Your insider's guide to the best things to do, see, and experience in Chicago.
5 MIN READ — This December, Libby Dennen steps onto the stage as Anastasis in Beyond the Nutcracker, it’s more than a return — it’s a full-circle moment. Nearly a decade after first performing the role as a young student, the now–Ballet 5:8 Solo Artist brings to it the artistry, grace, and maturity shaped by years of growth on and off the stage.
4 MIN READ — Chicago Loop Alliance (CLA) released its quarter three 2025 State of the Loop report on downtown activity, using a variety of data sources, produced by CLA since July 2020. The report tracks pedestrian and transportation activity, investment, retail, arts and culture, and more.
5 MIN READ — Chicago has once again been crowned the Best Big City in the U.S. in the Condé Nast Traveler Readers’ Choice Awards, one of the most prestigious recognitions a destination can receive. This is the ninth consecutive year Chicago has claimed this title, a streak unprecedented in the awards program’s more than 30-year history.
4 MIN READ — Chicago Loop Alliance is announcing programming for the fall season under the campaign, Falling for the Loop, positioning the month of October as a celebration of arts and culture.
5 MIN READ: LUMA8 and the City of Chicago present the 11th Annual Arts in the Dark Halloween Parade—a family-friendly celebration featuring dazzling floats, larger-than-life puppets, and dynamic performances. The parade takes place on Saturday, October 18, from 6–8 p.m. along historic State Street, stepping off at Randolph Street. This event is also part of Chicago Loop Alliance’s Falling for the Loop fall programming.
2 MIN READ — The City of Chicago has officially approved the 2025 Chicago River Swim (CRS), marking the
first open water swim in the Chicago River in 98 years. Set for Sunday, September 21, 2025, this landmark
event will celebrate the city’s environmental progress and generate critical funds for ALS research and youth
swim education programs.
5 MIN READ: Chicago Loop Alliance (CLA) recently released its quarter two 2025 State of the Loop report on downtown activity, using a variety of data sources, produced by CLA since July 2020.
3 MIN READ — On July 19, My Block, My Hood, My City (MBMHMC) will host Downtown Day, a citywide event, aimed at bringing nearly 1,500 youth to downtown Chicago in an effort to expose Chicago teens to the dynamic opportunities of the Loop and downtown area. Over 30 downtown businesses will offer free or discounted attractions; intimate workshops; tours and culinary experiences.
marzo 14, 2026
Chicago’s top-rated architecture boat tour, 90 minutes with expert CAC guides, stunning skyline views, open-air seating, and onboard amenities.
marzo 20, 2026
Explore Chicago’s haunted past on a nighttime river cruise featuring ghost stories, mob history, and eerie secrets of the Windy City.
abril 16, 2026
Chicago River & Lake Michigan cruise with skyline views, iconic landmarks, and engaging guides sharing the city’s history and stories.
abril 16, 2026
Experience Chicago at night on a 90-minute river and lake cruise, featuring a glittering skyline, cool breezes, and lively, family-friendly commentary.
21 de abril de 2026
Directed by Andrew Scoville. Co-created by Academy, Grammy, and Tony Award-winning artist David Byrne* and writer Mala Gaonkar, Theater of the Mind is a new theatrical…
mayo 23, 2026 | 3:00 PM – 5:00 PM
Cruise from the Chicago Riverwalk to Lake Michigan for skyline views and a 3D-enhanced fireworks show with music and narration.
mayo 31, 2026
Let your creative potential shine this summer with a class at the School of the Art Institute of Chicago, with options available for kids, teens and…
junio 5, 2026
From June 6th until July 5th, the phenomenal Champions of Magic bring their acclaimed illusion spectacular to Chicago. Featuring their biggest illusions ever, experience the Broadway-scale…
junio 19, 2026
MUSIC BY MARK HOLLMANNLYRICS BY MARK HOLLMANN AND JAY REISSBOOK BY ERIN QUINN PURCELL AND JAY REISSDIRECTED BY MARC BRUNISTARRING…
