Title: Book the Best LAKESIDE Hotels in South Side 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 Lake Hotels in South Side, IL - ![](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 Lake Hotels Tonight [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Lake Hotels ![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, 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) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/2866aa1e.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) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago 9.4/10 Exceptional (2232) "Great hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gilles CA $139 CA $211 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/c042bdff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/e47956bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6d9bcb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade Downtown Chicago 8.4/10 Very good (1406) "Beautiful hotel in a beautiful location. Would 100% stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ariana CA $156 CA $183 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Room, Multiple Beds (The Drake Residence) | Living area](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/w3840h2550x0y3-037e0eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/bdaa578c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Multiple Beds (The Drake Residence) | Living area](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/w3840h2549x0y4-79cac6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/e945085d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Drake Downtown Chicago 8.8/10 Excellent (1323) "Great historic hotel " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Tammie CA $188 CA $221 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Chicago-Hotels-The-Drake.h15092.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/c47ab94b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/5001f31e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/9baa79de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waldorf Astoria Chicago Downtown Chicago 9.4/10 Exceptional (1001) "This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) william CA $661 CA $775 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/429a2c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/6d229925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/1b553373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/eb6189bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ameristar Casino Hotel East Chicago East Chicago 8.6/10 Excellent (1003) "Nice rooms with food options on site. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $196 CA $234 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49500/49450/13282144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49500/49450/00a56fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49500/49450/b928c10a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49500/49450/2f6ff477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Lodge Oak Brook Chicago Oak Brook 8.8/10 Excellent (1009) "Love the architectural design of the Hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen Ann CA $202 CA $220 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Lodge.h49450.Hotel-Information) ![City view](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/df55aaa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/d8be0ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Asian cuisine](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/947219c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency McCormick Place Chicago Near South Side 9.0/10 Wonderful (1031) "Great location, friendly staff, clean spacious room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose CA $251 CA $327 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1350h899x0y1-d7005b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1349h899x1y1-7309c990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/1dd62bdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, offices](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1350h899x0y1-19b66913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Boho Chicago - 10 Minutes to Downtown Chicago Little Village 10/10 Exceptional (8) "Seriously, very beautiful place to stay like the title of the announce. Cozy and affordable!! I highly recommend if you plan to visit Chicago for a week!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Christian M. CA $87 CA $288 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-Cozy-Boho-Chicago-10-Min-To-Chicago.h105552490.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103080000/103078200/103078175/94320961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103080000/103078200/103078175/3360f72d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103080000/103078200/103078175/eff21aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/104000000/103080000/103078200/103078175/38f3dd97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake Uptown 9.8/10 Exceptional (11) "The soundproofing and cleanliness could have been better, but the host always did their best to fix any issues. Really appreciate their effort, and I’d definitely recommend staying with them!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) WOOJIN K. CA $76 CA $310 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Chicago-Hotels-Peaceful-Beachfront-Loft-Free-Parking-Rooftop-Gym.h103078175.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103570000/103560800/103560718/edc4c7ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/104000000/103570000/103560800/103560718/f03dce7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103570000/103560800/103560718/4a8e04d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103570000/103560800/103560718/f53004fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Majestic Modern Style|13 mins DT|4 mins Lake Uptown 9.4/10 Exceptional (11) "Wonderful property, fabulous location, well-stocked with amenities, great gym, wonderful view, small but very comfortable, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walt K. CA $84 CA $327 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Chicago-Hotels-Majestic-Modern-Style-Beach-Front-Rooftop-WFH-Gym.h103560718.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=2025-11-16&endDate=2025-11-17®ionId=553248635074842823&adults=2&location_highlights_explore=on_lake&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Hyatt Place Chicago-South/University Medical Center](//images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "Just an overnight stay for a college campus visit, but had the Hyatt recommended by numerous people and it didn't disappoint. What a great community the Hyde Park area was. Rooms were very nice, big and extremely clean. Will definitely be making that out go to for all future trips to the Chicago land area" [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chinatown Hotel Chicago](//images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "Lots of affordable parking in the area and right by the red line" [](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.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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