Title: Book the Best Kenwood Hotels with FREE PARKING in 2026 | Expedia.ca [Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Kenwood Car Rentals](https://expedia.ca/Car-Rentals-In-Kenwood.d6132343.Car-Rental-Guide)[Kenwood Vacations](https://expedia.ca/Kenwood.d6132343.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/829/94662344-53ef-4f49-b2be-cb6f7f2e4498.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Free Parking in Kenwood, IL from CA $105 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Kenwood Hotels with Free Parking Tonight [Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-12-10&endDate=2025-12-11&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-12-11&endDate=2025-12-12&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Kenwood hotels with parking ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/5132819a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freehand Chicago Downtown Chicago 8.0/10 Very good (2634) "The room was spotless and the staff where great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $83 CA $122 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/2866aa1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago 9.4/10 Exceptional (2267) "Smooth check in and beautiful hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Monique CA $124 CA $192 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/04b62050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/b0f5bd1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/c5cac7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silversmith Hotel Chicago Downtown Downtown Chicago 9.2/10 Wonderful (2109) "Great hotel. Very affordable for such a perfect location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $112 CA $174 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/50be090a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Downtown Chicago 8.6/10 Excellent (2947) "Great location and great staff!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) lynne CA $107 CA $125 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/0f103d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/3b2677cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/6dc8c836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown South Loop Downtown Chicago 8.8/10 Excellent (1751) "Clean and staff was courteous. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) HANNAH CA $99 CA $116 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/06b28362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Magnificent)](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile Downtown Chicago 9.0/10 Wonderful (3136) "Amazing and will be staying again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angie CA $133 CA $156 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/4844f60a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/edbd6260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/w1584h1367x232y0-cd23229b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/0afe31db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cambria Hotel Chicago Loop - Theatre District Downtown Chicago 8.8/10 Excellent (1451) "Clean, modern, friendly/helpful staff, the perfect spot for staying for a show at The Chicago Theatre. Parking was close and easy too. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan CA $125 CA $147 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Chicago-Hotels-Cambria-Hotel-Chicago-Loop-Theatre-District.h18057374.Hotel-Information) ![American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/ab309a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/36960d65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/64fc97f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/69e6751f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Godfrey Hotel Chicago Downtown Chicago 8.6/10 Excellent (1919) "Good value, great cleaning staff " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) farzana CA $132 CA $187 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/2489547a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/3be95933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/63f719c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/17f1a3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Saint Clair- Magnificent Mile Downtown Chicago 8.4/10 Very good (1789) "Great stay in a great area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giselle CA $88 CA $105 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Chicago-Hotels-The-St-Clair-Hotel-Magnificent-Mile.h49985.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Single Beds](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/6d4883c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/511c43ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Hotel Downtown Chicago 8.8/10 Excellent (4842) "Location of the Hotel is very nice and the hotel is very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Khaing CA $107 CA $125 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-24&endDate=2025-12-25®ionId=6132343&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## Top Kenwood Hotel Reviews ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "My 2nd time coming to Chicago from miami love it in Chicago my favorite hotel " [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "Overall stay was great! The staff and valet were very polite. My only complaint is there was hair in the shower when we checked in. Cleanliness there could be improved. I just washed it down the drain but it wasn’t pleasant to see. Otherwise, the hotel was very nice, close to many things & valet was quick to return our car to us. I’d stay here again. " [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "The front desk staff are WONDERFUL !!! the rooms are super comfortable!" [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Yes" [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Very clean room, great breakfast, and very quick response to request for extra blankets." [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg) ### Crowne Plaza Chicago West Loop by IHG 10/10 Excellent "The staff was wonderful, and my room was neat and clean. My stay was very good." 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