Top Outdoor Experiences in Chicago

A truly special event sail! ⛵✨ During the summer, every Wednesday and Saturday night, the Tall Ship Windy sails from Navy Pier for our guests to enjoy the spectacular night fireworks from the best seat in town. 🎆 Enjoy the amenities of the 148-foot, four-masted Schooner that is the official ship of the City of Chicago. 🚢 Sail from Navy Pier and take in the picturesque Chicago skyline. 🏙️ Experience one of the best summer fireworks displays in the nation aboard a world-class tall ship! 🎇 Then, get your history fix with a rousing rendition of traditional shipboard working songs against the backdrop of the brilliantly lit Chicago skyline. 🎶 This is a one-of-a-kind, uniquely Chicago experience! 🏴‍☠️ The Wednesday Fireworks Boat Tour departs promptly at 8:45 PM, and the Saturday tour departs at 9:15 PM. ⏰

Our popular 90-minute daytime river and lake tour, the Urban Adventure Cruise, delights family members of all ages with incredible views of Chicago's world-renowned architecture and stunning skyline. Lively, knowledgeable tour guides bring Chicago’s rich history to life with fun stories and interesting facts. Relax and unwind on a scenic tour of the city from the unique perspective of the Chicago River and Lake Michigan. Welcome aboard!

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. As a certified nonprofit, all ticket purchases directly support education efforts and community engagement projects. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building. Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including: John Hancock Center: An iconic skyscraper that defines the Chicago skyline. Wrigley Building: Known for its distinctive white facade and clock tower. As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities. Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.

Abraham Lincoln Park in Chicago is a peaceful neighborhood park offering a welcoming green space for relaxation and recreation. Located in the heart of the Lincoln Park community, this park is known for its open lawns, shaded areas, and a variety of amenities like playgrounds and walking paths, making it an ideal spot for families, joggers, and anyone seeking a break from city life. The park honors the legacy of Abraham Lincoln and provides a quiet, scenic environment for picnics, outdoor activities, or simply enjoying the outdoors in a tranquil urban setting. Its proximity to other Lincoln Park attractions adds to its charm, making it a favorite spot for locals.

The 606 is a unique urban trail and park system in Chicago, built along a former elevated rail line, providing a scenic route for walkers, runners, and cyclists. Officially known as the Bloomingdale Trail, this 2.7-mile-long greenway connects several neighborhoods, including Wicker Park, Bucktown, Logan Square, and Humboldt Park, offering a blend of art, nature, and community spaces. Lined with trees, native plants, and public art installations, The 606 provides a peaceful, elevated escape from the busy city streets below. It’s also a popular destination for community events, outdoor fitness classes, and seasonal activities. With its combination of recreational paths, vibrant green spaces, and a strong sense of community, The 606 is a beloved spot for both locals and visitors looking to enjoy Chicago’s outdoors.

Located in the heart of the Humboldt Park Community, Humboldt Park totals 197.26 acres and is home to a large, historic fieldhouse with a fitness center, two gymnasiums, and meeting rooms, as well as an inland beach and the historic lagoons and boat house. 

Rainbow Beach in Chicago is a lively destination along the shores of Lake Michigan, offering beautiful sandy shores 🌊 and stunning views. The beach is home to the Rainbow Beach Fieldhouse, which provides community programs and activities for all ages. Visitors can enjoy a variety of amenities, including a gym 🏋️‍♂️, picnic areas, and playgrounds, making it an ideal spot for families. Whether you’re swimming, sunbathing ☀️, or participating in community events 🎉, Rainbow Beach fosters an inclusive atmosphere where everyone can relax and have fun! 🏖️

The Garfield Park Conservatory, located on Chicago’s West Side, is one of the largest and most impressive botanical conservatories in the United States. Often referred to as "landscape art under glass", it spans over 2 acres of indoor gardens and 10 acres of outdoor space, offering a lush, tropical escape in the middle of the city. The conservatory houses a stunning variety of plants from around the world, with highlights like the Palm House, Fern Room, and seasonal flower shows. Visitors can explore everything from towering palms and exotic cacti to vibrant blooms and tranquil ponds. With its peaceful atmosphere and educational programs, the Garfield Park Conservatory is a perfect destination for nature lovers, families, and anyone looking to unwind in a serene, plant-filled environment.

Located in the Woodlawn community, Jackson Park totals 551.52 acres and features a gymnasium, three multi-purpose rooms, and a fitness center. Green features of the park include Wooded Island - which includes the Japanese Garden - Bobolink Meadows, cherry blossom trees around the Columbian Basin, and a vegetable garden. Outside, the park offers three harbors, 63rd St. Beach, basketball/tennis courts, multi-purpose fields, a golf course, a golf driving range, and an artificial turf field. Many of these spaces are available for rental including our multi-purpose fields, gymnasium, and multi-purpose clubrooms.