Take your student group on a fascinating journey through Chicago by foot, bike, and boat. They’ll discover the city’s history, visit world-famous landmarks and museums, watch entertaining theatre and improv comedy performances, and learn some fun facts along the way.
Day 1
Morning
Start off the day with a thrilling visit to The Ledge at Skydeck Chicago. Students will step onto glass-floored balconies that jut out 4.3 feet (1.3 meters) from the Willis Tower, offering sweeping views of the Chicago skyline, Lake Michigan, and four states. Before your group begins their trip up the tower, visit Skydeck Chicago’s city-themed museum on the first floor. Hands-on exhibits teach students about historic moments and landmarks, take them on a video tour of Chicago’s world-renowned architecture, and introduce them to some of Chicago’s famous foods (think pizza and hot dogs!).
Fun fact: Located on the 103rd floor of the Willis Tower, Skydeck Chicago is the highest observation deck in the country at 1,353 feet (412 meters) above the ground.
Afterward, head to Color Factory Chicago, also located in the Willis Tower. At the immersive art attraction, learning focuses on exploring color to engage the senses, art appreciation, and collaborations with artists. Students will experience 14 interactive exhibits, including diving into a 2,600-square-foot ball pit or discovering their own colorful birthday horoscope. Be sure to take group photos in the vibrant confetti room.
Afternoon
Students will be awestruck viewing Impressionist paintings at the Art Institute of Chicago — it’s the largest collection outside of Paris — in addition to amazing works by the likes of Van Gogh, Dali, Picasso, and many more. Take your group to the Ryan Learning Center, where they can make art and collaborate with others. Or visit The Trott Gallery for an interactive session on how conservators use art and science to care for the museum’s artworks.
Fun fact: The Art Institute of Chicago’s collection of 300,000 pieces includes paintings by influential American artist Georgia O’Keeffe, a former student at the School of the Art Institute of Chicago, who had her first retrospective there in 1943 when she was in her 50s.
Stroll through magnificent Millennium Park, stopping to admire attractions like the splashy Crown Fountain, architecturally impressive Jay Pritzker Pavilion that hosts free summer concerts, and the reflective Cloud Gate sculpture (affectionately known as “The Bean”). Go on a tour of the blooming Lurie Garden — just one of the beautiful gardens of Millennium Park — and arrange for a volunteer to lead a private tour focusing on native plants and urban habitats.
Fun fact: Millennium Park acts as a 24.5-acre rooftop garden, covering an underground parking garage and commuter train lines.
You can request that some of Chicago’s iconic sights be included on a private group bicycle tour with Bobby’s Bike Hike Chicago.
Evening
Broadway In Chicago offers discounted group tickets for acclaimed touring shows on five stages throughout the Downtown Theatre District — add a post-show Q&A or a theatre tour as a bonus for your group. It’s a special experience to see a new show that’s bound for Broadway — productions like Spamalot, The Addams Family, and Kinky Boots were all onstage here first.
Or, take your students to watch laugh-out-loud antics at the interactive, high-energy ComedySportz. They’ll get a chance to vote for which team wins the evening’s improv competition. Shows emphasize the importance of being a good sport, keeping it fun for everyone. If a performer or audience member uses foul language or references something off-color, the referee calls an Out of Bounds penalty. Another comedy option is the legendary iO Theater, known for improv, sketch, and stand-up comedy performances. It has been a training ground for famous comedians like Tina Fey, Amy Pohler, and Stephen Colbert. See live shows on four stages five nights a week.
Day 2
Morning
Start the day along the Chicago Riverwalk. Learn about the city’s history, architectural treasures, and visions of the future by viewing exhibits or taking part in a workshop at the Chicago Architecture Center.
Fun fact: The Chicago Architecture Center offers more than 85 tours led by expert guides, exploring architectural gems on foot, by boat, and even aboard a CTA train.
Continue your group’s architecture lesson on the water by scheduling an educational river boat cruise with one of the dockside tour operators — Chicago’s First Lady Cruises, Shoreline Sightseeing, or Wendella Tours & Cruises — to take in the historic skyscrapers and landmarks.
Afternoon
Spend the afternoon at the Museum Campus, a 57-acre lakefront park that includes three internationally lauded institutions — the Field Museum, Shedd Aquarium, and Adler Planetarium. Explore ancient artifacts and towering dinosaurs at the Field, where groups can go on behind-the-scenes tours and reserve designated times to view special ticketed exhibitions. Encounter marine life from around the world at the Shedd, enhanced with the 4D Experience, a movie about penguins, sharks, and octopuses featuring high-tech special effects. Repeat visitors will be amazed at some of the transformations already unveiled as part of a current major renovation that’s planned to be completed by 2027 — recently opened is the Wonder of Water exhibit showcasing saltwater and freshwater ecosystems. While discovering the far corners of space at the Adler, add a 30-minute sky show in one of the domed theaters.
Fun fact: Founded in 1930, the Adler Planetarium was the first planetarium in the Western Hemisphere.
Evening
Return to the Chicago Riverwalk at night to experience Art on THE MART. Join the crowd of spectators who gather to see the fusion of art and technology that transforms the riverfront into a larger-than-life outdoor gallery. The free experience features captivating digital projections accompanied by music.
Fun fact: Art on THE MART is the world’s largest permanent digital art platform — the size of two football fields — showcasing moving art images on the exterior of the former Merchandise Mart every night, from April to December.
Day 3
Morning
For a glimpse into the city’s storied past, the Chicago History Museum in Lincoln Park offers fascinating exhibits, artifacts, and interactive displays. Discover interesting details about the city’s founding, the Great Chicago Fire, politics, and cultural innovation. See Abraham Lincoln’s belongings, a vintage ‘L’ train car, sports memorabilia, and lots more.
Also in Lincoln Park, the Peggy Notebaert Nature Museum is dedicated to nature, science, and conservation. Begin your group’s visit outdoors on the Deb Lahey Nature Trails, then head inside to experience hands-on exhibits and hundreds of free-flying butterflies in the Judy Istock Butterfly Haven.
Afternoon
Introduce your students to wildlife and conservation concepts during an outing at Lincoln Park Zoo, where admission is always free. Included in the zoo’s resident 200 species are lions, giraffes, pandas, penguins, birds, and reptiles. Sign up for a 55-minute Zoo Explorers session that focuses on inquiry-based animal investigations by zoo scientists. Lincoln Park Zoo emphasizes animal welfare, conservation research, and education in its six science centers.
Fun fact: In 1878 it was decided that no admission fee would be charged to visit Lincoln Park Zoo, today making it the longest-running free zoo in the United States.
Or spend the afternoon at Navy Pier, filled with an array of activities and attractions. Take a spin on the 200-foot-tall (61-meters-tall) Centennial Wheel for spectacular city and Lake Michigan views. The ride is a tribute to the original illuminated Ferris Wheel that debuted at the 1893 World’s Columbian Exposition in Chicago and attracted millions of visitors to marvel at the sight. At Flyover, embark on a nine-minute simulated flight above Chicago landmarks, complete with sensations that include wind, mist, and scents.
Fun fact: The Centennial Wheel features a VIP gondola with plush seats and a glass bottom for even more amazing views.
Leave room for a sweet adventure at the Museum of Ice Cream on North Michigan Avenue. The interactive experience features themed rooms like the sprinkle pool, unlimited ice cream samples, and whimsical photo opportunities.
Evening
Return to Navy Pier to catch a play at the Tony Award-winning Chicago Shakespeare Theater. Ask about advance study resources to prepare students before the show. Arrange for your group to attend a Pre-Amble, where a scholar gives a pre-performance lecture, or a post-show discussion with the actors. Further customize your visit with help from the theatre’s education department.
Fun fact: The Chicago Shakespeare Theater began as a group of 19 artists performing on the rooftop of Lincoln Park’s Red Lion Pub in 1986.
Or, let your students work together to solve clues and beat the clock at The Escape Game Chicago in River North. Choose from five different themes that range from Mission: Mars to The Heist.
There are also plenty of free things to do year-round. Check out Chicago’s calendar of events to help plan your group trip.
