Title: TOP Smoking Hotels in South Side, IL for 2025 | 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, IL featuring interior views and an airport as well as a couple](https://images.trvl-media.com/place/5719117/eadab43c-a88e-4198-bdcd-703715c2ebbd.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by by Midway Intl Airport # 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 [5 Nov - 6 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [6 Nov - 7 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-11-06&endDate=2025-11-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [7 Nov - 9 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [14 Nov - 16 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Hotels with smoking rooms ![Room, 1 King Bed, Smoking | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3456h2297x0y3-13e176b4.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, Smoking (Jetted Tub) | Bathroom | Free toiletries, towels](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/ad19fb9f.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) ### Saratoga Motel By Capital O Near Midway Airport Chicago IL Ashburn 5.4/10 (10) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Albert £64 includes taxes & fees 6 Nov - 7 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.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) ![Interior](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/w1080h1440x0y16-cbb4ff2e.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) ### Relax & Unwind in This Comfortable 3BR Unit Calumet Park 10/10 Exceptional (5) "We just stayed one night on our way to another destination. The home was very clean and well presented when we arrived. We had no issues and would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ebony J. £256 includes taxes & fees 12 Nov - 13 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-3BR-Getaway-W-Bonus-Loft-Parking-South-Suburbs-Chicago.h116238230.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) ![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) ![Mini fridge](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/b118c2d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Skylark Motel Garfield Ridge 4.6/10 (119) "The proximity to Midway was great. Other than that, it was pretty bad, holes in the floor, scarry shower. However, I didn't have to sleep on the floor at the airport, so I guess there is that." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian £75 includes taxes & fees 6 Nov - 7 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Skylark-Motel.h1658428.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 | 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) ![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 Chatham 4.0/10 (38) "Fine stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharmaine £56 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.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) ![Room, 1 King Bed, Smoking | 1 bedroom, 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) ### Best Motel By OYO Chicago I-90 Woodlawn 3.4/10 (47) "Easy, safe parking " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ramon £74 includes taxes & fees 6 Nov - 7 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/ae5791b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bed sheets](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/093eee5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/62703e26.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) ### Capital O Empire Motel Chicago I-94 Greater Grand Crossing 3.4/10 (22) "False advertisement: they are no longer associated with OYO so the use of the "Capital O" name is misleading. Under new ownership of arabs and Africans and it looks like it. Holes in the walls from maintenece AND mice, no wifi, homeless folks sleeping in and around the place, maintenace leaves trash in the center of the parking lot for the hobos to rummage through. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Savon £58 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Empire-Motel.h118831367.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) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/2866aa1e.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) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago 9.4/10 Exceptional (2249) "Room was spotless…staff was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tamika £120 includes taxes & fees 25 Nov - 26 Nov [](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) ![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, 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) ### Hilton Chicago/Magnificent Mile Suites Downtown Chicago 9.0/10 Wonderful (3233) "Overall it was a great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward £91 includes taxes & fees 17 Nov - 18 Nov [](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) ![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) ![Premium bedding, down duvets, pillow-top beds, minibar](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/2e9bef56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Chicago at Millennium Park Downtown Chicago 8.6/10 Excellent (1997) "Beautiful property and room was very comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paula £184 includes taxes & fees 23 Nov - 24 Nov [](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) ![Fitness facility](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102878/f1823194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102878/w3839h2564x0y3-1cb33116.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 Downtown Chicago 9.4/10 Exceptional (1421) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George £118 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Canopy-By-Hilton-Chicago-Central-Loop.h68102878.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=2025-11-19&endDate=2025-11-20®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 "Very friendly! With airport shuttle!" 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[The Peninsula Group Hotels in Hyde Park](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-The-Peninsula-Group.0-n117842-0--bThePeninsulaGroup.Travel-Guide-Filter-Hotels) - [Hyde Park Hotels](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels.0-n117842-0.Travel-Guide-Filter-Hotels) - [Indian Village Hotels](https://www.expedia.co.uk/Indian-Village-Chicago-Hotels.0-n553248635976382922-0.Travel-Guide-Filter-Hotels) - [Destination Hotels in Kenwood](https://www.expedia.co.uk/Kenwood-Chicago-Hotels-Destination-Hotels.0-n6132343-0--bDestinationHotels.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Kenwood](https://www.expedia.co.uk/Kenwood-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132343-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Kenwood Hotels](https://www.expedia.co.uk/Kenwood-Chicago-Hotels.0-n6132343-0.Travel-Guide-Filter-Hotels) - [Hotels near Lake Meadows Park](https://www.expedia.co.uk/Lake-Meadows-Park-Hotels.0-l6132351-0.Travel-Guide-Filter-Hotels) - [Hotels near McCormick Place](https://www.expedia.co.uk/McCormick-Place-Hotels.0-l6069191-0.Travel-Guide-Filter-Hotels) - [Mckinley Park Hotels](https://www.expedia.co.uk/McKinley-Park-Chicago-Hotels.0-n6132389-0.Travel-Guide-Filter-Hotels) - [Casino Hotels in Near South Side](https://www.expedia.co.uk/Near-South-Side-Chicago-Hotels-Casino-Hotel.0-n6132399-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Near South Side Hotels](https://www.expedia.co.uk/Near-South-Side-Chicago-Hotels.0-n6132399-0.Travel-Guide-Filter-Hotels) - [Oakland Hotels](https://www.expedia.co.uk/Oakland-Chicago-Hotels.0-n6132392-0.Travel-Guide-Filter-Hotels) - [Hotels near Robert W Roloson Houses](https://www.expedia.co.uk/Robert-W-Roloson-Houses-Hotels.0-l553248621533116343-0.Travel-Guide-Filter-Hotels) - [Hotels near SR Crown Hall](https://www.expedia.co.uk/SR-Crown-Hall-Hotels.0-l553248621533116346-0.Travel-Guide-Filter-Hotels) - [Hotels near Soldier Field](https://www.expedia.co.uk/Soldier-Field-Hotels.0-l6058043-0.Travel-Guide-Filter-Hotels) - [South Loop Hotels](https://www.expedia.co.uk/South-Loop-Chicago-Hotels.0-n6130108-0.Travel-Guide-Filter-Hotels) - [South Shore Hotels](https://www.expedia.co.uk/South-Shore-Chicago-Hotels.0-n6132437-0.Travel-Guide-Filter-Hotels) - [Apartments in Southwest Side](https://www.expedia.co.uk/Southwest-Side-Apartments.d553248635976475403-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Southwest Side](https://www.expedia.co.uk/Southwest-Side-Cabins.d553248635976475403-aaCabins.Travel-Guide-Accommodation) - [Hotels near University of Chicago](https://www.expedia.co.uk/University-Of-Chicago-Hotels.0-l6064081-0.Travel-Guide-Filter-Hotels) - [Washington Park Hotels](https://www.expedia.co.uk/Washington-Park-Chicago-Hotels.0-n171466-0.Travel-Guide-Filter-Hotels) - [West Englewood Hotels](https://www.expedia.co.uk/West-Englewood-Chicago-Hotels.0-n6132412-0.Travel-Guide-Filter-Hotels) - [Hotels near Wintrust Arena](https://www.expedia.co.uk/Wintrust-Arena-Hotels.0-l553248634328853320-0.Travel-Guide-Filter-Hotels) - [Flights to Chicago](https://www.expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights to Southwest Side](https://www.expedia.co.uk/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights) - [Visit Grand Boulevard](https://www.expedia.co.uk/Chicago-Grand-Boulevard.dx6132310) - [Visit Hyde Park](https://www.expedia.co.uk/Chicago-Hyde-Park.dx117842) - [Visit Jackson Park Highlands](https://www.expedia.co.uk/Chicago-Jackson-Park-Highlands.dx6132329) - [Visit Near South Side](https://www.expedia.co.uk/Chicago-Near-South-Side.dx6132399) - [Visit Prairie District](https://www.expedia.co.uk/Chicago-Prairie-District.dx553248635976473159) - [Visit South Commons](https://www.expedia.co.uk/Chicago-South-Commons.dx6132263) - [Visit South Loop](https://www.expedia.co.uk/Chicago-South-Loop.dx6130108) - [Chicago Holidays](https://www.expedia.co.uk/Chicago.d178248.Holidays-City-Breaks) - [Essex Holidays](https://www.expedia.co.uk/Essex.d6132371.Holidays-City-Breaks) - [Hyde Park Holidays](https://www.expedia.co.uk/Hyde-Park.d117842.Holidays-City-Breaks) - [Robie House](https://www.expedia.co.uk/Robie-House-Hyde-Park.d6064059.Attraction) - [Sr Crown Hall](https://www.expedia.co.uk/SR-Crown-Hall-Bronzeville.d553248621533116346.Attraction) - [S.s. Peter and Paul Church](https://www.expedia.co.uk/SS-Peter-And-Paul-Church-McKinley-Park.d6247219.Attraction) - [Car hire near Lake Meadows Park](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lake-Meadows-Park.d6132351.Car-Hire-Guide) - [Enterprise Rental Cars in Hyde Park](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Hyde-Park.d117842-c15.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in Southwest Side](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Southwest-Side.d553248635976475403-c15.Car-Rental-Guide-Suppliers) - [Europcar Rental Cars in Hyde Park](https://www.expedia.co.uk/Europcar-Car-Rentals-In-Hyde-Park.d117842-c14.Car-Rental-Guide-Suppliers) - [Book Hotels with smoking rooms in South Side on Expedia.com](https://www.expedia.com/South-Side-Hotels-Hotels-With-Smoking-Rooms.0-0-d553248635074842823-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels)