The historic river valley towns of Illinois have plenty of fun cultural festivals throughout the summer and fall months. These are mainly low-key family affairs based around local food, wine, music, and heritage. The really big events in Illinois occur in Chicago, which has a superb schedule of festivals, concerts, and conferences throughout the year. Illinois holidays are celebrated throughout the state with observance of national events like the 4th of July and Memorial Day.

Chicago Air & Water Show

Every August, two fun days of air and water excitement come to Chicago’s North Avenue Beach. This free event is really popular as Lincoln Park’s waterfront shows off all kinds of cool water craft and aerial tricks. The highlight is the US Navy Blue Angels jet formation flight and the Golden Knights parachute team from the US Army as they somehow weave through the city’s skyscrapers to land at the beach.

North Michigan Avenue Art Festival

For three days in July, Chicago’s Pioneer Court transforms into an outdoor art gallery showcasing the works of both famous and unknown Illinois artists. Works by more than 200 painters, potters, sculptors, and photographers are on display with artists ready to sell their unique creations.

Ravinia Festival

This hugely popular music festival extends for three solid months from early June until early September. It is held in Highland Park, a 30 minute drive north of Chicago and features a constant stream of live outdoor concerts that range from hot bands to classical symphony music and everything in between. Picnic on the lawn and enjoy music in the balmy summer evening. The park is easily accessible via Metra train from downtown.

Viva! Chicago Latin Music Festival

Each September, this major music and culture event takes over Chicago’s Millennium Park, attracting around 150,000 visitors. Latin bands from across the Americas come to take park in this famous festival, supported by hordes of Latin food and drink vendors and the whole thing is free to the public.

Chicago Jazz Festival

Another major musical event each September is the free jazz festival, which attracts big names and up-and-comers to Illinois alike to the outdoor stages at Millennium Park and Grant Park. Sit on the lawn and enjoy the free moody tunes, and if you’re a real jazz fan, be on the lookout for hot after-hours jazz sets at all the city’s top bars and clubs.

Chicago International Film Festival

America’s longest-running competitive film festival, the Chicago International Film fest began in 1964. More than 100 flicks in all genres are screened at theaters all around the city every October. There’s a big emphasis on international films, bringing some rare treats from around the globe to the city’s screens. Famous actors and directors also make appearances at premier events.

Chicago Thanksgiving Parade

Started way back in 1934, this is one of America’s oldest Thanksgiving Day parades and only New York’s parade even comes close. Illinois actually has more floats, balloons, and marching bands. The parade romps up State Street for several blocks as 350,000 people watch on the sidewalks in the nippy November air.


For three days the first weekend of August, Chicago’s biggest musical event of the year rivals fests around the country like Bonaroo and Coachella. Started twenty years ago by rocker Perry Farrell of Jane’s Addiction, major acts and headliners make their way to Grant Park. Spread out over 115 acres and multiple stages, 130+ artists a year run the gamete from pop, rap and alternative to an especially rocking DJ tent.