Title: Book the Best Oakland LUXURY Hotels - Upscale Hotels in Oakland, 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)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d6132392.Car-Rental-Guide)[Oakland Vacations](https://expedia.ca/Oakland.d6132392.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Luxury Hotels in Oakland, Chicago ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Oakland Luxury Hotels Tonight [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-10-01&endDate=2025-10-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-10-02&endDate=2025-10-03&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Luxury Hotels ## Top Oakland Hotel Reviews ![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 "Staff was excellent. Decor was very elegant and classy. Enjoyed my two nights here." [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.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 "Great location to and walking to riverwalk, millennium park. Metro is right outside the front door. " [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.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 "Clean rooms, great staff, everything in walking distance from hotel. Would stay here again. " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "someone smoked as the mattress smelled of smoke. luggage rack is broken" [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](//images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "Outstanding place to stay in downtown Chicago " [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Very Clean Hotel, me and my friend enjoyed our stay here. It is an older hotel but the room was really nice " [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Rooms were clean and staff were always happy to help " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.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 "Great property with great staff and amenities. " [](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 "We had a fantastic stay at the Embassy Suites by Hilton Chicago Downtown River North. Our suite was impressively clean and offered plenty of space to spread out, which made it especially comfortable for a multi-day visit. Everything felt well maintained and tidy, which gave us peace of mind right from the start. The location was another highlight. Being in River North meant we were close to great restaurants, shopping, and attractions, and having the subway nearby made getting around the city easy and convenient. It was the perfect base for exploring Chicago. Breakfast was outstanding and far above the standard hotel fare. There were lots of options to choose from, including fresh fruit, pastries, hot items, and the standout feature—a station for custom-made omelets. It was a great way to start each day, and the variety meant there was something for everyone. Overall, Embassy Suites River North checked all the boxes: clean, spacious, well-located, and with excellent breakfast to top it off. We would happily stay here again on our next trip to Chicago." [](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 holiday in Oakland? > Use Expedia to arrange your flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare Intl. Airport (ORD) airport, and then select from a variety of places to stay that will deliver the luxury you want. 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 Oakland offers. Oakland has some interesting things to see and do including Lake Michigan and 41st Street Beach, so you might want to take in the local sights during your visit. ### What's there to see and do in Oakland? > Take in some sights and attractions while you're in Oakland by visiting Lake Michigan, Navy Pier, and Michigan Avenue. If you have some spare time during your trip, you might want to check out Wrigley Field and Soldier Field. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [Boutique Hotels in Armour Square](https://www.expedia.ca/Armour-Square-Chicago-Hotels-Boutique-Hotel.0-n6132365-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Armour Square](https://www.expedia.ca/Armour-Square-Chicago-Hotels-Cheap-Hotels.0-n6132365-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Armour Square](https://www.expedia.ca/Armour-Square-Chicago-Hotels-Historic-Hotel.0-n6132365-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Armour Square](https://www.expedia.ca/Armour-Square-Chicago-Hotels-LGBT-Friendly-Hotel.0-n6132365-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Armour Square Hotels](https://www.expedia.ca/Armour-Square-Chicago-Hotels.0-n6132365-0.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Beach-Hotel.0-n6132245-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Cheap-Hotels.0-n6132245-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Family-Hotel.0-n6132245-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Historic-Hotel.0-n6132245-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Luxury-Hotel.0-n6132245-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Bronzeville Hotels](https://www.expedia.ca/Bronzeville-Chicago-Hotels.0-n6132245-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Apart-Hotels.d6213376-aaApartHotels.Travel-Guide-Accommodation) - [Chalets in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Chalets.d6213376-aaChalets.Travel-Guide-Accommodation) - [Hotels near Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Hotels.d6213376.Travel-Guide-Hotels) - [Inns in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Inns.d6213376-aaInns.Travel-Guide-Accommodation) - [Resorts in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Resort-Hotels.d6213376-aaResortHotels.Travel-Guide-Accommodation) - [B&B in Chicago 47th Street Station](https://www.expedia.ca/Chicago-47th-Street-Station-Bed-And-Breakfast.d6212783-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Chicago 47th Street Station](https://www.expedia.ca/Chicago-47th-Street-Station-Hotels.d6212783.Travel-Guide-Hotels) - [Guest Houses in Chicago 51st-53rd Street Station](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Guest-Houses.d6212787-aaGuestHouses.Travel-Guide-Accommodation) - [Hotels near Chicago 51st-53rd Street Station](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Hotels.d6212787.Travel-Guide-Hotels) - [Resorts in Chicago 51st-53rd Street Station](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Resort-Hotels.d6212787-aaResortHotels.Travel-Guide-Accommodation) - [Business Hotels in Chicago](https://www.expedia.ca/Chicago-Hotels-Business-Hotel.0-0-d178248-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Chicago](https://www.expedia.ca/Chicago-Hotels-Couples-Resorts-Hotels.0-0-d178248-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Green Hotels in Chicago](https://www.expedia.ca/Chicago-Hotels-Green-Sustainable.0-0-d178248-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Chicago](https://www.expedia.ca/Chicago-Hotels-Hotels-With-A-Lazy-River.0-0-d178248-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Chicago](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Bar.0-0-d178248-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Chicago](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Childcare.0-0-d178248-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Chicago](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Tennis-Courts.0-0-d178248-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Chicago](https://www.expedia.ca/Chicago-Hotels-Mountain-Hotels.0-0-d178248-tMountainHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Chicago](https://www.expedia.ca/Chicago-Hotels-Shopping-Hotel.0-0-d178248-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Chicago](https://www.expedia.ca/Chicago-Hotels-Ski-Hotel.0-0-d178248-tSkiHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Chicago](https://www.expedia.ca/Chicago-Hotels-Wedding-Hotels.0-0-d178248-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Chicago](https://www.expedia.ca/Chicago-Hotels-Winery-Hotel.0-0-d178248-tWineryHotel.Travel-Guide-Filter-Hotels) - [Chicago Hotels](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Lgbt Friendly Hotels in Dearborn Homes](https://www.expedia.ca/Dearborn-Homes-Chicago-Hotels-LGBT-Friendly-Hotel.0-n6132366-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Douglas](https://www.expedia.ca/Douglas-Chicago-Hotels-Adults-Only-Resorts.0-n6132367-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Douglas](https://www.expedia.ca/Douglas-Chicago-Hotels-Beach-Hotel.0-n6132367-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Douglas](https://www.expedia.ca/Douglas-Chicago-Hotels-Cheap-Hotels.0-n6132367-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Douglas](https://www.expedia.ca/Douglas-Chicago-Hotels-Hotel-With-Early-Check-In.0-n6132367-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Douglas](https://www.expedia.ca/Douglas-Chicago-Hotels-Hotels-With-Bar.0-n6132367-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Douglas Hotels](https://www.expedia.ca/Douglas-Chicago-Hotels.0-n6132367-0.Travel-Guide-Filter-Hotels) - [Business Hotels in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Business-Hotel.0-n6350699-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Couples-Resorts-Hotels.0-n6350699-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Golf-Hotel.0-n6350699-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Green Hotels in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Green-Sustainable.0-n6350699-0-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-A-Lazy-River.0-n6350699-0-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-Childcare.0-n6350699-0-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-Tennis-Courts.0-n6350699-0-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-Waterslides.0-n6350699-0-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Mountain-Hotels.0-n6350699-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Ski Hotels in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Ski-Hotel.0-n6350699-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Waterpark-Hotels.0-n6350699-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Winery-Hotel.0-n6350699-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Downtown Chicago Hotels](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Grand Boulevard](https://www.expedia.ca/Grand-Boulevard-Chicago-Hotels-Adults-Only-Resorts.0-n6132310-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Grand Boulevard Hotels](https://www.expedia.ca/Grand-Boulevard-Chicago-Hotels.0-n6132310-0.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Beach-Hotel.0-n117842-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Cheap-Hotels.0-n117842-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Historic-Hotel.0-n117842-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Spa-Hotel.0-n117842-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels near Hyde Park Hair Salon](https://www.expedia.ca/Hyde-Park-Hair-Salon-Hotels.0-l553248621533116334-0.Travel-Guide-Filter-Hotels) - [Hotels near Ida B Wells House](https://www.expedia.ca/Ida-B-Wells-House-Hotels.0-l553248621533116338-0.Travel-Guide-Filter-Hotels) - [Hotels near Illinois Institute of Technology](https://www.expedia.ca/Illinois-Institute-Of-Technology-Hotels.0-l6168375-0.Travel-Guide-Filter-Hotels) - [Vacation Homes in Indiana Station](https://www.expedia.ca/Indiana-Station-Private-Vacation-Homes.d6211032-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Cheap Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Cheap-Hotels.0-n6132343-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Luxury-Hotel.0-n6132343-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Spa-Hotel.0-n6132343-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Kenwood Hotels](https://www.expedia.ca/Kenwood-Chicago-Hotels.0-n6132343-0.Travel-Guide-Filter-Hotels) - [Lake Meadows Hotels](https://www.expedia.ca/Lake-Meadows-Chicago-Hotels.0-n553248635976478388-0.Travel-Guide-Filter-Hotels) - [Hotels near Lakefront Trail](https://www.expedia.ca/Lakefront-Trail-Hotels.0-l553248621561883133-0.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Couples-Resorts-Hotels.0-n800025-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Romantic-Hotel.0-n800025-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Waterpark-Hotels.0-n800025-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Winery-Hotel.0-n800025-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Hotels near McCormick Place](https://www.expedia.ca/McCormick-Place-Hotels.0-l6069191-0.Travel-Guide-Filter-Hotels) - [Hotels near McCormick Tribune Center](https://www.expedia.ca/McCormick-Tribune-Center-Hotels.0-l553248621555594739-0.Travel-Guide-Filter-Hotels) - [Condo Rentals in South Side](https://www.expedia.ca/South-Side-Condos.d553248635074842823-aaCondos.Travel-Guide-Accommodation) - [Adults Only Resorts & in South Side](https://www.expedia.ca/South-Side-Hotels-Adults-Only-Resorts.0-0-d553248635074842823-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Boutique Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-Boutique-Hotel.0-0-d553248635074842823-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Club Quarters Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-Club-Quarters.0-0-d553248635074842823--bClubQuarters.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in South Side](https://www.expedia.ca/South-Side-Hotels-Hotel-With-Early-Check-In.0-0-d553248635074842823-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in South Side](https://www.expedia.ca/South-Side-Hotels-Hotels-With-Free-Parking.0-0-d553248635074842823-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in South Side](https://www.expedia.ca/South-Side-Hotels-Hotels-With-Smoking-Rooms.0-0-d553248635074842823-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-LGBT-Friendly-Hotel.0-0-d553248635074842823-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Loews Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-Loews.0-0-d553248635074842823--bLoews.Travel-Guide-Filter-Hotels) - [Motel 6 Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-Motel-6.0-0-d553248635074842823--bMotel6.Travel-Guide-Filter-Hotels) - [Sonesta Hotel in South Side](https://www.expedia.ca/South-Side-Hotels-Sonesta-Hotel.0-0-d553248635074842823--bSonestaHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-Spa-Hotel.0-0-d553248635074842823-tSpaHotel.Travel-Guide-Filter-Hotels) - [South Side Hotels](https://www.expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels) - [Motels in South Side](https://www.expedia.ca/South-Side-Motels.d553248635074842823-aaMotels.Travel-Guide-Accommodation) - [Resorts in South Side](https://www.expedia.ca/South-Side-Resort-Hotels.d553248635074842823-aaResortHotels.Travel-Guide-Accommodation) - [Hotels with Early Check-in in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotel-With-Early-Check-In.0-n800024-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Washington Park Court Hotels](https://www.expedia.ca/Washington-Park-Court-Chicago-Hotels.0-n6132200-0.Travel-Guide-Filter-Hotels) - [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Visit Fuller Park](https://www.expedia.ca/Chicago-Fuller-Park.dx6132374) - [Visit Indian Village](https://www.expedia.ca/Chicago-Indian-Village.dx553248635976382922) - [Chicago Vacations](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides) - [Obama's House](https://www.expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction) - [Visit South Side](https://www.expedia.ca/South-Side.dx553248635074842823) - [Book Hotels in Oakland on Expedia.com](https://www.expedia.com/Oakland-Chicago-Hotels-Luxury-Hotel.0-n6132392-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)