Memorial Day weekend in Chicago signals the unofficial start to summer and 2025 is shaping up to be packed with parades, festivals, markets, and outdoor fun. With so many events happening across the city — and traffic, parking, and crowds to deal with — it’s the perfect time to plan ahead with professional group transportation. Whether you’re organizing a family outing, a group of friends, or a company event, Aries Charter Transportation has you covered with luxury Motor Coaches, Minibuses, Trolleys, Sprinters, Sedans, Limos, and SUVs to keep your plans running smoothly.
Here’s a look at some of the standout Memorial Day events happening in Chicago this year — and why booking a charter service is the easiest way to get your group around town.
2025 Memorial Day Events in Chicago
Memorial Day Parades
The city’s biggest and oldest Memorial Day event steps off downtown along State Street. Expect road closures, packed sidewalks, and big crowds honoring those who served. Nearby, the McKinley Park Memorial Day Parade offers a more neighborhood-focused experience, while the River Forest Memorial Day Parade brings out families for a patriotic morning. Booking a Sprinter or Minibus ensures your group arrives together, on time, and hassle-free.
Belmont-Sheffield Music Festival
This lively street fest in Lakeview features live bands, food vendors, and outdoor patios. It’s a popular way for locals to kick off summer with friends and neighbors. Avoid the parking nightmare with Aries Charter Transportation for your crew.
Mayfestiversary
Hosted by Begyle Brewing and Dovetail Brewery in Ravenswood, Mayfestiversary blends craft beer, live music, and food trucks for a laid-back, family-friendly vibe. A luxury Motor Coach or Minibus is ideal for groups who want to safely enjoy the festivities without worrying about parking or rideshares.
Sueños Music Festival
This two-day reggaeton and Latin music festival at Grant Park draws huge crowds and big-name artists. With streets around the park closed to traffic, a professional charter service can handle drop-offs and pickups without the stress of navigating the crowds.
Mole de Mayo Festival
Pilsen’s popular street festival celebrates Mexican culture with mole-tasting competitions, live performances, and local vendors. Getting a Sprinter or SUV for your group makes visiting this vibrant neighborhood festival far easier than dealing with local parking.
Randolph Street Market Festival
Chicago’s favorite antique and vintage market returns Memorial Day weekend with dozens of vendors, food stalls, and music. A luxury Coach or Minibus can shuttle shoppers comfortably while leaving plenty of room for finds.
Baseball Games & Navy Pier Fireworks
Both the Cubs and White Sox are in town Memorial Day weekend, with post-game fireworks and festivities. The White Sox have a three-game home series against the Texas Rangers from May 23-25. The Cubs will face off against the Colorado Rockies on May 26. And speaking of fireworks, Navy Pier kicks off its summer firework series Saturday night. Coordinating rides for a group? Skip multiple rideshares and go with a Sedan, Limo, or Minibus to get your whole group to the stadium or pier together.
Memorial Day weekend in Chicago means heavy traffic, packed parking lots, and busy streets. Booking a charter service with Aries Charter Transportation keeps your group organized and lets you focus on enjoying the holiday weekend. Whether you need a Motor Coach for a full-day outing, a Minibus for a festival crew, or a Trolley for a unique group ride, we’ll get you there comfortably and safely.