Your insider's guide to the best things to do, see, and experience in Chicago.
5 MIN READ – One of the nation’s largest music festivals, Lollapalooza, takes place July 30-August 2, 2026, in the Chicago Loop. This year’s lineup includes Charli XCX, Olivia Dean, John Summit, Lorde, Jennie, The XX and more. Here is everything you need to know.
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.
5 MIN READ – Mayor Brandon Johnson and the Department of Cultural Affairs and Special Events (DCASE) announced today the 2025 lineup of spring and summer festivals and events starting this May, showcasing the city’s vibrant arts, culture and community spirit.
4 MIN READ – El Grito Chicago, a vibrant 2-day festival in celebration of Mexican Independence Day, announces an exciting entertainment line-up made up of national and local performing artists from multiple musical genres. El Grito Chicago will take place in the Chicago Loop at Butler Field in Grant Park on Saturday, September 14 and Sunday, September 15, 2024, from 2-10 p.m.
4 MIN READ – NASCAR Chicago Street Race announced that it will partner with Chicago Loop Alliance and JoRand (founded by local restauranteurs Victor Love and Mark Rand) to expand this year’s NASCAR Village, the free, public experience in Butler Field throughout race weekend.
4 MIN READ – There’s no sweeter way to see the Chicago Loop than from a bicycle (or a scooter, or a skateboard, or any of those other crazy little things you see in the bike lane!). Whether you’re getting back to work, coming in for fun, or you’re already here and you need a quick way to get from A to B, here are some tips for biking to the Loop.
3 MIN READ – Chicago, like the rest of the United States, is experiencing an unprecedented bike boom as people seek out both an open-air mode of transportation and a fun activity that gets them out of the house. Also, mass bike commuting is a great way to keep vehicle congestion to a minimum. For any new riders—or riders who are new to cold weather—follow these tips on how to transition to winter-weather cycling. It’s a great way to get back in the Loop.
4 MIN READ – Following the success of the inaugural event, Chicago will welcome the NASCAR Cup Series back to Grant Park on Sunday July 7, 2024 at 3:30 pm CT, with the NASCAR Xfinity Series set to return on Saturday, July 6, 2024 at 1:30 pm CT, with both races broadcast on NBC for the first time.
March 15, 2026
Chicago’s top-rated architecture boat tour, 90 minutes with expert CAC guides, stunning skyline views, open-air seating, and onboard amenities.
March 21, 2026
Explore Chicago’s haunted past on a nighttime river cruise featuring ghost stories, mob history, and eerie secrets of the Windy City.
April 17, 2026
Chicago River & Lake Michigan cruise with skyline views, iconic landmarks, and engaging guides sharing the city’s history and stories.
April 17, 2026
Experience Chicago at night on a 90-minute river and lake cruise, featuring a glittering skyline, cool breezes, and lively, family-friendly commentary.
April 22, 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…
May 23, 2026 | 8:00 PM – 10:00 PM
Cruise from the Chicago Riverwalk to Lake Michigan for skyline views and a 3D-enhanced fireworks show with music and narration.
June 1, 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…
June 30, 2026
An exciting lineup of outdoor films on Tuesdays this summer.
