Title: Chicago Bootlegger House Sleeps 11-22 with 3 parking spots Reviews, Deals & Photos 2026 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) 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)](https://images.trvl-media.com/lodging/78000000/77990000/77987800/77987740/0473ba28.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, oven, stovetop - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)](https://images.trvl-media.com/lodging/78000000/77990000/77987800/77987740/90eff6c2.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)](https://images.trvl-media.com/lodging/78000000/77990000/77987800/77987740/2f9efbd9.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)](https://images.trvl-media.com/lodging/78000000/77990000/77987800/77987740/34f3856b.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Outdoor dining - Chicago Bootlegger House Sleeps 11-22 with 3 parking spots (Chicago)](https://images.trvl-media.com/lodging/78000000/77990000/77987800/77987740/c1af4bd7.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies 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 Exceptional ### Entire home 6 bedrooms2 bathrooms ## Popular amenities - Kitchen - Washing machine - Dryer - Pet-friendly - Air-conditioning ## Add dates for prices Check-in Check-out Travellers ## 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 - Iron/ironing board - Limited housekeeping ### 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 ## Similar properties ![Property grounds](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/bb724005.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Walk to Wrigley Field! 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Belmont Cragin - Kitchen - Washing machine - Dryer - Pet-friendly 10 Exceptional 9 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-14&endDate=2026-01-15&selected=108576271&PinnedHotelID=108576271&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking. 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](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=41.936775,-87.645096&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:%7Ds%7E%7EFzd%7DuO%3FU%3FU%40S%3FS%40U%3FU%40S%40S%40UBU%40SBSBSBU%40SBSDSBSDSBSDSDSDQDSDSFQDSFQDQFSFQFQHOFQFQHQHOFQHMHQHOHOJMHOJOHMJMJOJMJMHKLMJKJMLKJKLIJKLKLILILIJILINGLILGLENGLGLGNELENELENELCNENCLCNANCNANCL%3FNANANAN%3FN%3FN%3FL%3FN%40N%40N%40L%3FNBN%40NBN%40LDN%40NDLBNDNDLDLDNDLFNFLFLDLFNHLFLHJHLHLHLHLJJJLHJJLJJLJJLLHJJLLLHNJLHLJNHNJLHNHNHPHLFPHNHPFPFPHNFPFPFRDPFPFRDPDRDRDPDRDRBRDRBRDRBRBR%40TBRBR%40RBT%40T%40R%40R%3FT%40T%40R%3FR%3FT%3FT%3FR%3FT%3FRARAT%3FTATAPATCTARCRCRATCRCRETCPERCREREREPEREREPGRGPERGPGPGPINGRGNIPINGPILIPININKNILKNILKLINMLKLILMJKJKLMJKJMHKJMJMHMHMHKHMHMFOHMFMFMDOFMFODMDMDODODMDOBO%40MDO%40OBO%40OBM%3FO%40O%40O%40M%3FO%3FO%3FO%3FOAOAOAM%3FOCOAOCOAMCOCOCMEOEMEOEMEOEMGMGOEMGMGMIOGMIKIMIMIMIMKKKMIKKMKKMKKMKIMKMKMKOKMIMKOIMKOIOIOIQIMGQIOIQGOGSIOGQGQGQESGQESGQESESEQESESCSESCQEUCSASCUCSCSASCUAUAQAU%3FUAU%3FSAS%3FU%3FS&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=WQ_vIZbb8FcG8qxgHn3-n08x1wk=) Chicago, IL #### What's nearby - Lincoln Park \- 3 min walk \- 0.2 miles - Briar Street Theatre \- 8 min walk \- 0.5 miles - Vic Theatre \- 13 min walk \- 0.7 miles - Wrigley Field \- 19 min walk \- 1.0 mile - DePaul University-Lincoln Park \- 2 min drive \- 1.3 miles #### 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? ### How much is parking at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots? ### What time is check-in at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots? ### What time is check-out at Chicago Bootlegger House Sleeps 11-22 with 3 parking spots? ### Where is Chicago Bootlegger House Sleeps 11-22 with 3 parking spots located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Chicago Bootlegger House Sleeps 11-22 with 3 parking spots Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.co.uk/lp/b/content-guidelines) 10 - Excellent 45 8 - Good 2 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 9.8 Location ## Reviews ### 8/10 Good #### Judy G. 5 Jun 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wedding weekend Good location - plenty of room ##### Judy G. Stayed 4 nights in May 2025 ### 10/10 Excellent #### Tony P. 23 Feb 2025 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. ##### Tony P. Stayed 4 nights in Feb 2025 ### 10/10 Excellent #### Susan P. 27 Jan 2025 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! ##### Susan P. Stayed 2 nights in Jan 2025 ### 10/10 Excellent #### Francisco R. 9 Jan 2024 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. ##### Francisco R. Stayed 4 nights in Jan 2024 ### 10/10 Excellent #### Leng Y. 1 Mar 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Fun time Good time ##### Leng Y. Stayed 2 nights in Feb 2025 ### 10/10 Excellent #### Barb L. 23 Jun 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Nice Oroperty Comfortable, spacious, good location. ##### Barb L. Stayed 2 nights in Jun 2024 ### 10/10 Excellent #### Lisa W. 3 Jan 2025 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. ##### Lisa W. Stayed 2 nights in Jan 2025 ### 10/10 Excellent #### Luke W. 23 Sept 2024 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. ##### Luke W. Stayed 3 nights in Sep 2024 ### 10/10 Excellent #### Steven B. 26 Aug 2024 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. ##### Steven B. Stayed 6 nights in Aug 2024 ### 10/10 Excellent #### Verified traveller 18 Oct 2024 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. ##### Verified traveller Stayed 3 nights in Oct 2024 ### 10/10 Excellent #### Katie G. 28 Apr 2024 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. ##### Katie G. Stayed 2 nights in Apr 2024 ### 10/10 Excellent #### Jennifer V., Dacula, US 5 Oct 2023 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! ##### Jennifer V. Stayed 2 nights in Oct 2023 ### 10/10 Excellent #### Peter V. 7 Apr 2024 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! ##### Peter V. Stayed 2 nights in Apr 2024 ### 10/10 Excellent #### abhinav d. 9 Oct 2024 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 ##### abhinav d. Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### Paul M. 3 Feb 2025 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 ! ##### Paul M. Stayed 5 nights in Jan 2025 ### 10/10 Excellent #### Maureen C. 28 Dec 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. ##### Maureen C. Stayed 2 nights in Dec 2024 ### 10/10 Excellent #### Jon H. 13 Sept 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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 ##### Jon H. Stayed 4 nights in Sep 2024 ### 10/10 Excellent #### Felicity S. 5 Oct 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. ##### Felicity S. Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### Edwin F T. 2 Sept 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### The Best Private Accommadations We Ever Stayed At Starting with the owner who was one of the best I have ever worked with, he promptly return all my calls, knew the area, was always accommodating, and was a professional at all times. The house was awesom, fully equipped with the best of appliances, had a large amount of kitchen ware, a large amount of bathroom supplies,bed linens and towels were plentiful, and there were many board games to playl The house was spotless. The decor was beautiful. Excellent location. Everyone in our party said they would highly recommend this property to stay at. ##### Edwin F T. Stayed 4 nights in Aug 2023 ### 10/10 Excellent #### Julita M. 15 Apr 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. ##### Julita M. Stayed 2 nights in Apr 2024 ### 10/10 Excellent #### Jon H. 14 Sept 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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… ##### Jon H. Stayed 3 nights in Sep 2023 ### 10/10 Excellent #### Michelle R. 20 Jan 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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!!! ##### Michelle R. Stayed 2 nights in Jan 2025 ### 10/10 Excellent #### Michelle G. 1 Nov 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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 ##### Michelle G. Stayed 3 nights in Oct 2023 ### 10/10 Excellent #### Jon H. 11 Sept 2025 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!! ##### Jon H. Stayed 3 nights in Sep 2025 ### 10/10 Excellent #### Donald K. 24 Sept 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy A unique property in a very safe, friendly neighborhood. The house was lovely, clean, in excellent repair with lots of room, beds, chairs, TVs, dining area, rooftop patio and everything you could possibly need. Walkable neighborhood with many places to eat and get groceries. Walked and took the bus. Garage was plenty big. Park your car and get out and see the city. ##### Donald K. 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