DAY 1 LOOP MORNING Start your day at the free Chicago Cultural Center , an ornate landmark completed in 1897. Book a free private group tour in advance to learn about the two spectacular Tiffany stained-glass domes — one of them is the world’s largest. See Chicago-themed exhibits in the galleries, and attend free events such as concerts, dance performances, and lectures. A few blocks south, tour the internationally acclaimed Art Institute of Chicago to see pieces ranging from a 12th-century statue of Buddha to an 1886 self-portrait of Vincent van Gogh and the iconic American Gothic painting by Grant Wood. The museum’s impressive collection includes the world’s largest number of Impressionist and Post-Impressionist works outside of the Louvre. IN CHICAGO 3 DAYS AFTERNOON Explore the Modern Wing, with paintings and sculptures from around the world. And be sure to take a photo with the new Route 66 marker across the street from the museum’s main entrance, which heralds the starting point of the historic Mother Road. Next door, visit Millennium Park , an oasis of lush gardens, cultural programs, and public artwork. Snap a group selfie in front of the shiny Cloud Gate sculpture (also known as “The Bean”), stroll through the all-seasons Lurie Garden , and splash through the multimedia Crown Fountain . Attend a concert at the architecturally impressive Jay Pritzker Pavilion and catch a free event like the Millennium Park Summer Music & Film Series . At the adjacent Maggie Daley Park , tackle the Climbing Wall , glide along the scenic Skating Ribbon , or play a game at City Mini Golf . Take a private backstage tour of the Auditorium Theatre , a National Historic Landmark on the downtown Roosevelt University campus. A gold-leaf ceiling adorns the impressive theatre, where major dance companies, Broadway musicals, and big-name musicians have staged shows for over 130 years. Walk north to the Chicago Riverwalk , home to popular attractions, cafes, and activities that get your group on the water in the heart of the city. Paddle a kayak through a canyon of skyscrapers during a guided Urban Kayaks tour. Board Chicago’s First Lady for the Chicago Architecture Center River Cruise that Take your group on a 72-hour bucket list tour of Chicago, experiencing local culture and must-see sights in our diverse neighborhoods while crisscrossing the city. showcases the city’s architectural treasures. Architecture tours are also offered by Wendella Tours & Cruises , Mercury Chicago’s Skyline Cruiseline , and Shoreline Sightseeing . Next, head to Skydeck Chicago atop Willis Tower (still affectionately called Sears Tower by the locals). Explore an interactive museum on the lower level that features Chicago-themed exhibits, from history to food and architecture. Then, take the high-speed elevator to the 103rd floor for panoramic views of the city and beyond. Step out onto The Ledge for a dizzying view of the city from a glass-floored balcony. EVENING Arrange for your group to spend the evening attending an exceptional performance. Choose from theatre, music, or the ballet. Broadway In Chicago offers some of the most popular touring musicals and plays throughout the year, along with premieres of pre-Broadway shows (which is unique to Chicago). Catch a show at one of five historic downtown theatres. Hear classical music during a Chicago Symphony Orchestra performance at Symphony Center. The Grammy Award-winning orchestra collaborates with some of the best conductors and guest artists on the international music scene. Opera aficionados will want to attend a beautifully staged Lyric Opera of Chicago performance within its stunning art deco theatre. Don’t miss the opportunity to see one of the world’s premier dance companies. The Joffrey Ballet presents classical and contemporary ballets at the Lyric Opera House. Maggie Dale y P ark Cl im bi n g all W SCAN HERE TO EXPLORE MORE GROUP ITINERARIES. 3
Chicago Travel Professionals Guide 2025: Page 3
