Title: Book the Best South Side Hotels with smoking rooms 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 Smoking 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 Hotels with smoking rooms Tonight [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-03&endDate=2025-10-05&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) ## Top South Side Hotels with smoking rooms ![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) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a9c979ca.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 (2163) "Great hotel " CA $267 CA $354 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Couples treatment rooms, sauna, body treatments, aromatherapy](https://images.trvl-media.com/lodging/113000000/112060000/112051600/112051593/1fba48a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, body treatments, aromatherapy](https://images.trvl-media.com/lodging/113000000/112060000/112051600/112051593/6dc765e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/113000000/112060000/112051600/112051593/d54345c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, body treatments, aromatherapy](https://images.trvl-media.com/lodging/113000000/112060000/112051600/112051593/711c3d4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wind Creek Southland Casino and Hotel East Hazel Crest 9.4/10 Exceptional (131) "Amazing hotel " CA $250 CA $280 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chicago-Hotels-Wind-Creek-Southland-Casino-And-Hotel.h112051593.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.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/1000000/20000/18600/18514/172457c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/d24507d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago/Magnificent Mile Suites Downtown Chicago 8.8/10 Excellent (3010) "Enjoyed our stay" CA $205 CA $241 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/b66dd193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, towels](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/026f1c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/ea25cb66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/b1d231c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Admiral Motel By Oyo Chicago I-94 Chatham 4.0/10 (32) "It was a great hotel" CA $78 CA $103 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/84aefbd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/6c3662e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-refrigerator](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/b118c2d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/3da50eb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Skylark Motel Garfield Ridge 4.6/10 (118) "Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal." CA $150 CA $177 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/62703e26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, towels](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/130fbf4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/10d8c32c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/d6e23b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capital O Empire Motel Chicago I-94 Greater Grand Crossing 3.8/10 (18) "I would feel safer sleeping on the street than this motel. " CA $81 CA $105 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Empire-Motel.h118831367.Hotel-Information) ![Hallway](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/19cdbb10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/f16d7e14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/7076eeb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/30d5c7e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Motel By OYO Chicago I-90 Woodlawn 3.4/10 (45) "Easy, safe parking " CA $78 CA $106 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/101000000/100810000/100803500/100803423/f4f30336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi](https://images.trvl-media.com/lodging/101000000/100810000/100803500/100803423/b5d042e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100810000/100803500/100803423/52c486f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/101000000/100810000/100803500/100803423/a0b2fefb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru By Hilton Merrillville Merrillville 9.2/10 Wonderful (324) "Wonderful place to stay!" CA $141 CA $158 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Merrillville-Hotels-Tru-By-Hilton-Merrillville.h100803423.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/bc751856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, minibar](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/0347f2d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/30794842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago 9.2/10 Wonderful (298) "Had a great uneventful stay" CA $299 CA $351 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Grand-Vacations-Chicago-Downtown-Magnificent-Mile.h37641670.Hotel-Information) ![Executive lounge](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Steam room, body treatments, facials, 2 treatment rooms, massages](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/037db98f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/84fcc5bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Steam room, body treatments, facials, 2 treatment rooms, massages](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/b376d4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Chicago at Millennium Park Downtown Chicago 8.6/10 Excellent (1971) "Perfect location, very clean, super comfy bed + pillows! Would stay there again! " CA $355 CA $458 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.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=2025-10-17&endDate=2025-10-18®ionId=553248635074842823&adults=2&property_amenities_group_explore=designated_smoking_areas&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Carlton Inn Midway](//images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "C L E A N" [](https://expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.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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