Title: Shop travel - Expedia.co.uk - ![](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 Lakeside Hotels Tonight [5 Dec - 6 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-05&endDate=2025-12-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [6 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-06&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [12 Dec - 14 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Lakeside Hotels ![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) ![Interior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1280h1921x0y2-c0095f7f.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) ### Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6 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. £154 includes taxes & fees 9 Dec - 10 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Sunflower-Apt-12-Min-From-Downtown-CHI.h91086437.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/a9c979ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.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 Downtown Chicago 9.4/10 Exceptional (2254) "Perfect environment and location" ![China](https://a.travel-assets.com/egds/marks/flags/cn.svg) YIWEI £106 includes taxes & fees 23 Dec - 24 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Premium bedding, down duvets, pillow-top beds, in-room safe](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) ![Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.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) ### The Wade Downtown Chicago 8.4/10 Very good (1501) "Great location, walkable to so many area attractions. Would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie £84 includes taxes & fees 10 Dec - 11 Dec [](https://www.expedia.co.uk/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Room, Multiple Beds (The Drake Residence) | Living area | 48-inch flat-screen TV with cable channels, TV, pay films](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 | 48-inch flat-screen TV with cable channels, TV, pay films](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 (1353) "Beautiful hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marcia £105 includes taxes & fees 11 Dec - 12 Dec [](https://www.expedia.co.uk/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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/cc9f9fd8.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) ### Waldorf Astoria Chicago Downtown Chicago 9.4/10 Exceptional (1002) "Absolutely fantastic hotel great service, you couldn’t ask for more." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) J Michael £349 includes taxes & fees 21 Dec - 22 Dec [](https://www.expedia.co.uk/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) ![Free self-parking](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/b5958a34.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 (1002) "Great stay in clean modern room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Douglas £160 includes taxes & fees 30 Dec - 31 Dec [](https://www.expedia.co.uk/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) ![Indoor pool, pool loungers](https://images.trvl-media.com/lodging/1000000/50000/49500/49450/54b051c1.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) ![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 (1003) "Nice hotel would definitely stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ANGELA £124 includes taxes & fees 10 Dec - 11 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Lodge.h49450.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) ![Exterior](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/1dd62bdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1350h899x0y1-beef26b6.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 Lawndale 10/10 Exceptional (8) "Very nice apartment close to downtown!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dariana £158 includes taxes & fees 9 Dec - 10 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-Boho-Chicago-10-Min-To-Chicago.h105552490.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/918c1b0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/a16e8e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/fbb710a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/d19de994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 15mins DT | Wicker Park Gem | Sleeps 7 | FreePark East Garfield Park £220 includes taxes & fees 14 Dec - 15 Dec [](https://www.expedia.co.uk/Chicago-Hotels-15mins-DT-Wicker-Park-Gem-Sleeps-7-FreePark.h116934319.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) ![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) ![Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/2e0ab6dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency McCormick Place Chicago Near South Side 9.2/10 Wonderful (1032) "Great stay. Staff was wonderful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debra £175 includes taxes & fees 14 Dec - 15 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.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=2025-12-19&endDate=2025-12-20®ionId=553248635074842823&adults=2&location_highlights_explore=on_lake&sort=RECOMMENDED&openPlayBack=true) ## Find out more about South Side ## Top South Side Hotel Reviews ## Explore a world of travel with Expedia