Chicago Loop Insights

Feel the Valentine’s Day Love in the Loop

January 30, 2026

6 MIN READ – It’s a day for love, and there’s few places like being in the Loop to keep your romance alive. Celebrate love with intimate and enjoyable experiences downtown.

Stay Things to Do

Loop favorites during Chicago Theatre Week

January 30, 2026

5 MIN READ – Chicago Theatre Week (CTW) has become a staple in the city, especially in the Loop’s theatre district, and returns for its 13th year, February 6-16, 2025.

Loop News Stay

Renewed investment, holiday activity round out final 2025 quarter

January 15, 2026

3 MIN READ — Chicago Loop Alliance (CLA) released its quarter four 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.

Loop News Stay

Arts and culture continue to charge Loop’s economic engine

October 10, 2025

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.

Loop News Stay

Chicago…best big city in the U.S., nine years running

October 9, 2025

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.

Stay Things to Do

All you need to know to enjoy Lollapalooza weekend

July 25, 2025

3 MIN READ – There’s nothing quite like it. One of the nation’s largest music festival, Lollapalooza, takes place July 31- August 3 in the Chicago Loop, and this year’s lineup lineup includes Tyler the Creator, Olivia Rodrigo, Twice, Sabrina Carpenter, A$AP Rocky, and many more.

Loop News Stay

Arts and leisure tourism, coupled with strong investment, boost Q2 Loop economy

July 16, 2025

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.

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.