Title: Book the Best South Side CASINO Hotels & Resorts in 2026 | 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) ![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Casino Hotels in South Side, IL from CA $105 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 Casino Hotels Tonight [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-28&endDate=2025-12-29&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-29&endDate=2025-12-30&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-09&endDate=2026-01-11&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side hotels with a casino ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1349h899x0y1-6bfcf9ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/46e46203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-3830b9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-166f73c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6 [](https://www.expedia.ca/Chicago-Hotels-Sunflower-Apt-12-Min-From-Downtown-CHI.h91086437.Hotel-Information) Brighton Park 8.6/10 Excellent (20) "Clean and nice. My son loved the arcade game. Would stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nichole S. CA $115 CA $312 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Chicago-Hotels-Sunflower-Apt-12-Min-From-Downtown-CHI.h91086437.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/279c3768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d2b26aad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/9097f753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Felix River North/Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) Downtown Chicago 8.2/10 Very good (2481) "Decent hotel in a great location with extremely helpful staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/6000000/5510000/5502000/5501975/290e657b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/6000000/5510000/5502000/5501975/4769bf4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/6000000/5510000/5502000/5501975/eeb37134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5510000/5502000/5501975/1862036f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Chicago/River North [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-ChicagoRiver-North.h5501975.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1616) "Really enjoy the location and the breakfast was the best! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly CA $154 CA $181 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-ChicagoRiver-North.h5501975.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22300/22287/33fa163a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22300/22287/3e153ec3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22300/22287/437499f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22300/22287/d7c6e720.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Chicago - Magnificent Mile by IHG [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Chicago-Magnificent-Mile.h22287.Hotel-Information) Downtown Chicago 8.4/10 Very good (1004) "Clean, accesible to nearby establishments and staff were so polite and helpful to our needs." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose Darwin CA $108 CA $127 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Chicago-Magnificent-Mile.h22287.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/26800/26728/43618bdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/26800/26728/w4000h2663x0y0-e77bab8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26800/26728/46dc6ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Corner](https://images.trvl-media.com/lodging/1000000/30000/26800/26728/w4000h2662x0y0-2cdbdb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel 55 [](https://www.expedia.ca/Chicago-Hotels-Hotel-55.h26728.Hotel-Information) Downtown Chicago 8.8/10 Excellent (1552) "Staff was amazing, rooms were great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brigit CA $162 CA $230 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Chicago-Hotels-Hotel-55.h26728.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/f3b451c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/ca3aaed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, pizza](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/27ecd933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/f9eb35b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Chicago O'Hare Airport [](https://www.expedia.ca/Chicago-Hotels-Comfort-Suites-Schiller-Park-Chicago-OHare-Airport.h664918.Hotel-Information) Schiller Park 8.0/10 Very good (2762) "The room was clean, the staff who checked me in was kind and fast. Loved my stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosette CA $92 CA $105 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Chicago-Hotels-Comfort-Suites-Schiller-Park-Chicago-OHare-Airport.h664918.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1090000/1085800/1085742/w3840h2556x0y4-5ff73d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1090000/1085800/1085742/a4d0c663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1090000/1085800/1085742/88547dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1090000/1085800/1085742/00a39f53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Munster [](https://www.expedia.ca/Munster-Hotels-Hampton-Inn-And-Suites-Munster.h1085742.Hotel-Information) Munster 8.6/10 Excellent (1001) "Friendly staff, nice and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shauntel CA $116 CA $130 total includes taxes & fees Jan 24 - Jan 25, 2026 [](https://www.expedia.ca/Munster-Hotels-Hampton-Inn-And-Suites-Munster.h1085742.Hotel-Information) ![Casino](https://images.trvl-media.com/lodging/113000000/112060000/112051600/112051593/36337dd5.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) ![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) ### Wind Creek Southland Casino and Hotel [](https://www.expedia.ca/Chicago-Hotels-Wind-Creek-Southland-Casino-And-Hotel.h112051593.Hotel-Information) East Hazel Crest 9.4/10 Exceptional (214) "Nice size rooms, staff was polite and very helpful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) WILLIAM CA $211 CA $237 total includes taxes & fees Jan 28 - Jan 29, 2026 [](https://www.expedia.ca/Chicago-Hotels-Wind-Creek-Southland-Casino-And-Hotel.h112051593.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409441/0c27864d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409441/e079772d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409441/9e5a61fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409441/7f282932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New 4 King Bed / Family Ready Apartment [](https://www.expedia.ca/Chicago-Hotels-Brand-New-4BR-In-Heart-Of-Chicago.h118409441.Hotel-Information) Near North Side 10/10 Exceptional (5) "We had a fantastic stay at this VRBO apartment! The check-in process was smooth and hassle-free, and the host maintained excellent communication throughout our visit. The apartment itself was well maintained and part of a wonderful complex that felt both welcoming and peaceful. The neighborhood felt very safe. We especially loved that we could easily walk to nearby restaurants, coffee shops, and shopping. Everything we needed was just a short stroll away. Highly recommend for anyone looking for... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaci T. CA $319 CA $785 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Chicago-Hotels-Brand-New-4BR-In-Heart-Of-Chicago.h118409441.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/6402f922.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/3fb360e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/e7e820fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago O'Hare Airport [](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information) O'Hare 8.2/10 Very good (2176) "Early check in available for $25, worth it for getting rest between flights. Very friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $268 CA $315 total includes taxes & fees Jan 17 - Jan 18, 2026 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.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=2026-01-11&endDate=2026-01-12®ionId=553248635074842823&adults=2&amenities=CASINO&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Staff was friendly and very helpful. Hotel was really clean" [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.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) - [B&B in Chicago 47th Street Station ](https://www.expedia.ca/Chicago-47th-Street-Station-Bed-And-Breakfast.d6212783-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Chicago 47th Street Station ](https://www.expedia.ca/Chicago-47th-Street-Station-Hotels.d6212783.Travel-Guide-Hotels) - [Guest Houses in Chicago 51st-53rd Street Station ](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Guest-Houses.d6212787-aaGuestHouses.Travel-Guide-Accommodation) - 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