Every summer, someone hands you a Chicago bucket list full of things you either already did or can’t do until next year. This one is different. Whether you’re visiting for the first time or you’re a regular who wants to go deeper into what makes summer in Chicago so addictive, this guide covers the Chicago summer activities worth actually putting on your calendar, all easy to reach from Arlo Chicago on North Michigan Avenue.
Go to Lollapalooza
If you’re in Chicago at the end of July, there’s one event that defines the city’s summer energy better than anything else: Lollapalooza. The legendary festival returns to Grant Park from July 30 through August 2, spreading across multiple stages with a lineup that spans rock, hip-hop, electronic, and everything in between.
Grant Park sits about a 15-minute walk from Arlo Chicago, making it one of the most convenient festival locations imaginable. Buy your tickets in advance; single-day and four-day passes both sell out quickly.
Catch Free Music and Movies at Millennium Park
You don’t need to spend a dime to enjoy great entertainment this summer. The Millennium Park Summer Music Series brings free concerts to the Jay Pritzker Pavilion on Mondays and Thursdays through early August — and on Tuesday nights, the lawn turns into an outdoor cinema for the free Summer Film Series, running most Tuesdays through August 18 (no screening July 21).
The Pavilion’s iconic bandshell sits about a 5-minute walk from Arlo Chicago’s front door; pack a blanket, grab food from a nearby spot on Michigan Avenue, and settle in for one of the most distinctly Chicago summer experiences you can have.
Watch the Chicago Air and Water Show
Few things to do in Chicago in the summer rival the sheer spectacle of the Chicago Air and Water Show. The show takes place at North Avenue Beach on August 15 and 16, with a rehearsal on August 14.
Fighter jets, aerial acrobats, and military demonstrations fill the sky above Lake Michigan in a display that draws more than a million spectators. North Avenue Beach sits about three miles from Arlo Chicago; grab a 13-minute rideshare to get there early and claim a good spot on the sand before the crowds lock in.
Explore the Chicago Riverwalk
The Chicago Riverwalk runs along the south bank of the Chicago River through the heart of the city, lined with restaurants, bars, kayak rentals, and some of the best architectural views in the world.
It’s one of those unique activities in Chicago that feels equally at home on a lazy afternoon or a festive summer evening. Arlo Chicago sits about a 7-minute walk from the Riverwalk’s Michigan Avenue access point; stroll west along the water, grab a drink at one of the outdoor patios, and let the city’s skyline do its thing.
Dance at Chicago SummerDance
Chicago SummerDance runs throughout the summer, bringing free dance lessons and live music to the Spirit of Music Garden in Grant Park and pop-up locations across the city. The format is brilliantly simple: instructors teach a style, salsa, swing, West African, cumbia, and then a live band plays while everyone dances under the open sky.
It’s one of the most joyful and underrated summer in Chicago experiences you’ll find, and it costs absolutely nothing. Grant Park is just a 12-minute walk from Arlo Chicago, so it’s an easy experience to have.
Head Out to Navy Pier
Navy Pier delivers a full summer afternoon all on its own. The 50-acre pier stretches into Lake Michigan and packs in dining, a Ferris wheel, boat tours, live entertainment, and sweeping views of the city’s skyline from the water.
Navy Pier sits about 1.5 miles from Arlo Chicago, about a 30-minute walk if the weather cooperates, or a quick 5-minute rideshare if you’d rather save your energy for the pier itself. Wednesday and Saturday evening fireworks run throughout the summer season, so time your visit accordingly.
End Summer with the Chicago House Music Festival
The Chicago House Music Festival takes over the Chicago Cultural Center and Millennium Park from August 27 through 30, celebrating the genre that Chicago gave to the world. Four days of performances, DJ sets, and panels honor house music’s deep roots in the city, all within easy walking distance of Arlo Chicago. It’s a fitting way to close out the season, loud, soulful, and unmistakably Chicago.
Make Arlo Chicago Your Base
The best Chicago summer itinerary starts with the right place to stay, and Arlo Chicago on North Michigan Avenue puts you within walking distance of Millennium Park, Grant Park, the Riverwalk, and some of the city’s best neighborhoods.
Book your stay at Arlo Chicago and spend your summer the way it was meant to be spent, out in the city, doing all of it.
