The City of Waukegan has a humid continental climate with large temperature differences between seasons. Summers can be hot and humid, and winters can be severe. For the last three decades of the 20th Century, temperatures ranged from an average high of 28°C (82°F) in July to an average low of -11°C (12°F) in January.

The historic Genesee Theatre is a major attraction in the Port of Waukegan. Today, the theatre hosts musicals, concerts, comedy performances, and classic movies. Located in the Port of Waukegan's historic downtown, the building opened in 1927 featured a movie house and performance venue as well as apartments and retail space. When the theatre opened, it boasted 1200 yards of beautiful tapestries, a huge Barton Grande pipe organ, seven tons of marble, and 1800-seat capacity.

The Genesee Theatre was neglected, standing vacant from the late 1980s until 2001 when a major $23 million renovation was started. Part of the Port of Waukegan's downtown renovation project, 120 volunteers came forward to help bring the Genesee Theatre to its original state, carefully matching the original wall fabrics, wallpapers, and paint. Many wooden railings, plaster moldings, and light fixtures have been preserved, and the modern marquee is an exact replica of the original.

Today, the Port of Waukegan's state-of-the-art Genesee Theatre is a 10.6 thousand square meter (115 thousand square foot) facility with huge lobbies, comfortable lounges, an over-sized stage, and expanded seating capacity of 2400 seats. An 18-foot Baccarat crystal chandelier graces the grand lobby.

The Jack Benny Center for the Arts in the Port of Waukegan is home to the county's only opera company. Located in beautiful Bowen Park, the Center features the Waukegan Symphony Orchestra and Concert Chorus. The Center is also home to the Port of Waukegan Park District's Cultural Arts Division. In addition to performances, the Jack Benny Center for the Arts also offers training in theater, music, dance, art, and crafts. Lectures are also held in through the Bowen Heritage Circle.

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