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) # Search Hotels with smoking rooms in South Side - ![](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 [26 Dec - 27 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-26&endDate=2025-12-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [27 Dec - 28 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [26 Dec - 28 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [2 Jan - 4 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side hotels with designated smoking areas ![Reception](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3451h2304x0y0-39d39828.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/c0b4d771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/c80663a4.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 7.2/10 Good (30) "Great hosts" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John £76 includes taxes & fees 28 Dec - 29 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.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) ![Free WiFi](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/3da50eb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini fridge](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/b118c2d6.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) ### Skylark Motel [](https://www.expedia.co.uk/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information) Garfield Ridge 4.6/10 (119) "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 £75 includes taxes & fees 19 Jan - 20 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Skylark-Motel.h1658428.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) ![Room, 1 King Bed, Smoking | Desk, bed sheets](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/eaa24bbf.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) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/7076eeb1.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 3.4/10 (48) "Clean room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pierre £80 includes taxes & fees 2 Jan - 3 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.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) ![Property entrance](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/b1d231c1.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) ![Exterior](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/d4687c67.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 (45) "Fine stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharmaine £71 includes taxes & fees 12 Jan - 13 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.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) ![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.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/a9c979ca.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) ### 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 (2277) "Great staff and restaurants!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abigale £101 includes taxes & fees 20 Jan - 21 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/0030a761.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/1000000/20000/18600/18514/172457c3.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) ### 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 (3577) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) RaShawna £78 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![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) ![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) ![Executive lounge](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/798cdd6a.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 (2031) "Great stay ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd £169 includes taxes & fees 29 Dec - 30 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/44167e80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/27e8c783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/w1320h783x0y1-af1e2329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Duplex, City View | Shared kitchen | Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/14e4f60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago luxury home suites [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information) Downtown Chicago 8.4/10 Very good (5) "Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Alex £92 includes taxes & fees 29 Dec - 30 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.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) ![Fitness facility](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102878/f1823194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102878/a94f90c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast (USD 21.00 per person)](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102878/5316f685.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 (1448) "Excellent location. The hotel is exceptional clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) meixin £113 includes taxes & fees 2 Jan - 3 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Canopy-By-Hilton-Chicago-Central-Loop.h68102878.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) ![Seasonal outdoor pool, pool loungers](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/949e3d56.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) ![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) ### 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 (332) "Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ursula £140 includes taxes & fees 7 Jan - 8 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Grand-Vacations-Chicago-Downtown-Magnificent-Mile.h37641670.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=2026-01-10&endDate=2026-01-11®ionId=553248635074842823&adults=2&property_amenities_group_explore=designated_smoking_areas&sort=RECOMMENDED&openPlayBack=true) ## 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 "Staff is great, clean rooms " [](https://expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - More ways to book - [4 Star Hotels in McKinley Park ](https://www.expedia.co.uk/4Star-McKinley-Park-Chicago-Hotels.s40-n6132389-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in New City ](https://www.expedia.co.uk/5Star-New-City-Chicago-Hotels.s50-n6132388-0.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Armour Square ](https://www.expedia.co.uk/Armour-Square-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132365-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - 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