Top 4 Can’t-Miss Chicago Events This Summer
- Ian Malanes
- Jun 30
- 2 min read
Chicago is a city that truly shines during the summer months. With festivals, music, food, and fireworks lighting up the skyline, there’s always something exciting happening, especially along Lake Michigan.
Aboard the Nebula, you can enjoy these iconic events from a unique vantage point: the water. Whether you're watching fireworks over Navy Pier or soaking in the energy of Lollapalooza from the lake, a sailing charter adds an unforgettable twist to your event experience.
Here are four must-attend summer events in Chicago, and how to make them even more memorable with a private yacht charter aboard the Nebula.

🎟️ 1. Lollapalooza – July
Held annually at Grant Park, Lollapalooza brings together top-tier musical acts across genres, rock, pop, EDM, hip-hop, and more. It’s one of the most anticipated music festivals of the year.
While thousands pack into the park for live performances, imagine enjoying the festival from the comfort of the Nebula, anchored just offshore. You’ll hear the beats, see the lights, and enjoy a peaceful escape from the crowds — all while sipping drinks and soaking in the atmosphere.
After the final encore, unwind with a sunset sail back to the harbor for the perfect end to a high-energy day.
🪂 2. Chicago Air & Water Show – August
This free, two-day event showcases some of the most thrilling aerial stunts in the world. Held at North Avenue Beach, the show features military jets, skydivers, aerobatic pilots, and precision flying teams, such as the U.S. Navy Blue Angels.
Watching from land is impressive, but watching from the Nebula is unforgettable. From the deck of our sailboat, you’ll have a front-row seat to the action, with unobstructed views of planes soaring overhead and diving low over the lake.
It’s a breathtaking display of skill and power — best enjoyed with a cold drink in hand and the breeze in your hair.
🍽️ 3. Taste of Chicago – July
Calling all foodies! The Taste of Chicago is the city's largest outdoor food festival, featuring dishes from top local restaurants and chefs. From deep-dish pizza to gourmet street tacos, it’s a celebration of Chicago cuisine.
After a full day of sampling delicious bites, cool off with a scenic sail on Lake Michigan. A post-Taste cruise aboard the Nebula provides a relaxed way to savor and reflect on the city's flavors, all while enjoying panoramic views of the skyline.
4. Chicago Blues Festival – June
As the largest free blues festival in the world, the Chicago Blues Festival draws artists and fans from around the globe. Held at Grant Park, the festival celebrates the genre that helped shape Chicago’s cultural identity.
Sail past the festival grounds on the Nebula and enjoy the soulful sounds drifting across the lake. It’s a unique way to take in the music without the crowd, while still feeling the rhythm of the city.
Whether you're a lifelong blues fan or new to the scene, this festival pairs beautifully with a relaxing evening sail.
Comments