Title: Book the Best South Side Hotels with Early Check-in in 2025 | Expedia.ca [South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26577-Museum-Of-Science-And-Industry.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Early Check-in in South Side, IL ![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 South Side Hotels with Early Check-in Tonight [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-05&endDate=2025-10-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-06&endDate=2025-10-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Hotels with Early Check-in ![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) ![Interior detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/c14e1876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freehand Chicago Downtown Chicago 8.0/10 Very good (2417) "Great walkable location to all the sights! " CA $113 CA $158 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/eac67ea5.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/1000000/20000/15100/15087/2c655ed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/ac302b90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/f00e51d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Millennium Knickerbocker Chicago Downtown Chicago 8.6/10 Excellent (1974) "We have stayed here several times and love the hotel and location." CA $128 CA $183 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/c3e40006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room | Courtyard view](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/5ad45e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/b910c9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/acaa7b12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Carleton of Oak Park Oak Park 9.0/10 Wonderful (1002) " the facility was excellent ...........hope to stay there in the future!" CA $171 CA $190 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Chicago-Hotels-Carleton-Of-Oak-Park.h9186.Hotel-Information) ![Living room](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/e921e6b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/273b53b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d0c2eca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chic 3 BR CONDO](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d323a9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dubois Guest House Bronzeville 8.4/10 Very good (71) "Very convenient for a short term stay with private area and clean shared spaces the parking is very convenient as well" CA $92 CA $158 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/a475d71a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/67f6b752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/7e84f30b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Marriott Midway Bedford Park 8.4/10 Very good (895) "Very clean and friendly staff" CA $180 CA $211 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/a9b3121a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ecc0a878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/eacd6d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 Queen Bed (Studio Apartment) | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/1bf06d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sentral Michigan Avenue Downtown Chicago 9.2/10 Wonderful (949) "Great location and cleanliness of rooms. Staff was extremely helpful " CA $212 CA $290 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information) ![American cuisine](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/c46ad167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/871940a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![American cuisine](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/fb80c7da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Plaza Chicago West Loop by IHG Downtown Chicago 9.0/10 Wonderful (1576) "Hotel was very comfortable and I felt very safe during my entire stay. " CA $211 CA $247 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/01c93cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel Downtown Chicago 8.4/10 Very good (1998) "Great property with great staff and amenities. " CA $242 CA $319 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.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/c5cac7c3.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/1000000/120000/116700/116674/04b62050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silversmith Hotel Chicago Downtown Downtown Chicago 9.4/10 Exceptional (1996) "Excellent hotel, staff, location. " CA $180 CA $253 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information) ![Room, Multiple Beds (The Drake Residence) | Living area](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/w3840h2550x0y3-037e0eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/7715e6da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/e945085d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Multiple Beds (The Drake Residence) | Living area](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/w3840h2549x0y4-79cac6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Drake Downtown Chicago 8.8/10 Excellent (1304) "Great historic hotel " CA $283 CA $332 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-The-Drake.h15092.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=2025-10-19&endDate=2025-10-20®ionId=553248635074842823&adults=2&property_amenities_group_explore=express_checkin&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Chinatown Hotel Chicago](//images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "Lots of affordable parking in the area and right by the red line" [](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [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) - [Luxury Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Luxury-Hotel.0-n6132245-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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