Title: Book the Best Kenwood LUXURY Hotels - Upscale Hotels in Kenwood, Chicago | 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://mediaim.expedia.com/destination/2/c96faeb4027380ae39b3c345c19d58bf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Marc Jacobs # Find Luxury Hotels in Kenwood, Chicago - ![](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 Luxury Hotels Tonight [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-11-04&endDate=2025-11-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-11-05&endDate=2025-11-06&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-11-14&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Kenwood Luxury Hotels ![Buffet](https://images.trvl-media.com/lodging/1000000/10000/7400/7341/f4afbe6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, eco-friendly toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/10000/7400/7341/c0b18758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/7400/7341/48669158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/7400/7341/5dc5b9fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Lake Shore Hotel Kenwood 6.8/10 (1000) "Clean and good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tori [](https://www.expedia.ca/Chicago-Hotels-Chicago-Lake-Shore-Hotel.h7341.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=2025-11-19&endDate=2025-11-20®ionId=6132343&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Kenwood Hotel Reviews ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "It was great experience but middle of the night there was bagging then sounded like a drill going repairing something " [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "Clean rooms and friendly staff" [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "Great" [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Good service " [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Staff interactions were excellent in every aspect. " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Great staff at the front desk!" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Best upon arrival and the staff promptly answered any and all concerns" [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Palmer House a Hilton Hotel](//images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Room was very clean and well kept" [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Everything was perfect will definitely stay again . " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury getaway to Kenwood? > Let Expedia help you arrange your flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare Intl. Airport (ORD) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to get what you want to make your stay special. If you want an upscale hotel with fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Kenwood offers. Known for its museums and university, Kenwood also has some interesting things to see and do including Lake Michigan, so you may want to take in the local sights during your visit. ### What's there to see and do in Kenwood? > Enjoy Kenwood and visit Lake Michigan, 4944 S Woodlawn Ave, and Obama's House. 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