Lake View East Rentals USA Illinois Chicago Lake View East

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots | House in Chicago

10.0 (45 Reviews) |   Pet Friendly   6 Bedrooms  2 Bathrooms  20 Guests  Stay&Play
Lake View East House | Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

6 Bedroom House in Lake View East, Chicago

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.

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots is located in Lake View East. Chicago Bootlegger House Sleeps 11-22 with 3 parking spots provides accommodation, featuring Fireplace/Heating, Entertainment, TV, among other amenities. This House features Fireplace/Heating, Entertainment, TV, to make your stay a comfortable one.

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots has 6 Bedrooms , 2 Bathrooms, and max occupancy of 20 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Lake View East has interesting places to visit. If you want to learn more about the House in Lake View East, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • TV
  • View
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 3:00 pm
Check-out Check-out before 11:00 am
Child Policy Children are welcome. note from host: we have a baby crib, bed rail and stroller
Pet Policy 2 total (up to 50 lbs per pet) note from host: walk your pet off the property to eliminate waste pets allowed service animals are welcome, and are exempt from fees
Smoking Policy Smoking is not permitted
Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited property registration number r24000123644 special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
 
Chicago, 60657, USA

What Our Guests say 500 + Reviews

Jun 6, 2025 12:03:47 AM
Summary: Good location - plenty of room
Judy G. Judy G.
May 20, 2025 01:58:05 AM
Summary: We had a fabulous time and enjoyed our stay very much. Will was very helpful and went above and beyond to accommodate our needs.
Jennifer B. Jennifer B.
Mar 1, 2025 08:54:54 AM
Summary: Good time
Leng Y. Leng Y.
Feb 23, 2025 02:54:18 PM
Summary: This is one of the best rentals I've stayed at. Clean, well located and priced well. Would definitely recommend.
Tony P. Tony P.
Feb 4, 2025 01:39:42 AM
Summary: 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 !
Paul M. Paul M.
Jan 27, 2025 11:17:47 PM
Summary: Very comfortable and welcoming. a great stay for a large family. We enjoyed everything about our stay. Will be back!
Susan P. Susan P.
Jan 27, 2025 02:33:51 AM
Summary: Houseowner was very accommodating. Everything was just as it appeared online. Definitely would stay there if ever in chicago again
Carl W. Carl W.
Jan 20, 2025 10:43:40 AM
Summary: 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!!!
Michelle R. Michelle R.
Jan 6, 2025 08:08:16 AM
Summary: 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.
Daniel E. Daniel E.
Jan 4, 2025 02:48:04 AM
Summary: 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.
Lisa W. Lisa W.

FAQ's

Is this Lake View East house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Lake View East house have a swimming pool?

No, this Lake View East house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Lake View East house?

Best-rates for the Lake View East house starts from $730 per night with includes Sports/Activities, Barbecue/Outdoor Cooking, Internet, Kitchen, Laundry, Air Conditioner, Parking, Ocean View, Balcony/Terrace, Child Friendly, Bedding/Linens, Wellness Facilities, Fireplace/Heating, Entertainment, TV, View, Oceanfront, Security/Safety, Pet Friendly StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Lake View East house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Lake View East house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Lake View East house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Lake View East house?

Based on the information reported by the owner or manager, the Lake View East house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Lake View East house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Lake View East house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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