Title: The Speakeasy on Chicago! - 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 # The Speakeasy on Chicago! Vacation home in Pensacola with kitchen ![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97580000/97575900/97575848/w1440h984x0y1-66d5e141.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Smart TV](https://images.trvl-media.com/lodging/98000000/97580000/97575900/97575848/80a4a60a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV](https://images.trvl-media.com/lodging/98000000/97580000/97575900/97575848/w1440h941x0y0-aa7c1195.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/98000000/97580000/97575900/97575848/46fa170e.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/98000000/97580000/97575900/97575848/w1440h984x0y0-501e5c0b.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location The Speakeasy on Chicago! provides laundry facilities and more. Stay connected with free in-room WiFi. 10 Exceptional ### Entire home 4 bedrooms2 bathroomsSleeps 8 ## Popular amenities - Parking available - Dryer - Washer - Kitchen - Air conditioning - Free WiFi ## 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. ### The Speakeasy on Chicago! Enjoy a quiet location that offers easy access to everything. Pack up the provided beach chairs, beach towels, and beach wagon for fun days in the sun -Perdido Key Beach and Pensacola Reach ran he reached in no timel Your family will be close to everything when you stay at this centrally-located place. ## Property amenities ### Beach - Beach nearby - Beach loungers ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Dishwasher - Microwave - Oven - Stovetop ### Bedrooms - 4 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Bathtub or shower - Hair dryer - Shampoo - Shower - Soap - Toilet paper - Towels provided ### Entertainment - Smart TV ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### 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) - First aid kit - Fire extinguisher - Deadbolt lock ## Similar properties ![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91810000/91803500/91803487/3d5fc2f8.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Close to beaches w/small private beach access across street, partial Gulf View. Pensacola - Ocean view - Kitchen - Washer - Dryer 9.6 Exceptional 31 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&selected=91803487&PinnedHotelID=91803487&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/99000000/98310000/98308800/98308781/e346a811.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Grandma's house is calm and relaxing. Pensacola - Kitchen - Washer - Dryer - Pet-friendly 9.2 Wonderful 7 reviews CA $192 CA $502 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-04&endDate=2025-11-05&selected=98308781&PinnedHotelID=98308781&HadPinnedHotel=true®ionId=-1&adults=2) ![Dining](https://images.trvl-media.com/lodging/90000000/89510000/89506600/89506504/8c784ece.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 10 mins to Five Flags Speedway, Fenced Backyard Northwest Pensacola - Kitchen - Washer - Dryer - Pet-friendly 9.6 Exceptional 5 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&selected=89506504&PinnedHotelID=89506504&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89690000/89684700/89684661/444220f5.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Secluded Waterfront property on Perdido Bay with a dock and private beach Pensacola - Kitchen - Washer - Dryer - Pet-friendly 8.6 Excellent 18 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&selected=89684661&PinnedHotelID=89684661&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116500000/116498500/116498490/0c54728c.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Charming and Spacious Entire House, 3BR/2.5BA located at Pensacola, Florida South Pensacola - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&selected=116498490&PinnedHotelID=116498490&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73290000/73288300/73288295/a60fc809.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cozy Home Near Pensacola &Perdido Key Beaches, Next 2 NAS. Ideal 4Longterm stays Pensacola - Kitchen - Washer - Dryer - Free WiFi 5.6 7 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&selected=73288295&PinnedHotelID=73288295&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/117000000/116650000/116648000/116647978/1cfcb3e9_edited_4b96.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Peaceful Pensacola Home Southeast Pensacola - Kitchen - Washer - Dryer - Free WiFi 9.8 Exceptional 11 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&selected=116647978&PinnedHotelID=116647978&HadPinnedHotel=true®ionId=-1&adults=2) ![TV](https://images.trvl-media.com/lodging/93000000/92080000/92070700/92070672/w1200h899x0y1-982c8937.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Birds of Paradise - 5 min from NAS - 7 min from Downtown Pensacola! Pensacola - Kitchen - Outdoor space - Toys/games 6.8 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&selected=92070672&PinnedHotelID=92070672&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96490000/96484100/96484006/374e3ff7.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Your Dream Vacation Awaits: A Private Poolside Paradise Near Everything! South Pensacola - Pool - Kitchen - Washer - Dryer 8.6 Excellent 11 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&selected=96484006&PinnedHotelID=96484006&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/76000000/75200000/75198900/75198831/b86dedaf.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### D's Florida Vacation Home Pensacola - Kitchen - Washer - Dryer - Free WiFi 9.6 Exceptional 7 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&selected=75198831&PinnedHotelID=75198831&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Minimum check-in age: 18 ### 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 not allowed ### Children and extra beds Children are welcome ### 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 Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock 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 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=30.466272,-87.2937&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:ii%7ExDrpxsO%3FQ%40Q%3FQ%3FS%40Q%40O%40Q%40Q%40S%40QBO%40QBQBQBQBOBSBODQBODQDODQDODOFQDMFQFMFQFMFOFOFMHOFOHMHMFMJMFMJMHKJMHKJMHKJMJKJKJIJKJILKJIJKLGLIJILILGLILGLELILELGLGNELENELELENCLCNENCLCNCNALCNANANCN%3FNALAN%3FN%3FNAN%40L%3FN%3FN%40N%40N%3FNBL%40N%40NBN%40LBNBNBLDNBLBNDLDNDLDLDLFNFLDLHLDLFLHLFJHLHLHJFLJJHJJLHJJJHJJJJHLJJJLHJJLHJHLHLHLHLHLHLFNHNFLFNFNFLFPFLDPFLDPDNFNDPBNDPDNBPDNBRBNBPBP%40PBPBN%40P%40R%40P%40P%40N%3FP%40R%3FP%3FP%3FP%3FP%3FP%3FRAP%3FPANAPARAPAPCNCPARCNCPCNCRENCPEPENCNEPGNEPENGNENGNGNGNGLGNGNILGNILILILILILILILKJILKJKLIJKJKJKHKJMJKHKHMJKFMJMFKHMFMHMFMFMFMDOFMFMDMDODMDODMBODMBOBOBMBOBO%40OBM%3FOBO%40O%3FO%40O%3FM%3FO%40OAO%3FO%3FMAO%3FOAOCO%3FOCMAOCOCMCOCOCMEOCMEMEOEMEOEMGMGMEMGMGMGMIMGMIKGMKMGKKKIMIKKKKKIKKKKKKIMKKIMKKIMKMGMKMGMIMIMGOIMGOGOGMGOGOGOGOEOGOEQEOEQEOEOCQEQCOCSCOCQCOCSAQCOAQAQASAQAOAQ%3FQ%3FSAQ%3FQ&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=8rd2tJl7dFl866VBSq-MAPcBp1s=) Pensacola, FL #### What's nearby - Five Flags Speedway - 6 min drive - 6.8 km - IWTC Corry Station - 11 min drive - 9.6 km - Cordova Mall - 11 min drive - 9.4 km - Pensacola Bay Center - 13 min drive - 14.4 km - Pensacola Naval Air Station - 14 min drive - 12.5 km #### Getting around - Pensacola Station - 8 min drive - Pensacola Intl. Airport (PNS) - 12 min drive #### Restaurants - ‪McDonald's - ‬16 min walk - ‪Whataburger - ‬19 min walk - ‪Circle K - ‬4 min drive - ‪Culver's - ‬18 min walk - ‪Foosackly's - ‬16 min walk ## Frequently asked questions ### Is The Speakeasy on Chicago! pet-friendly? > No, pets are not allowed at this property. ### What time is check-in at The Speakeasy on Chicago! ? > Check-in begins at 4:00 PM. ### What time is check-out at The Speakeasy on Chicago! ? > Check-out is at 11:00 AM. ### Where is The Speakeasy on Chicago! located? > Located in Northwest Pensacola, this vacation home is 2.5 mi (4.1 km) from Fast Eddies Fun Center and 2.9 mi (4.7 km) from Brent Athletic Park. Osceola Municipal Golf Course and Five Flags Speedway are also within 6 mi (10 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## The Speakeasy on Chicago! 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 6 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 9.4/10 Cleanliness ### 10/10 Excellent #### Julie L. Dec 3, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Very Clean House was perfect for our quick trip to visit my son. Very convenient to stores and restaurants nearby. The house was extremely clean. Beds were comfortable. Would stay again. ##### Julie L. Stayed 3 nights in Nov 2023 ### 10/10 Excellent #### Trammell R. Jul 17, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### June family trip The property was clean and well maintained. Any minor issue we had, we sent an email and there was an immediate response. We greatly appreciate the hospitality and will definitely look to utilize the services and location again. ##### Trammell R. Stayed 2 nights in Jun 2024 ### 10/10 Excellent #### kathleen R. Mar 15, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay! The home was perfect and cozy. I would rent this again. 10 stars for sure. ##### kathleen R. Stayed 2 nights in Mar 2025 ### 10/10 Excellent #### Katie T. Aug 12, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Clean property and responsive manager! Very nice house that was close to everything we needed, Corry Station and the beaches! Would recommend to anyone looking :) ##### Katie T. Stayed 3 nights in Aug 2024 ### 10/10 Excellent #### Elijah b. Jul 7, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Amazing The property was spacious and clean! Communication with Me. Nick the house was easy and quick response! All around a great stay! ##### Elijah b. 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