Revel in the most glorious season of all
There’s something magical about Chicago in the summer. Everyone’s out and about, exploring the lakefront and the city’s parks, the mood is high, and the live entertainment is in abundance. Summer in Chicago is music festival season, after all—with something for everyone, no matter what’s on your most-played Spotify playlist. Need a little musical direction? Here are some of our favorite music festivals taking place across the Windy City this summer.
Free Shows
Millennium Park Music Series
Enjoy a lineup of R&B, pop, jazz, country, and more, just a short hop, skip and a jump from Arlo Chicago. The free outdoor concert series with city skyline views takes place at the iconic Jay Pritzker Pavilion, with shows on select Mondays and Thursdays throughout the summer. This year, the diverse lineup of performers includes Novos Baianos (July 21), Steel Pulse (July 24), Horsegirl (July 28), and Orchestra Resavoir (Aug 4). For a deliciously easy way to pregame or keep the vibes going post-concert, pop across the street to check out the New American dishes and craft cocktails at About Last Knife.
Grant Park Music Festival
The city’s only summer-long festival devoted to classical music celebrates its 90th season this year. The series features the Grant Park Orchestra and Chorus, and this year they’ll present classic symphonies, works by local Chicago composers, and a Rodgers and Hammerstein tribute. Most performances take place on Wednesday and Friday evenings from 6:30pm, and Saturdays from 7:30pm, at the Pritzker Pavilion. Keen to make a weekend of it? Might we suggest checking out Arlo Chicago’s Daily Drop? You might just be able to secure a room for the low rate of $125. A fresh batch of rooms are released daily, so you can try your luck and turn a classical music night into a city sleepover.
Chicago Jazz Festival
For more than 40 years, the Chicago Jazz Festival has brought musicians and jazz fans to Millennium Park for four days of live entertainment. Taking place from August 28–31 this year, the Jazz Festival will showcase jazz legends and up-and-comers alike. Just a few of the performers gracing the stage include Henry Johnson, Sarah Marie Young, Gary Bartz & NTU Troop, and the Natalie Scharf Quintet featuring Paul Asaro.
Neighborhood Fests
Fiesta Del Sol
Celebrate Mexican culture in the lively Pilsen neighborhood of Chicago at this multi-day festival from July 31–August 3. Savor authentic Mexican food from local vendors and bring the kids (or channel your inner kid) to partake in carnival rides and games. The weekend includes live music and entertainment on multiple stages.
Chinatown Summer Fair
This annual street fair takes place on Saturday, July 26 (11am–10pm) and Sunday, July 27 (10am–7pm). Head to Wentworth Avenue from Cermak Avenue to 24th Place to catch all the action. The 46th edition of the Chinatown Summer Fair will showcase lion dance processions, live music, and Chinese cuisine both traditional and contemporary. There’s a kids’ section, arts and crafts, and dance competitions including K-Pop and Bboy style dancing. The Asian Pacific Islander Teen Alliance of Chicago will also perform Japanese, Korean and Vietnamese dances. The band Hello Weekend will be the main headliner on the Saturday night.
Jazzin’ at the Shedd
The site of this annual series is what makes it so special. Where else can you stroll through an aquarium as you enjoy live jazz? It might just be the best way to see the Shedd Aquarium’s animal and marine life residents—with drink in hand, and bites at the ready. Jazzin’ at the Shedd takes place on Wednesday evenings from 5–10pm through August 27. Some of the featured bands this summer include Lake Effect (July 23), Rio Bamba (August 6), and the Victor Garcia Quintet (August 20).
Big Headliners
Chicago House Music Festival and Conference
House music was born in Chicago, and last year the city celebrated the genre’s 40th anniversary. This year, the beat and the love go on, with this popular celebration of house music taking place in Millennium Park on August 22 and 23. The free event features a lineup of the world’s top DJs as well as emerging talent. Underscoring the connection between the city and house music, this year the festival includes an industry conference, featuring panels full of house music icons and experts. Whether you go full student-mode and learn more about the history of house music, or you simply want to get your groove on, this is one weekend-long dance party you won’t want to miss.
Lollapalooza
Yes, we saved the best for last. Lollapalooza is the crown jewel of Chicago’s festival scene, taking over Grant Park with four electrifying days of music. This year, it’s all happening July 31 through August 3, and both 4-day and 1-day tickets are available. Every year, the world-renowned festival brings the biggest names in music to Chicago, and the 2025 Lollapalooza lineup is no exception—headliners include Olivia Rodrigo, Tyler, the Creator, Sabrina Carpenter, A$AP Rocky, Luke Combs, and Doechii. The good times extend beyond Grant Park, too, with Lollapalooza Aftershows taking place at music venues all over the city.
Make Arlo Your Base
As you can see, so many of these incredible festivals are happening practically on our doorstep. From Arlo Chicago’s location on N Michigan Avenue, it’s an easy walk to Millennium Park for the summer’s series of free concerts. It’s also super convenient to jump on the L and head to other neighborhoods to check out more live music. And whether you’re looking for a place to lay your head after a night out, a fun pre-game spot, or a post-show hang, Arlo Chicago has you covered. Check out our latest special offers to make planning your stay even easier and get set to experience the epic season that is Chicago in the summer.
