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The Best Chicago Events: What to See and Do in 2019

Chicago is a city that is full of fun things to do year around. From festivals to parades, concerts, and annual celebrations, this year is sure to be full of fun events both old and new.

Check out the release dates for some of the city’s biggest annual events and plan your calendar accordingly.


January 25th – February 7th: Chicago Restaurant Week. Chicago Restaurant Week returns for two weeks of dining deals from hundreds of celebrated restaurants all across the city. Search participating restaurants, view menus and book your reservations here.

February 7th – 17th: Chicago Theatre Week. Choose from more than 100 productions and sample the extraordinary range of theatrical offerings in Chicago. Learn more about Chicago’s dynamic theater scene and Chicago Theatre week here.

February 9th – 18th: Chicago Auto Show. The Chicago Auto Show. The nation’s largest auto show features nearly 1,000 different vehicles of domestic and imported passenger cars, trucks, SUVs, experimental and concept cars. For more details visit Chicago Auto Show.com.

February 24th: Chicago Volunteer Expo. There are so many ways to give back to your community in 2019.  Visit over 85 nonprofit organizations from all over the city to learn how you can lend a hand. Learn how you can get involved by visiting the event page.

March 6th – 10th: Alvin Ailey. The legendary multi-cultural company commemorates their 60th anniversary — and the 50th anniversary performing at the Auditorium Theatre in Chicago. For more tickets to the renowned dance tradition, visit the website here.

April 12th – 14th: Black Women’s Expo. Now in its 25th year, the Black Women’s Expo (BWe), originating in Chicago, offers unparalleled opportunities where she finds the latest trends, amazing new products and services, where she gets informed, empowered and enlightened. Learn more by visiting the website here.

May 26th: Bike the Drive. Bike car-free along Lake Shore Drive during the 18th annual Bike the Drive event. Learn more about the event here.

May 31st – June 1st: Chicago Gospel Music Festival. Celebrating the great influence of the music genre born in this city 80 years ago, the Chicago Gospel Music Festival features local and national artists from traditional choirs to contemporary urban styles at the largest free, outdoor gospel music festival of its kind. For more details on this festival, visit the website.

June 7th – 9th: Chicago Blues Festival. With a diverse lineup celebrating the Chicago Blues’ past, present and future, the Chicago Blues Festival features the live music performances of over 100 national, international and local artists celebrating the city’s rich Blues tradition while shining a spotlight on the genre’s contributions to soul, R&B, gospel, rock hip-hop, rap and more. Visit the website to learn more about this highly anticipated festival.

July 10th – 14th: Taste of Chicago. Taste of Chicago is the nation’s premier free outdoor food festival showcasing the diversity of Chicago’s dining scene, alongside a smorgasbord of cooking demonstrations, music concerts, dance performances, art activations, family activities and more. For more details, visit the website.

July (TBD): 16th Annual Silver Room Block Party. All though no date has officially been announced it can be assumed that the Silver Room Block Party will be back in the Hyde Park neighborhood on the 3rd week of July. The outdoor celebration of music, community, art, love, and culture attracts a crowd from all parts of the city and country. For more information and to view photos of last years event, visit the website here.

July 20th – 21st: ComplexCon. ComplexCon is a haute new event hitting Chicago this summer and is bringing a lot of hype. highlights the best the world has to offer in pop culture, music, style, art, food, innovation, activism, and much more. Expect ComplexCon Chicago to bring that same energy to the Midwest, while simultaneously celebrating the city’s influence on the cultural landscape. Keep up to date on more details including ticket sales for ComplexCon Chicago by visiting the website here.

August 17th – 18th: 61st Annual Chicago Air and Water Show. The Air and Water show features military and civilian flight aerobatics, historic aircraft, simulated water rescues, and parachute teams, the Chicago Air and Water Show is one of the largest and longest-running free admission events of its kind. For more information, visit the website here.

August 23th – September 1st: Chicago Jazz Festival. The Chicago Jazz Festival showcases the greatest jazz artists from Chicago and around the world across the city during new, extended festival dates. The Chicago Jazz Festival is produced by the Department of Cultural Affairs and Special Events and programmed by the Jazz Institute of Chicago. Get more details on the annual event here.

September 19th – 22nd: EXPO Chicago. International exhibitors present alongside one of the highest quality platforms for global contemporary art and culture. For more information, visit the website here.

September 13th – 29th: World Music Festival Chicago. Enjoy global grooves by award-winning artists from around the world at the city-wide, multi-venue World Music Festival Chicago featuring 50 artists and ensembles representing over 20 countries and regions of the world. For more details, visit the event page here.

September 27th – 29th: Chicago Gourmet. Chicago Gourmet, the nation’s premier culinary experience that takes place annually in Millenium Park. For more details on the highly anticipated event, visit the website here.

October 12th – 13th: Open House Chicago. The annual event held by the Chicago Architecture Center. Open House Chicago (OHC) is the city’s annual celebration opens the doors of some of the city’s most iconic and unique architectural treasures. Learn more by visiting the website.

October 14th – 20th: Chicago Ideas Week. A unique nonprofit platform designed to inspire action through entertaining and accessible events, grassroots initiatives and thought-provoking content that fosters connectivity, crosses industry and social boundaries to spark ideas into action. Citywide Locations. Learn more here.

October 19th: Chicago Marathon. Bank of America Chicago Marathon welcomes thousands of runners from more than 100 countries and all 50 states. The race’s iconic course takes runners through 29 vibrant neighborhoods on an architectural and cultural tour of Chicago. Learn more about the annual event here.

November 15th – January 6th, 2020: 106th Christmas Tree Lightening and Holiday Celebrations. Celebrate the holiday season at the official Chicago Christmas Tree Lighting, sing holiday favorites at Caroling at Cloud Gate on Friday evenings and glide across the McCormick Tribune Ice Rink. For more information, visit the website here.

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