Chicago Travel Professionals Guide - 2025

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.

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.

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.

AFTERNOON

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 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.

MORNING

For bird’s-eye views, head to 360 CHICAGO on the 94th floor of the former John Hancock Center. Visitors can step onto the TILT platform that angles over the edge of the observation deck 1,030 feet (.31 kilometers) above The Magnificent Mile.

Afterward, head to the nearby Museum of Contemporary Art to see revered works dating from the 1920s to the present. Arrange for your group to go on a private, customized tour. You can also attend an informative art talk or cultural program.

AFTERNOON

Iconic Navy Pier offers a variety of attractions, activities, and events year-round, surrounded by breathtaking Lake Michigan views. Take off on a simulated flight for an immersive adventure that soars high above some of Chicago's most magnificent sights with Flyover. Board a leisurely City Cruises Chicago brunch or lunch cruise. Or opt for the Chicago Seadog Extreme Thrill Ride speedboat tour. Experience 360-degree city views on the soaring Centennial Wheel or ride the old-fashioned carousel in Pier Park. Then, take a relaxing stroll and watch free cultural performances at Polk Bros Park.

End the afternoon on a sweet note at the Museum of Ice Cream. Discover how ice cream is made, play ice cream-themed games at 14 different installations, and eat as many ice cream treats as you like. Group bookings are available.

EVENING

Tonight, more exciting entertainment is on tap for your group. Choose from a concert, comedy, or theatre.

Attend a concert at The Salt Shed in a historic setting. The venue features both indoor and outdoor events on the site of the former Morton Salt complex, located on the North Branch of the Chicago River.

Laughs abound at The Second City, known as the birthplace of improv. Catch tomorrow’s comedy stars in unscripted, interactive shows in the Old Town neighborhood. Famous alumni include Amy Poehler, Tina Fey, and Bill Murray.

The award-winning Steppenwolf Theatre Company, featuring an ensemble cast, offers critically acclaimed productions in Lincoln Park. Actors, directors, and playwrights contribute their expertise for small and large shows in three theatres.

See the Blue Man Group, a trio of hilarious bald men painted blue who entertain with a unique brand of performance art at the Briar Street Theatre. It’s a multisensory experience that combines a live band, dazzling lights, and creative technology.

MORNING

Explore a storied Chicago neighborhood this morning. Choose either leafy Lincoln Park or collegiate Hyde Park as your destination.

LINCOLN PARK

Get close to wildlife on a self-guided tour at the Lincoln Park Zoo, where admission is always free. Sign up for the Malott Family Penguin Encounter, which includes a behind-the-scenes tour and a chance to be greeted by the African penguins in their habitat.

See nature-inspired exhibits at the nearby Peggy Notebaert Nature Museum, which features outdoor walking trails. You’ll be surrounded by over 1,000 free-flying butterflies in the Judy Istock Butterfly Haven greenhouse.

Delve into local history at the Chicago History Museum. Groups can explore fascinating artifacts, interactive displays, and exhibits with themes such as the Great Chicago Fire and the 1893 Chicago World’s Fair. Join a behind-the-scenes tour of the museum or take a walking tour and visit area neighborhoods.

HYDE PARK

Discover two of the city’s leading museums in Hyde Park. The massive Griffin Museum of Science and Industry is home to hundreds of interactive exhibits that include an actual World War II U-505 German submarine that you can walk through, plus the five-story wraparound Giant Dome Theater. At The DuSable Black History Museum and Education Center, view African American artworks and historical exhibits, and attend a lecture or workshop focused on diversity.

Explore the grounds of the historic, ivy-covered University of Chicago. See fascinating collections at the Institute for the Study of Ancient Cultures Museum. Take a guided group tour of the works at the Smart Museum of Art that aim to spark conversation. See the best example of Frank Lloyd Wright’s Prairie-style architecture on a docent-led tour of the 1910 Frederick C. Robie House, a National Historic Landmark and UNESCO World Heritage Site. It’s flush with modernism details such as iridescent leaded glass windows, wood beams, balconies, and impeccable landscaping.

Former President Barack Obama chose Chicago as the home of his Obama Presidential Center (opening in spring 2026) and its Home Court athletic and event center, opening in late 2025.

Plans for the Jackson Park campus include a library, museum, John Lewis Plaza, and The Forum Building. Public gathering spaces include the Ann Dunham Water Garden honoring Obama’s mother, the Hadiya Pendleton Winter Garden, and the Elie Wiesel Auditorium.

AFTERNOON

For your afternoon adventure, choose to explore either the Latino culture of Pilsen or the Asian history of Chicago’s Chinatown.

PILSEN

In this culturally rich neighborhood, see outstanding artwork and exhibits celebrating Mexican heritage and history at the free National Museum of Mexican Art. Attend cultural events and programs highlighting visual and performing arts, including dance, music, theatre, and literature.

View the vivid murals along lively 16th Street and nearby blocks at your own pace using A Guide to Pilen’s Murals, available on the National Museum of Mexican Art’s website. While strolling the neighborhood, stop by one of the authentic taquerias or bakeries. Next, peruse the galleries on South Halsted Street in the Chicago Arts District.

End the afternoon at the Pilsen Arts & Community House, a nonprofit gallery curating local exhibitions and offering pop-up shows, artist talks, and art instruction. Its mission is to nurture creativity, culture, and community. Guided mural tours of the neighborhood are offered.

CHINATOWN

In Chinatown, make your first stop the Chinese American Museum of Chicago and delve into the neighborhood’s history with exhibits that range from art to military heroes, food, and storytelling. Book your group visit for a customized introduction to rich Chinese culture.

Pause for photos at the iconic Chinatown Gate, then shop for souvenirs in the colorful boutiques or stop for a sweet from an authentic Chinese bakery or boba tea shop along Wentworth Avenue. In Chinatown Square, discover eateries offering dim sum and an array of Chinese cuisine. Look for the 12 bronze sculptures on the plaza that represent the animal signs of the Chinese zodiac.

Along the Chicago River on a former railyard site, Ping Tom Memorial Park is a great place to relax, stroll waterfront paths, and enjoy views of the city skyline before your afternoon in Chinatown ends. You can also catch a seasonal Chicago Water Taxi here, an inexpensive way to whisk your group to and from downtown.

EVENING

Choices abound for your last night of entertainment in Chicago. Make it a special evening by visiting one of these venues.

A Rock & Roll Hall of Fame guitarist is behind the magic that happens Wednesday through Sunday nights at Buddy Guy’s Legends in the South Loop. Buy tickets in advance for your group to hear live blues music by some of the genre’s biggest artists while enjoying Southern fare like Louisiana-style gumbo. Be sure to check out the blues memorabilia that adorns the walls. Guy himself performs every January.

In Lincoln Park, see performances on two stages at Kingston Mines, the oldest continuously operating blues club in Chicago. Some of the brightest stars in the business perform here Thursday through Sunday nights. Arrive early for the best seating. Doc’s Kitchen is open nightly, serving pub fare in addition to Southern specialties like catfish and pecan pie.

Groove to jazz and big band beats in Uptown at the historic Green Mill, featuring live music every night. Open since 1907, it’s said to be the country’s oldest jazz club and a former haunt of Prohibition Era gangsters. Your group can hit the dance floor when bands play dance music on Tuesday and Thursday evenings. The popular cocktail lounge accepts cash only and doesn’t take reservations.

In Pilsen, catch a concert at Thalia Hall, where shows range from indie rock bands to singer-songwriters and DJs. The turn-of-the-century landmark’s architectural inspiration came from the Prague Opera House. Head down to the retro basement for a drink at Punch House or check out Tack Room, a cozy cocktail bar with a pianist and patio seating. Thalia Hall’s restaurant, Mariscos San Pedro, specializes in Mexican seafood.

For artisanal cocktails made by expert mixologists, stop by The Violet Hour in Wicker Park. The cocktail menu changes with the season. There are three salons with candlelit tables, but the venue offers private areas for larger parties. For a fun group activity, book a dinner and cocktail-making class.

SCAN HERE TO EXPLORE MORE GROUP ITINERARIES.