Planning your travel around annual events in Chicago can be a great way to lock in a one-of-a-kind vacation experience, get a feel for the real spirit of the city and connect with local residents. The Windy City puts on so many unique events each year that you’ll have lots of tempting options to choose from, no matter when you plan your trip. Here are a few favorites to help kick-start your travel plans. These represent only a small sampling of Chicago events; there are many more smaller fairs and festivals each year.
April: Chicago Improv Festival
The famous Second City improv troupe got its start in Chicago in 1959 and expanded from the Midwest to Los Angeles and Toronto. Chi-Town pays homage to stars that got their start at the original location with the annual Chicago Improv Festival, which focuses on workshops for actors and includes performances. Held in late April, the festival showcases improv and sketch comedy troupes from around the world on multiple performances. Lots of local talent represents, so you’ll get a taste for Second City’s talent.
June: Chicago Pride Parade
June is Gay Pride Month and Chicago Pride is one of the Midwest’s largest LGBT celebrations. There are events celebrating LGBT history throughout June, leading up to the parade on the last Sunday in June. Watch the city’s “Gay Idols,” an American Idol-style amateur singing competition, attend LGBT advocacy workshops, dance your booty off at local clubs and bars and watch or participate in the parade by marching with a local organisation.
August: Ginza Holiday – Japanese Cultural Festival
Held in Historic Old Town Chicago, the Ginza Festival showcases Japanese culture. Catch a local band playing a combination of American blues and traditional Japanese folk music, take in taiko drumming troupes and watch craft demonstrations from Waza, master Japanese craftsmen skilled in traditional crafts that hark back 300 years to Japan’s Edo period. Sample Japanese food, including udon noodles, edamame, sushi and chicken teriyaki. On Ginza Festival dress-up days, come dressed as your favorite anime character or in traditional Japanese clothing. The Ginza Festival occurs the second weekend in August.
November: Magnificent Mile in Lights
The Magnificent Mile boasts some of Chicago’s best shopping and dining and, in November, you can help turn it into a winter wonderland. Stroll the Magnificent Mile under thousands of twinkling lights or prepare for the holidays to come at the 450-plus shops, including Glove Me Tender, Henri Bendel and Marbles: The Brain Store. The Drake Hotel offers a special holiday tea, and the John Hancock Observatory welcomes Santa’s annual visit. See Disney characters, listen to marching bands or take in popular musical acts that will entertain children and adults alike.
Chicago offers a wealth of entertainment opportunities throughout the year. Enjoy a hearty laugh during improv performances, celebrate LGBT community during Chicago Pride, learn about Japanese culture and shop ’til you drop! You can also visit the Windy City for any number of other recreational outings so why not start planning early to make the most of your Chicago vacation.
Have fun!
Jessica loves traveling and visiting new places. She enjoys spending time outdoors and writing in her free time.









