Title: Chicago Bootlegger House Sleeps 11-22 with 3 parking spots - Latest Reviews, Deals & Photos 2025 - Expedia.ca [See all properties](http://www.expedia.ca/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 vacation home with kitchen and balcony ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77990000/77987800/77987740/0473ba28.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Exterior](https://images.trvl-media.com/lodging/78000000/77990000/77987800/77987740/34f3856b.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77990000/77987800/77987740/90eff6c2.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/78000000/77990000/77987800/77987740/2f9efbd9.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77990000/77987800/77987740/c1af4bd7.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location 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. 10 Exceptional ### Entire home 6 bedrooms2 bathrooms ## Popular amenities - - - Dryer - Washer - Pet-friendly - Fireplace ## 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 transportation - 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 - Ice maker - Kitchen island - Microwave - Oven - Paper towels - Refrigerator - Spices - Stovetop - 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 - 2 pets total (up to 50 lbs per pet) ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Housekeeping (limited availability) - Iron/ironing board ### Location highlights - In the city center - 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 ![Exterior](https://images.trvl-media.com/lodging/64000000/63940000/63935500/63935488/f4557ac6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Inspiring Stone Grotto Sleeps 10-20 & Free Parking Lakeview - Kitchen - Washer - Dryer - Pet-friendly 9.8 Exceptional 28 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-08&selected=63935488&PinnedHotelID=63935488&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37150000/37146600/37146543/ff7896b0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Wrigley Field/Lakeview -Entire Home- Large Groups! 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Lakeview - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 24 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-08&selected=67391679&PinnedHotelID=67391679&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 ### Pets Pets allowed Service animals are welcome, and are exempt from fees 2 total (up to 50 lbs 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 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 Onsite parties or group events are strictly prohibited Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property 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 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 - 5 min walk - 0.4 km - Wrigley Field - 19 min walk - 1.7 km - Lincoln Park Zoo - 2 min drive - 2.5 km - Michigan Avenue - 5 min drive - 5.3 km - Navy Pier - 9 min drive - 8.1 km #### 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 - ‪OMi Cafe - ‬3 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 50 lbs per pet. ### 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? > Check-out is at 11:00 AM. ### Where is Chicago Bootlegger House Sleeps 11-22 with 3 parking spots located? > This family-friendly Chicago vacation 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. ## 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 10 ### 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.ca/lp/b/content-guidelines) 10 - Excellent 44 8 - Good 2 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10/10 Cleanliness ### 8/10 Good #### Judy G. Jun 5, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wedding weekend Good location - plenty of room ##### Judy G. Stayed 4 nights in May 2025 ### 8/10 Good #### Robert W. Jul 14, 2025 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. ##### Robert W. Stayed 4 nights in Jul 2025 ### 10/10 Excellent #### Jennifer B. May 19, 2025 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. ##### Jennifer B. Stayed 4 nights in May 2025 ### 10/10 Excellent #### Tony P. Feb 23, 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. Jan 27, 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 #### Leng Y. Mar 1, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Fun time Good time ##### Leng Y. Stayed 2 nights in Feb 2025 ### 10/10 Excellent #### Lisa W. Jan 3, 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 #### Francisco R. Jan 9, 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 #### Barb L. Jun 23, 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 #### Luke W. Sep 23, 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 #### Stefani Z. May 15, 2023 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! ##### Stefani Z. Stayed 4 nights in May 2023 ### 10/10 Excellent #### Steven B. Aug 26, 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 Oct 18, 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 #### Jay C. Apr 8, 2023 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. ##### Jay C. Stayed 2 nights in Apr 2023 ### 10/10 Excellent #### Sarah B. May 25, 2023 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. ##### Sarah B. Stayed 2 nights in May 2023 ### 10/10 Excellent #### Katie G. Apr 28, 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 #### Paul M. Feb 3, 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 #### Tammy V. Jun 27, 2023 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. ##### Tammy V. Stayed 5 nights in Jun 2023 ### 10/10 Excellent #### Nicole S. Jun 18, 2023 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! ##### Nicole S. Stayed 3 nights in Jun 2023 ### 10/10 Excellent #### Jennifer V., Dacula, US Oct 5, 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 #### abhinav d. Oct 9, 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 #### Daniel E. Jan 6, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. ##### Daniel E. Stayed 2 nights in Jan 2025 ### 10/10 Excellent #### Peter V. Apr 7, 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 #### Felicity S. Oct 5, 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 #### Jon H. Sep 13, 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. 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