Experience Quality Amenities at Our Hotel in Oswego, IL This recently remodeled Holiday Inn Express hotel in Oswego, IL is conveniently located in the far western suburbs of Chicago near Aurora, Montgomery, Yorkville, Plainfield, Sugar Grove and Naperville. Surrounded by I-88 to the north, I-355 to the east and I-55 to the south, you'll find small town hospitality and easy access to the big city. Leisure guests love that we are only 40 miles from the bustling streets of Chicago and its great attractions. Guests can visit exciting local attractions, such as Hollywood Casinos, Paramount Arts Center and Raging Waves Waterpark, which are all located near our property in Oswego. Our hotel's patrons should also plan to visit the famous Walter Payton's Roundhouse where you can enjoy great food, beer and entertainment.