Chicago Loop Insights

Chicago’s 11th Annual Arts in the Dark Halloween Parade Shines a Spotlight on the City’s Cultural Landscape

September 19, 2025

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.

Things to Do

Christkindlmarket Returns to Three Locations in 2025

August 28, 2025

2 MIN READ: The Christkindlmarket is delighted to announce the return of its cherished holiday tradition for its 29th season at Daley Plaza in Chicago, with new special activations.

Stay Things to Do

NASCAR Chicago Street Race: Loop Events, Traffic Impacts & Tips

June 27, 2025

5 MIN READ — Whether you’re visiting the Loop for NASCAR or you’re a local looking to plan the perfect weekend, we’ve got you covered. From can’t-miss events to traffic updates, here’s everything you need to know about what’s happening in the Loop during NASCAR weekend.

Eat + Drink

Best Rooftops in the Loop

June 3, 2025

3 MIN READ – Take your night to a whole new level at one of the Chicago Loop’s finest rooftop bars, offering some of the best views in the city.

Loop News Stay

Falling for the Loop and Sundays on State, celebration of arts and culture

June 2, 2025

3 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.

Stay Things to Do

The Official Start to Summer: Memorial Day Weekend in the Loop

May 14, 2025

2 MIN READ – Memorial Day weekend is a time to honor those who have served and sacrificed for our country. It also marks the start of summertime activities in the city! There are plenty of things to do in the Loop this Memorial Day weekend, and we’ve rounded up your best options.

Things to Do

Hop on over to these Easter and Passover activities in the Loop

April 11, 2025

2 MIN READ – Hop into the Chicago Loop this Easter and Passover season for an egg-cellent adventure with your friends and family! With plenty of egg-citing events and activities, you’re sure to have an un-bunny-lievable time.

Things to Do

Honor Martin Luther King Jr. Day in the Loop

January 17, 2025

2 MIN READ – Every third Monday of the year, the U.S. honors and celebrates the legacy of activist Martin Luther King Jr. Participate in various engagements happening in the Loop this weekend to honor MLK Day.