Chicago comes alive in August and September with festivals, concerts, sports, and cultural celebrations across the city. Whether you’re heading downtown for a major music act, meeting friends at a neighborhood fest, or making it to the first open-water swim in the Chicago River in nearly a century, the right transportation can make the day run more smoothly.
Here’s a look at what’s happening in the city during these two months, along with practical tips for getting there with Galaxy’s fleet of sedans, SUVs, and limousines.
Live on the Lake! and Navy Pier’s Summer Art Programs
Live on the Lake! runs through September 1, 2025, with free weekend concerts at Navy Pier. Performances range from local jazz and blues acts to indie rock and Latin rhythms.
Navy Pier is also hosting rotating art installations, including Artists at the Pier and Escaramuza, the Poetics of Home. These exhibits add a creative layer to a visit, giving you a mix of live entertainment and cultural experiences in one trip.
Getting there: Traffic near Navy Pier can be slow on weekends, and parking fills quickly. Booking in advance through our reservations page ensures your drop-off is right at the entrance, with pickup timed after the show ends.
The Chainsmokers Concert and Great American Lobster Fest
Two back-to-back events make Navy Pier a focal point in mid-August:
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The Chainsmokers perform on August 16. This Grammy-winning duo is known for high-energy shows and draws large crowds.
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The Great American Lobster Fest follows on August 17, offering fresh seafood, live music, and harbor views.
Chicago Cubs Doubleheader at Wrigley Field
On August 18, the Cubs will play a doubleheader against the Brewers at Wrigley Field. Day-night doubleheaders can be long, so having a pre-arranged ride is ideal if you plan to stay for both games or head out between them.
Taste of Polonia
Taste of Polonia runs from August 29 to September 1, 2025, in Jefferson Park. The festival is one of the largest Polish cultural celebrations in the country, featuring traditional food, music, dance, and family activities.
German-American Fest
From September 5–7, the German-American Fest transforms Lincoln Square into a celebration of German culture with food stands, beer tents, live bands, and the Von Steuben Parade.
Chicago River Swim
The Chicago River Swim on September 21, 2025, is making history as the first open-water swim in the river in 98 years. With about 500 swimmers starting at the Dearborn Street Bridge and finishing at the Clark Street Bridge, this is as much a spectator event as it is an athletic competition.
Planning Tips for Late-Summer Events
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Book early: Popular weekends fill fast for limousines and larger vehicles.
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Know your schedule: Share your itinerary so pickups and drop-offs can be planned efficiently.
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Consider group travel: Sharing a larger vehicle can be more economical.
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Plan for traffic: Road closures are common during festivals and parades.
Reserve Your Ride
If you already have tickets to any of these events, now is the time to secure your transportation. Visit our reservations page to choose your vehicle and pickup times.