Chicago is one of the country’s great summer cities, with a lineup of outdoor festivals, iconic sporting events, and world-class music that draws crowds from across the Midwest and beyond. Whether you’re visiting from out of town or rounding up a group of friends, coworkers, or family, getting to and from Chicago’s biggest summer events is easier with professional group transportation. Aries Charter Transportation offers a wide range of charter vehicles in Chicago — from luxury Motor Coaches and Minibuses to classic Trolleys, Sprinters, Sedans, Limos, and SUVs — making it simple to keep your group together and on schedule.
Here’s a look at some of the events filling Chicago’s summer calendar in 2025, and why booking a private event charter is the smartest move for your group.
The summer season kicks off in July with the Windy City Smokeout, held July 10–13 in the parking lot of the United Center. Known for combining some of the country’s top country music acts with award-winning barbecue vendors and craft beer, this event continues to grow year after year. With large crowds, limited parking, and multiple entry points, chartering a Minibus or Sprinter for your group ensures you’ll be dropped off and picked up close to the main gates, no rideshare surge pricing or long walks required.
Chicago’s biggest music festival, Lollapalooza, returns to Grant Park from July 31 to August 3, 2025. Drawing more than 100,000 attendees a day, it’s one of the largest multi-day festivals in the U.S. With road closures and heavy foot traffic around Michigan Avenue and Columbus Drive, having a pre-arranged charter service simplifies transportation logistics for larger groups. Whether you’re traveling with a handful of friends or a full company outing, Aries can arrange everything from SUVs to full-size Motor Coaches.
In mid-August, the skies above North Avenue Beach come alive with the Chicago Air & Water Show, scheduled for August 16–17. The free event attracts thousands to the lakefront for jet team demonstrations, parachute jumps, and water stunts. Large group outings to this event benefit from private transportation, avoiding crowded parking lots and allowing you to set up your picnic spot without worrying about where to leave your vehicle.
Baseball season is in full swing through the summer, with both the Chicago Cubs at Wrigley Field and the Chicago White Sox at Guaranteed Rate Field offering packed home stands. Chartering a Trolley or Minibus to either ballpark means your group can tailgate together, skip the parking hassle, and enjoy the game without worrying about traffic on the way home.
August also marks the start of football season, with the Chicago Bears’ Pre-Season Opener taking place at Soldier Field. Group transportation for Bears games has long been one of the most popular services Aries offers, with options like Sprinters and Motor Coaches perfect for bringing fans to the stadium and back with ease.
Rounding out the season, the Chicago Jazz Festival returns Labor Day weekend, August 28–31, in Millennium Park. It’s one of the city’s longest-running music traditions, offering free performances from local talent and international headliners. Group transportation to the Jazz Festival allows you to enjoy multiple sets across Grant Park and Pritzker Pavilion without juggling public transit or rideshare queues.
To book your summer event transportation, visit Aries Charter Transportation and explore our full fleet options or request a custom quote. Chicago summers were made for live music, sports, and lakefront festivals — and Aries is here to help you get to every one of them.