Chicago’s diversity and beauty has seen it ranked among the best 15 cities on the planet last year, not to mention once again taking top spot in Condé Nast Traveler’s Best Big City in the United States ranking.
Our world-class city is constantly impressing on a global scale with a remarkable range of landmarks and public art, an eclectic and esteemed collection of museums, and an array of internationally-renowned bars and restaurants.
Another thing that makes Chicago so incredible is its unique events and activities that take place throughout the year. With a beautifully diverse and dynamic population, the city celebrates its identity with all manner of parades, parties, and celebrations that range from raising money for charity and honoring heritage to enjoying triumphant traditions that trace back decades.
Whether you’re a seasoned local or a thrill-seeking visitor, these are the 10 important annual dates and unique Chicago events that should not be missed over the year.
1. Chicago Restaurant Week (January-February)
Every year, award-winning culinary Chicago restaurants participate in Chicago Restaurant Week. The 17-day celebration includes over 350 restaurants offering special fixed-price deals on brunches, lunches, and dinners across the city.
Dates: This year from January 19 to February 4.
2. St Patrick’s Day (March)
With a historically large Irish population in a diverse and wonderful city like Chicago, it’s no surprise that our St. Patrick’s Day celebrations are of international renown.
By far the most famed feature of this day is the river dying which has taken place in Chicago for over 60 years. Usually taking place the Saturday before St Patrick’s Day (March 17th), the annual tradition sees the Chicago River turn emerald green using an environmentally friendly vegetable-based dye.
Thousands of people then line riverwalk spots and crowd bridges to get a glimpse of the iconic occasion unraveling which is then followed by parades and Irish festivities including marching bands, bagpipes, dancers, and a whole explosion of green across Chicago.View our green river dying gallery.
Dates: Weekend March 16-17
3. Chicagohenge (March and September)
One of Chicago’s most unique experiences twice a year during the spring and autumn equinoxes offering an extraordinary collaboration between the magic of nature and Chicago’s glorious architecture.
You’re likely familiar with the prehistoric boulder formation in Wiltshire, England. During the summer and winter solstice, the sun rises behind Stonehenge’s Heel Stone, where its rays are captured within the rock frame, creating a glorious spectacle that thousands of people flock to witness
In Chicago, the equinoxes provide a similar sight right here in our urban metropolis. Dubbed “Chicagohenge“, twice a year the sun lines up directly with Chicago’s streets and beams down the heart of the city splashing through Chicago’s artificial valleys.
Dates: March 21 and September 22
4. Chicago Pride Parade (June)
Pride Month is celebrated each year in June to honor the 1969 Stonewall Uprising in Manhattan, a tipping point for the Gay Liberation Movement in the United States.
An array of events take place across the country each June celebrating our nation’s wonderful LGBTQ+ community and Chicago’s Pride celebrations are among the largest in the world.
An enormous parade that has been taking place for over 50 years now features more than 200 colorful entries and travels over 20 blocks through Chicago.
The weekend before is another important Chicago date when a two-day street festival Chicago Pride Fest® offers live music on 3 stages, drag performances, dance exhibitions, and more than 150 food and merchandise vendors.
Dates: Sunday, June 30.
5. The Chicago Ducky Derby (August)
Every summer, over 60,000 yellow ducks splash away in the Chicago River in a lip-biting race to the finish line to raise money for Special Olympics.
Thousands of Chicagoans flock to the downtown area to watch the spectacle and many adopt ducks for $5 each or go big with a Quack Pack (six ducks) for $25! The event raises upwards of $300,000 for over 20,000 athletes and more than 10,000 young athletes.
The annual Chicago Ducky Derby usually takes place on the second Thursday of August from the Columbus Drive Bridge on the Chicago River.
Dates: Second Thursday of August
6. Chicago Air and Water Show (August)
One of the most popular summer events can be found in the skies above Chicago. The Chicago Air and Water Show has been wowing spectators lined up along North Avenue Beach and the Lakefront from Fullerton to Oak Street every August since 1959.
Presented by the City of Chicago it is the largest free show of its kind in the entire country often attracting more than 2 million people to watch both civilian and military pilots perform over the lake.
The amazing aeronautic spectacle often includes performances from the Navy Blue Angels and the Golden Knights Army Parachute Team as well as an array of revered daredevil pilots, parachute groups, boat demos, diving stunts, and many more events.
The Chicago Air and Water Show usually takes place on the third weekend of August from 10 am until 2 pm on both Saturday and Sunday.
Dates: Usually late August
7. Bud Billiken Parade (August)
The Bud Billiken Day Parade is the largest African-American parade in the United States and has been held in Chicago every summer since 1929.
Taking place on the city’s south side on the second Saturday in August, it travels on Dr. Martin Luther King Drive through Bronzeville and Washington Park finishing with a picnic and festival in Washington public park.
According to a dedicated website, the parade unites African-Americans throughout the city of Chicago in music, dance, food, and laughter while commemorating the past and celebrating the future.
Over the years the parade has featured celebrities, politicians, and numerous organizations who all come to celebrate youth, education, and African-American life.
Dates: Every second Saturday in August
8. Taste of Chicago (September)
Of all the free activities and events in Chicago throughout the year, few offer such an iconic and eclectic experience as Grant Park’s long-running Taste of Chicago.
Established in 1980, the uniquely Chicago summertime tradition features numerous food vendors and trucks, all showcasing the diversity and world-class talent of Chicago’s culinary scene in the city’s most beloved park.
With an array of live music acts, the free Chicago festival has fast become one of the city’s most cherished annual traditions with more than a million attendees in recent years.
Dates: Usually early September
9. Christkindlmarket Chicago (November-December)
Chicago’s German-inspired annual Christmas market is one of the city’s most beloved annual activities once the city begins revving up for the holiday season in November.
The famed German-style outdoor market now takes place at Daley Plaza, Wrigleyville, and Aurora each year usually from around the third weekend of November until the end of the year.
Guests can peruse handmade gifts to the magic of festive music while enjoying German food and beverages like roasted nuts, fresh pretzels, bratwurst, and hot spiced wine all in the coziest of atmospheres!
Note: The market usually opens the same weekend that the Millennium Park Tree Lighting Ceremony takes place. Marking the start of the festive season, the great tree illuminates the intersection of Michigan Avenue and Washington Street thereon and the ceremony is certainly another important event in the calendar year.
Dates: From late November
10. Chicago NYE Firework Show (December)
Ring in the New Year with a breathtaking fireworks display over Lake Michigan. A magnificent NYE fireworks display lights up Chicago skies every year launching from several different barges and bridges along the Chicago River and over Navy Pier.
Dates: December 31st
Art on theMART programs (Spring, Summer & Fall)
Holding the title of the “largest permanent digital art projection in the world”, Art on theMART attracts thousands to the Riverwalk and Wacker Drive in downtown Chicago every week by transforming the 2.5-acre river façade of the Merchandise Mart with prismatic moving art projections.
Using 34 digital projectors the 25-story-tall face of the Merchandise Mart is brought to life for nightly 30-minute shows from April through December offering an incredible spectacle in the heart of Chicago.
As well as being a free experience with rotating seasonal programs, Art on theMART provides a public platform for local artists, national artists, and international artists with work ranging from schools to renowned exhibitions and everything in between for much of the year.
Sundays on State (July and August)
In 2021, with the pandemic still lingering Chicago Loop Alliance announced an exciting new project to “bring people safely back to the Loop”.
The project was an ambitious weekly summer street festival that closed off State Street from Lake to Madison on Sundays throughout the summer. Called ‘Sundays on State’, the event aimed to revive the Loop’s economy with a wide range of attractions and activities that would give pedestrians “a chance to experience arts and culture, active recreation, retail, restaurants, and bars against the backdrop of State Street’s iconic architecture.”
Dubbed as a trial in 2021 with hints that it could become a regular summer occurrence depending on how it went, Sundays on State returned with an expanded footprint in 2022 and then on two select dates in 2023 due to its hugely successful inaugural years.
The free, interactive block party features art, culture, shopping, dining, and more but dates are not set in stone until closer to summer.
Dates: During summer but not yet set
[Featured image from Shutterstock]