Title: Book the Best BUSINESS Hotels in South Side 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 Business Hotels 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 Business Hotels Tonight [Sep 22 - Sep 23](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-09-22&endDate=2025-09-23&adults=2&travelerType=BUSINESS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 23 - Sep 24](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-09-23&endDate=2025-09-24&adults=2&travelerType=BUSINESS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-09-26&endDate=2025-09-28&adults=2&travelerType=BUSINESS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-03&endDate=2025-10-05&adults=2&travelerType=BUSINESS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Business Hotels ## Our top choices for South Side business-friendly hotels ![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/af0ef9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/c12c78f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/0ec157ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/w3576h2561x0y0-5f9110d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric The Loop Chicago Downtown Chicago 9.0/10 Wonderful (2145) "Great place and really nice people " CA $308 CA $361 total includes taxes & fees Sep 26 - Sep 27 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 King Bed (Loft Suite)](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/397918af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 King Bed (Loft Suite)](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/0b950ebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Emily Hotel Downtown Chicago 9.2/10 Wonderful (1228) "The hotel is beautiful! Great staff and perfect location" CA $291 CA $341 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chicago-Hotels-Ace-Hotel-Chicago.h19381112.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/5ea33759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/7744cb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/bab7a943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/2d37be79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Claridge House Downtown Chicago 9.0/10 Wonderful (1377) "We had a great stay" CA $167 CA $236 total includes taxes & fees Sep 24 - Sep 25 [](https://www.expedia.ca/Chicago-Hotels-Claridge-House.h22684.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/ffbe5574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/8f681739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/b456698d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sophy Hyde Park Hyde Park 9.6/10 Exceptional (1008) "Loved my stay!" CA $371 CA $473 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/e1b9cc64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/2f40f114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking | Living area](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/4e3574c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Chicago Chinatown Chinatown 9.6/10 Exceptional (1008) "The breakfast was delicious and the parking was very convenient!!" CA $274 CA $322 total includes taxes & fees Sep 23 - Sep 24 [](https://www.expedia.ca/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/3dbc8b3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/f80081f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/98e3ca35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG Bedford Park 9.0/10 Wonderful (1141) "Loved the proximity, and airport shuttle, to the airport. The staff was friendly, breakfast perfect, and the bed comfortable." CA $199 CA $233 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/517a0e3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 11 per person)](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/4c3ef871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/30dbed81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Chicago-South/University Medical Center Hyde Park 8.8/10 Excellent (1006) "The folks were very kind and the location was excellent " CA $274 CA $322 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.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) ![Buffet breakfast on weekends (USD 26.00 per person)](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/04630218.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 (886) "Great place" CA $211 CA $248 total includes taxes & fees Sep 26 - Sep 27 [](https://www.expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/f5aef82f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/87403ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/09cd06f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Inn & Suites - Midway Airport Burbank 6.6/10 (1003) "Pleasant stuff, comfy bed, would stay again." CA $169 CA $187 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/c4821ce0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/w1080h1353x0y0-3dea97aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/w1080h1440x0y8-2e6765a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/74d36cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax & Unwind in This Comfortable 3BR Unit Calumet Park 10/10 Exceptional (4) "Lakeia was very accommodating throughout our stay." CA $190 CA $430 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Chicago-Hotels-Cozy-3BR-Getaway-W-Bonus-Loft-Parking-South-Suburbs-Chicago.h116238230.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=2025-10-06&endDate=2025-10-07®ionId=553248635074842823&adults=2&travelerType=business_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](//images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17_y.jpg) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG 10/10 Excellent "perfect location for a flight out. It was clean and staff very helpful with directions to game." [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![Jaslin Hotel](//images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "The hotel was very nice. The room was very clean. the staff was very friendly. However, the exercise facility needs a major upgrade. There is a gross lack of quality equipment. In short, the gym needs a full assessment and a total makeover. Other than the gym, the Jaslin Hotel is a great place to stay. " [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Chicago Marriott Midway](//images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "Quie" [](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Carlton Inn Midway](//images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "Convenient " [](https://expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ![Hyatt Place Chicago-South/University Medical Center](//images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "Loved it" [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chinatown Hotel Chicago](//images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "I felt very comfortable" [](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![Best Western Inn & Suites - Midway Airport](//images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg) ### Best Western Inn & Suites - Midway Airport 10/10 Excellent "Pleasant stuff, comfy bed, would stay again." 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[Hotels near Garfield Station](https://www.expedia.ca/Garfield-Station-Hotels.d6210926.Travel-Guide-Hotels) - [Inns in Garfield Station](https://www.expedia.ca/Garfield-Station-Inns.d6210926-aaInns.Travel-Guide-Accommodation) - [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) - [All Inclusive Resorts and in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-All-Inclusive-Hotel.0-n117842-0-tAllInclusiveHotel.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) - [Boutique Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Boutique-Hotel.0-n117842-0-tBoutiqueHotel.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) - 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[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) - [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) - 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[Visit Indian Village](https://www.expedia.ca/Chicago-Indian-Village.dx553248635976382922) - [Chicago Museum of Science and Industry](https://www.expedia.ca/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction) - [Obama's House](https://www.expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction) - [Robie House](https://www.expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction) - [Car rentals near Hyde Park](https://www.expedia.ca/Car-Rentals-In-Hyde-Park.d117842.Car-Rental-Guide) - [Hertz Rental Cars in Hyde Park](https://www.expedia.ca/Hertz-Car-Rentals-In-Hyde-Park.d117842-c40.Car-Rental-Guide-Suppliers) - [Book Business Hotels in South Side on Expedia.com](https://www.expedia.com/South-Side-Hotels-Business-Hotel.0-0-d553248635074842823-tBusinessHotel.Travel-Guide-Filter-Hotels)