10 Best Annual Events In Chicago

The best annual events in Chicago consists of concerts, parades and festivals. The city of Chicago is home to annual events and many of the festivities are free to the public. The annual events held in Chicago are some of the biggest in the country and people come from all over the world to enjoy what Chicago has to offer.

  1. Lollapalooza. The biggest annual music event in Chicago takes place in Grant Park at Lollapalooza. The three day and night event, which always occurs the first weekend in August, brings in big musical performers. The Lollapalooza music festival was a traveling tour that started in 1991, but in 2005 the festival claimed Chicago as its home for the annual music event.
  2. Taste of Chicago. The world's largest food festival takes place annually at Taste of Chicago held in Grant Park. The ten day event is held the last week in June through first week in July. Over sixty restaurants showcase food and drinks which can be bought in portions. Free concerts are held at Petrillo Music Shell by local and world known music artists. The main entrance is Michigan Avenue at Congress Drive. The event runs daily from 11 a.m. to 9 p.m.
  3. Chicago Blues Festival. The largest free blues festival is held annually at Grant Park in Chicago during the second weekend of June. The Chicago Blues Festival started in 1984 and has evolved to four days of blues music on six stages. Admission is free and is held in Chicago's Grant Park from 11 a.m. until 9:30 p.m.
  4. Air and Water Show. Starting out as Family Day Celebration in 1959, the annual Chicago Air and Water Show has become the largest spectator event in the United States. Over two million people watch the annual Air and Water Show which takes place along North Avenue Beach the second weekend of August.
  5. Chicago Jazz Festival. The annual Chicago Jazz Festival is held the week before Labor Day in Grant Park. The Chicago Jazz Festival officially started in 1979 between the Jazz Institute of Chicago, Chicago's Council of Fine Arts and musicians. Jazz music fans sit on blankets and chairs to watch the two day free admission event.
  6. Auto Show. Chicago's first Auto Show took place in 1901 at the Chicago Coliseum and showcased vehicles for an entire week in March. Currently, the Chicago Auto Show is held at McCormick Place, which has 1.2 million square feet to showcase 1,000 vehicles in February.
  7. Pride Parade. The Chicago Gay and Lesbian Pride Parade happens annually the last week of June in East Lakeview, Chicago since its start in 1970. The parade starts off on the corner of Halsted and Belmont at noon and ends in Lincoln Park. Awards are handed out to participants and the parade is free for the public to attend.
  8. Pitchfork Music Festival. This annual music event in Chicago has been held at Union Park since its 2006 creation. The three day event showcases over 40 bands on three stages during the middle of July. The annual event was created to showcase independent bands in a big festival setting while maintaining low ticket prices. Children under the age of ten years old are allowed in for free with an adult.
  9. Underground Film Festival. Chicago's best annual event for movies is the Underground Film Festival which is held at Gene Siskel Film Center. The largest underground film festival in the nation belongs to Chicago where people enjoy independent features, documentaries and experimental films. Anyone can submit a film for consideration to be shown. Awards are given out for best narrative feature, narrative short, experimental, animation and more.
  10. Magnificent Mile Lights Festival. The holiday season is kicked off in Chicago every November since 1959 with the annual Magnificent Mile Lights Festival. At this annual Chicago festival Grand Marshall Mickey Mouse taps his wand and lights up more than one million lights on 200 trees along Chicago's famous Magnificent Mile. Music is another part of the lights festival. The Harris Stage at 401 North Michigan Avenue provides free musical acts during the day.
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