Title: TOP Smoking Hotels in South Side, IL for 2026 | Expedia.co.uk [South Side Travel Guide](https://expedia.co.uk/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.co.uk/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Holiday Rentals in South Side](https://expedia.co.uk/South-Side-Holiday-Rentals.d553248635074842823.Travel-Guide-HolidayRentals)[Flights to South Side](https://expedia.co.uk/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.co.uk/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-South-Side.d553248635074842823.Car-Hire-Guide)[South Side Holidays](https://expedia.co.uk/South-Side.d553248635074842823.Holidays-City-Breaks) ![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [12 Feb - 13 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-02-12&endDate=2026-02-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [13 Feb - 14 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-02-13&endDate=2026-02-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [13 Feb - 15 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side hotels with designated smoking areas ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3456h2300x0y0-6e038619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self-parking](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/ed8b3d68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3451h2304x0y0-39d39828.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking (Jetted Tub) | Jetted bathtub](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3448h2304x4y0-e45070c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Saratoga Motel By Capital O Near Midway Airport Chicago IL [](https://www.expedia.co.uk/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.Hotel-Information) Ashburn 7.0/10 Good (32 reviews) "Great hosts" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John £55 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.Hotel-Information) ![Free WiFi](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/a2a4ef31.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/38fe6f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/953521af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Skylark Motel [](https://www.expedia.co.uk/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information) Garfield Ridge 4.6/10 (119 reviews) "Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen £74 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/919fb8df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self-parking, free valet parking](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/208b55cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/1cf69111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/275d47ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Motel By OYO Chicago I-90 [](https://www.expedia.co.uk/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.Hotel-Information) Woodlawn 3.6/10 (52 reviews) "Room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nyi £68 includes taxes & fees 13 Feb - 14 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/cdb6bc21.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 | Desk, bed sheets](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/ea25cb66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/b66dd193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Admiral Motel By Oyo Chicago I-94 [](https://www.expedia.co.uk/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information) Chatham 3.8/10 (46 reviews) "Fine stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharmaine £65 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/833194a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a419e8db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago/Magnificent Mile Suites [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (3,790 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer £77 includes taxes & fees 19 Feb - 20 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillow-top beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a68260d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/444bc42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Latin American cuisine ](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/cadeb422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton [](https://www.expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (2,365 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Blake £130 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.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) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7e178380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down duvets, pillow-top beds, minibar](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7915e59f.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) ### Fairmont Chicago at Millennium Park [](https://www.expedia.co.uk/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2,063 reviews) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kamilah £172 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102878/w3837h2621x0y0-a6e97c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102878/7cc481f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102878/f2864387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed (Peloton Wellness Room) | In-room safe, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102878/8582f8bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canopy by Hilton Chicago Central Loop [](https://www.expedia.co.uk/Chicago-Hotels-Canopy-By-Hilton-Chicago-Central-Loop.h68102878.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,477 reviews) "Great place to stay…near to many nice places to visit." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jorge £119 includes taxes & fees 20 Feb - 21 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Canopy-By-Hilton-Chicago-Central-Loop.h68102878.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/bc751856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Premium bedding, pillow-top beds, minibar, in-room safe](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/0347f2d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/7f6bfac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Grand Vacations Club Chicago Magnificent Mile [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Grand-Vacations-Chicago-Downtown-Magnificent-Mile.h37641670.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (347 reviews) "Service was amazing and the location was perfect. Would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley Nicole £143 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Grand-Vacations-Chicago-Downtown-Magnificent-Mile.h37641670.Hotel-Information) ![Couples treatment room(s), 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 room(s), 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) ![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 room(s), 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) ### Wind Creek Southland Casino and Hotel [](https://www.expedia.co.uk/Chicago-Hotels-Wind-Creek-Southland-Casino-And-Hotel.h112051593.Hotel-Information) East Hazel Crest 9.2/10 Wonderful (253 reviews) "Staff was very nice and room was clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Monique £125 includes taxes & fees 19 Feb - 20 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Wind-Creek-Southland-Casino-And-Hotel.h112051593.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.co.uk/Hotel-Search?startDate=2026-02-26&endDate=2026-02-27®ionId=553248635074842823&adults=2&property_amenities_group_explore=designated_smoking_areas&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AFFINITY_SPRING_PROMO_553248635074842823) ## Top South Side Hotel Reviews ![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "It is a good place to stay." 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