices

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About the area

Chicago

Located in Lakeview, a neighbourhood in Chicago, this holiday home is next to a golf course and on the waterfront. The area's natural beauty can be seen at Lake Michigan and Millennium Park, while Chicago Theatre and Art Institute of Chicago are cultural highlights. Looking to enjoy an event or a game? See what's going on at Wrigley Field or United Center.
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Map
Chicago, IL

What's nearby

  • Lincoln Park - 3 min walk - 0.3 km
  • Vic Theatre - 13 min walk - 1.1 km
  • Wrigley Field - 19 min walk - 1.7 km
  • Theater Wit - 2 min drive - 1.5 km
  • Lincoln Park Zoo - 4 min drive - 2.5 km

Getting around

  • Chicago Clybourn Station - 5 min drive
  • Belmont Station (Red Line) - 13 min walk
  • Chicago Midway Airport (MDW) - 35 min drive

Restaurants

  • ‪The Coffee & Tea Exchange - ‬7 min walk
  • ‪Sushi+ Rotary Sushi Bar - ‬5 min walk
  • ‪DryHop Brewers - ‬3 min walk
  • ‪Wilde Bar & Restaurant - ‬3 min walk
  • ‪Taco Bell - ‬6 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 does it cost to stay at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots?

As of 30 October 2026, prices found for a 1-night stay for 2 adults at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots on 2 February 2027 start from NZ$1,512, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 53 out of 56 reviews
Rating 8 - Good. 3 out of 56 reviews
Rating 6 - Okay. 0 out of 56 reviews
Rating 4 - Poor. 0 out of 56 reviews
Rating 2 - Terrible. 0 out of 56 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was clean, well equipped and very comfortable. Will was very responsive and made the check in and check out process very easy. The location was fantastic and within walking distance of many wonderful restaurants. Great spot for families.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We were really impressed by this place, looks even nicer than the photos! Lots of space for our group, loved the Spanish vibe and outdoor patio.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a family function in Chicago in this house was perfect. Great location with great restaurants and bars nearby. Lots of room for everybody to spread out and we had 11 at the house and did not feel cramped at all. Easy check-in, easy checkout the kitchen is fully stocked and towels are of high-quality.I’d rent this place again, no issues. The large patio above the garage is a bonus.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved this property! So much character and plenty of room. Great location and well stocked. Easy check-in and got good instructions from owner prior to checking in. Lots of games and TVs in all rooms. Highly recommend this place for families especially!!
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house in perfect location. Had everything we needed and so much more.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This place is excellent! I believe we’ve stayed here 4-5 times now and each time they have added a few more little things that just top off your experience. For any of you that rent places, you know that the kitchens can be sparsely equipped… but not this place! They might have more accessories than I have at home. The work group that I travel with drinks a fair bit of coffee and we arrived on this trip to find that the owner had upgraded the coffee maker to a dual pot system! The place has been great from the first visit but the keep making ot feel more like home. Love it!Also, shout out to the people that clean the place! They do an excellent job of keeping it up. We’ll be back!!!Thank you, Jon
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

8/10 Good

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

Wedding weekend

Good location - plenty of room
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house, really enjoyed our stay here! Very comfy, plenty of room, had character and we liked it more than the pictures, and very convenient to get downtown or to Wrigley from. Bus and metro stops are right nearby, and also a short trip on ride-share apps. It's an older house so a bit squeakier in the basement than upstairs, but that's to be expected and I'd happily stay here again on future visits! I really liked the character, style, and location of the house - was very comfortable and we really enjoyed staying here!
Stayed 4 nights in Nov 2025
Verified review

10/10 Excellent

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

Nice Oroperty

Comfortable, spacious, good location.
Stayed 2 nights in Jun 2024
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was immediately responsive, with answers and kindness. Excellent communication.Great place to make memories! My family of six, my sister's family of 5, coming from Chicago, Minneapolis, St. Louis, Indianapolis (area) and Colorado Springs - great place for us all to gather...it was a great location, with lots to see in the neighborhood, as well.House had plenty of space! Plenty of towels, beds, areas to gather, and a well-stocked kitchen.
Stayed 3 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family friendly for group of adults. Great garage rooftop patio to sit and enjoy time together. House has multiple large gathering areas (large dining room table, family room w/ adjacent front room-this has 2 high tops that seat 8, and large basement family room with adjacent game areas, besides the patio). Kitchen is sufficient to facilitate meals, and having a dual 12 cup coffee maker assures you won' run out of coffee quickly in the am for a large group. Location is such that it is located at the end of the block in a relatively quiet neighborhood that you can access the city hustle and bustle by walking a block or 2, but you're buffered from most of the noise. Our group walked to Wrigley Field about a mile plus to the northwest but were able to also walk south to north Lincoln Park too. Like the neighborhood, this home is older, historic with lots of character. Our group had a very nice stay here.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

Fun time

Good time
Stayed 2 nights in Feb 2025
Verified review

8/10 Good

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
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