Chicago Annual Events

Winter Celebration in Lights

January 2021

Winter Celebration in Lights takes place during the first week of January at the Garfield Park Conservatory. Holiday revelers can view sparkling lights and beautiful plant displays located in the largest glass greenhouse in the world. Kids can also enjoy interactive events in the Elizabeth Mores Genus Children’s Garden.

Winter Flower and Train Show

January 2021

Winter Flower and Train Show located at the Lincoln Park Conservatory, is a place where visitors can observe flowers or take an exciting train ride through a decorated Christmas town, through the first week of January.

Coyote Winter Festival

February 2021

During the first week of February, Around the Coyote Winter Festival takes place. This is an annual event sponsored by the local artists where participants can walk through a studio and get a chance to view the works of over 400 artists.

Chicago Auto Show

February 2021

The Chicago Auto Show, located at McCormick Place Convention Center, is the largest in North America. The Auto show jumps off for two weeks in the middle of February. This event will showcase multiple exhibitions, which include a variety of imported and domestic passenger cars, trucks, and SUVs. Approximately 1,000 different vehicles will be displayed.

Chicago Flower and Garden Show

March 2021

The Chicago Flower and Garden Show is held at the Navy Pier during March. Attendees can attend free seminars and experience over 100 exhibitors showcasing landscaping, garden, and horticultural products. There will be plenty of bright, cheerful flowers to be admired.

Chicago Underground Film Festival

May 2021

Chicago Underground Film Festival is an annual cultural event hosted at the Gene Siskel Theater in May. This event offers independent filmmakers a venue to showcase their work. Photography, drawings, and movie poster art are also showcased.

Chicago Blues Festival

June 2021

Every summer, during the first week of June, the Chicago Blues Festival takes place at Grant Park. This is a free music festival that lasts for three days and takes place on five different stages. Various blues artists from all over the country visit Chicago to perform at this event.

Chicago Jazz Fest

July 2021

The annual Jazz Festival is another free Chicago festival held during the summer at the Cultural Center in Millennium Park. This event is a favorite Labor Day tradition for locals, promoting an appreciation for all jazz forms through live performances. National and international artists are showcased along with Chicago’s outstanding jazz talent. The Jazz Festival strives to educate and encourage all ages of jazz audiences.


October 2021

Chicagoween is a time when the entire city of Chicago prepares for Halloween. The parks, streets, city, and buildings are decorated and filled with many family-friendly and fun activities for children: Franken Plaza, the Chicago Park District, and Navy Pier all host a variety of Halloween events.

Magnificent Mile Lights Festival

November 2021

The weekend before Thanksgiving, Chicago travelers can enjoy the holiday season at the Magnificent Mile Lights Festival. This free event continues over the course of three separate weekends. Over a million sparkling holiday lights will be hung in the trees on both sides of the Magnificent Mile. Revelers can expect plenty of fireworks, decorated floats, music, parades, and a festival atmosphere.

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