Chicago for Groups

Chicago rises with confidence, its soaring towers mirrored in the river that runs through it, the “L” trains clattering overhead, and 77 distinct neighborhoods pulsing with personality. Framed by the vastness of Lake Michigan, this Midwestern city draws both first-timers and longtime fans with art, architecture, history, sports, and moments that genuinely impress. For tour operators building multiday itineraries, Chicago delivers on accessibility, flexibility, and adventure that keeps groups engaged from arrival to departure.

That promise hasn’t gone unnoticed. Recently named Condé Nast Traveler’s Best Big City in the U.S. for the ninth consecutive year, Chicago has earned an unprecedented distinction that reflects what group travelers have long known.

“This is a city that’s never done and never outdone when it comes to delivering extraordinary visitor experiences,” says Kristen Reynolds, Choose Chicago president & CEO. “With easy and ample access from anywhere in the U.S., world-class cultural institutions, an endless array of culinary experiences, and iconic architecture, we are the destination that will wow your groups and keep them coming back for years to come.”

Big Bus Tours offers special rates for groups who wish to charter a bus to enjoy the city. The open-air experience on the top deck is special to travelers—a high percentage are on an open-top bus for the very first time.

The Chicago skyline and riverfront form a striking display of architecture, culture, and city life—an unmistakable signature of the Windy City.

The Chicago Architecture Center serves as an educational hub and a natural launchpad for many planners. Here, the skyline is a living cultural artifact that helps groups understand why Chicago looks the way it does.

CAC’s knowledgeable docents tailor experiences to a wide range of ages and interests, giving groups a framework that makes the city’s architecture more meaningful once they step outside.

Groups standing on The Ledge at the Willis Tower’s 103rd floor can see a 360-degree view of a city that continues to grow and inspire.

“At 360 CHICAGO, we use our vantage point to tell a story that goes beyond just Chicago hot dogs and deep-dish pizza,” says Jim Vozzella, senior sales manager at 360 Chicago.

No group should leave Chicago without taking an Architecture River Cruise. Tour guides explain how Chicago’s buildings, infrastructure projects, and river redesign transformed it into a modern urban masterpiece.

One of the most exciting highlights for 2026 is Navy Pier’s role in the 100th anniversary of Route 66. Established in 1926 and stretching nearly 2,500 miles from Chicago to Santa Monica, Route 66 holds a special place in American travel history.

“Navy Pier connects visitors directly to Chicago’s waterways while offering planners exceptional flexibility.” —Elizabeth Halajian, Senior Vice President of Advancement, Navy Pier

The man-eating lions of Tsavo are two of the Field Museum’s most famous residents—and also the most infamous.

At more than 40 feet long and 13 feet tall at the hip, SUE is physically the largest and most complete Tyrannosaurus rex specimen ever found.

The Second City offers groups a shared cultural experience rooted in Chicago’s humor, grit, and heart.

Some of the oldest penguins at Shedd Aquarium are just a few years shy of 40. That’s over three times the age we might expect them to live in the wild.

Tours of Wrigley Field are offered throughout the year and work well for groups of any size, even when the Cubs are not in season.

The Obama Presidential Center offers specially curated group tours that provide a unique perspective into the stories that shape the Center.

Why Chicago Works for Groups

Chicago’s appeal for groups starts with accessibility and extends through every stage of planning and execution. “Chicago is built for groups of all sizes and all seasons,” says Lisa Nucci, chief marketing officer at Choose Chicago. “With two major airports, a walkable downtown, and attractions with a wide range of price points, planners can design itineraries that are both efficient and deeply engaging.”

As the official destination marketing bureau for the city, Choose Chicago supports planners with motorcoach maps and parking guidance, large hotel inventory, seasonal programming, mobile-guided tours, group ticketing, and bundled experiences.

Nucci notes that Chicago’s balance of iconic attractions and authentic neighborhood experiences reflect the city’s evolution as a group destination. “The Architecture River Cruise gives groups the views, the history, and the inspiration for what to explore next,” she says, citing cultural districts such as Hyde Park, Bronzeville, Pilsen, and Chinatown, along with continued growth in the West Loop, Fulton Market, and the South Side. Bally’s Chicago casino resort and a 21-and-over magic venue on the Magnificent Mile, set to open in 2026, reflect the city’s evolution as a group destination.

As itineraries take shape, Chicago unfolds through three lenses: sky, sea, and story, guiding groups from skyline views to waterfront moments and into the stories that anchor every stop.

Start With the Big Picture

For first-time groups, Big Bus Tours serve as a smart entry point—a flexible, hop-on, hop-off way to see the city at a comfortable pace.

“Big Bus Tours are the perfect first introduction to any city, and Chicago is no exception,” says John Curran, general manager of Big Bus Tours. “It’s the easiest, most engaging way for groups to see several of Chicago’s most iconic destinations while learning the stories behind them at the same time.”

Groups often charter buses at special rates, allowing Big Bus to function not only as sightseeing but also as creative transportation between attractions. This approach improves itinerary flow while reducing stress related to navigation and timing. 

New for 2026, Big Bus has enhanced its recorded audio commentary, now offered in both English and Spanish, and expanded the experience with complimentary self-guided walking tours included with select tickets. These tours highlight Loop architecture, the Riverwalk, public art, and Millennium Park, allowing groups to extend their exploration beyond the bus. Seasonal offerings such as the Sunset Live Tour—available mid-May through mid-October—take guests through neighborhoods including the Gold Coast and Lincoln Park, guided live during Chicago’s golden hour.

“My best advice for passengers is simple,” adds Curran. “Look up. The views from the top deck reveal architectural details you just can’t see from the sidewalk.”

Chicago by Sky: The City That Invented the Skyscraper

Skyscrapers weren’t just perfected in Chicago—they were born here. The devastating Great Chicago Fire of 1871 created an opportunity for innovation: steel-frame construction, pioneering architects, bold engineering, and a culture of upward ambition. Today, the skyline reads like a timeline of architectural history, and there’s no better way for groups to experience it than from above.

Chicago Architecture Center

Through immersive exhibitions, detailed scale models, and docent-led interpretation, the Chicago Architecture Center provides essential context for understanding how Chicago’s engineering innovation and visionary architects reshaped urban design. Celebrating its 60th anniversary in 2026, the Center remains a cornerstone for groups seeking deeper meaning behind the skyline.

“The CAC is the ideal starting point for an architecture tour,” says Eleanor Gorski, CEO and president of the Chicago Architecture Center. “We offer unparalleled expertise, customizable group experiences, and access to more than 75 docent-led tours.” These include walking tours, neighborhood explorations, bus tours, and the world-famous Chicago Architecture Center River Cruise aboard First Lady.

New in 2026, the Intro to Chicago Architecture walking tour takes groups through the city’s skyscraper canyons and stunning interiors, while popular returning tours such as Historic Treasures of Chicago’s Golden Age and Chicago Architecture: A Walk Through Time appeal to groups seeking immersive, off-the-beaten-path experiences at favorable group rates. Also this year, rotating exhibits—including the upcoming exhibition focused on bird- and animal-friendly design that emphasizes environmental responsibility in architecture—join the Chicago Gallery, Wrigley Field, and other permanent exhibits.

Skydeck Chicago

Perched atop the iconic Willis Tower, Skydeck Chicago delivers one of the city’s most unforgettable shared group experiences, providing a one-stop shop for visitors to get a taste of Chicago from new heights. At the heart of the experience is The Ledge, a bucket-list thrill that places guests inside glass boxes suspended 1,353 feet above the city, revealing sweeping panoramic views.

“No two reactions are the same,” says Randal Stancik, general manager at Skydeck Chicago. “That’s what makes The Ledge so special. It creates an unfiltered moment of awe that guests remember long after their visit.”

Beyond the views, Skydeck’s lower-level museum immerses groups in the city’s history, culture, and neighborhoods through exhibits such as a glowing Chicago River tunnel and a full-scale L train replica. Before taking the elevator to the 103rd-floor observation deck, groups can capture a standout photo moment beside the updated Willis Tower antenna replica.

“We’ve added dynamic colored lighting that mirrors the building’s real antenna lighting schedule, allowing guests to take photos with the same colors displayed atop the tower throughout the year, whether for holidays, sporting events, or special citywide moments,” says Stancik. “It’s quickly become a favorite stop in the museum.”

Groups benefit from flexible ticketing, early-morning visits to avoid crowds, and options for private events or early and late access. Skydeck’s 99th-floor event space accommodates up to 300 guests, and an on-site coordinator ensures a seamless event.

360 CHICAGO

Located along the Magnificent Mile, 360 CHICAGO offers a distinct perspective shaped by its proximity to Lake Michigan.

“Being steps from the lake gives our guests unique views from multiple vantage points, including sunsets to the west and sweeping skyline vistas,” says Jim Vozzella, senior sales manager at 360 CHICAGO.

From the bilingual (English/Spanish) entry experience to the 1,700 square feet of observation deck, the former John Hancock Center immerses guests on a journey through Chicago’s history in one stop that includes CloudWalk, CloudBar, and the thrill attraction TILT.

In 2027, 360 CHICAGO will introduce the city’s first multi-floor observation deck. Vozzella recommends groups book early to secure preferred visit dates and times during the expansion project.

Chicago by Sea: Riverwalks, Cruises, and Waterfront Wonder

Water defines Chicago just as much as steel. The river and Lake Michigan are gathering places, transportation routes, architectural classrooms, and social playgrounds—especially for groups. With accessible mobility for seniors and mixed-age travelers, built-in meal/cruise options, and excellent sunset and evening choices, this scenic entry into the city’s infrastructure and history provides full-day itineraries at a pleasant pace.

Riverwalk

Stretching along the south bank of the Chicago River, the Riverwalk places visitors in the center of the city’s most iconic buildings. Public art, cafés, boat docks, and shaded overlooks mean groups can regroup and absorb the city at sidewalk level.

“The Chicago Riverwalk is more than a scenic destination—it’s a cultural corridor that brings music, movement, and community together along the water,” says Department of Cultural Affairs and Special Events Acting Commissioner Kenya Merritt. “Through free, city-supported programming, including live music and seasonal activations, we continue to create welcoming experiences that allow visitors and residents alike to connect with Chicago’s creative energy in an iconic setting.”

Building a Multi-Day Group Itinerary

One-Day: Skyline to Shoreline

• Morning: Big Bus Tour orientation
• Late morning: Chicago Architecture Center visit
• Afternoon: 360 CHICAGO or Skydeck
• Evening: Navy Pier dinner + Ferris Wheel or lake cruise
  
  

Two-Day: Lakeside Icons & Culture

Day One: Field Museum → Shedd Aquarium → stroll Riverwalk

Day Two: Architecture river cruise → Old Town dinner → Second City show

Three-Day: The Complete Chicago

Day One: Sky: CAC + Skydeck + Magnificent Mile

Day Two: Sea: Riverwalk + river cruise + Navy Pier

Day Three: Story: South Side exploration + Wrigley Field tour

Dining, Shopping & Celebrating

Chicago’s food culture is legendary, but what makes it exceptional for groups is its range:

• Classic steakhouses for celebratory dinners
• Chicago-style pizza—always a crowd-pleaser
• River North and West Loop restaurants with private dining rooms
• Neighborhood bakeries, cafés, and dessert stops
• Lakefront brunch or cruise dining options

Shopping itineraries often include the Magnificent Mile, but artisan-focused experiences—neighborhood boutiques, museum gift stores, or Chicago Architecture Center’s design shop—offer memorable alternatives.

Navy Pier

For more than a century, Navy Pier has evolved alongside Chicago, and today it stands as a year-round entertainment district designed to serve diverse groups.

“We encourage planners to think in layers,” says Elizabeth Halajian, senior vice president of advancement at Navy Pier. “Pair marquee attractions like the Centennial Ferris Wheel with something unexpected like the Kiln Floating Sauna or the seasonal Winter Wonderfest.”

Just in time for the 100th anniversary of Route 66, Navy Pier will officially be designated as the symbolic starting point of the Mother Road, creating a unique “Pier-to-Pier” celebration in partnership with California’s Santa Monica Pier. Planned highlights include a Centennial Kickoff on March 25, a permanent Route 66 sign, and a themed fireworks display and “66 minutes of free Centennial Wheel rides” on June 6 (6/6/26). 

Groups can balance high-energy attractions such as the immersive theatrical Flyover ride with dining experiences ranging from iconic Chicago favorites Giordano’s and Harry Caray’s Tavern to private buyouts at Offshore Rooftop, the world’s largest rooftop venue.

“As a launch point for architecture cruises, sightseeing tours, dining cruises, and high-speed Seadog rides, Navy Pier connects visitors directly to Chicago’s waterways while offering planners exceptional flexibility,” says Halajian.

Chicago Through Stories: Museums, Legends, and Neighborhoods

Field Museum

The Field Museum anchors Chicago’s Museum Campus with immersive storytelling that spans cultures, civilizations, and the natural world. 

“With thousands of scientific and cultural items on display, it can be difficult to figure out where to start,” says Bridgette Russell, senior director of marketing and communications. “Our docent-led tours take visitors through time and space, offering a more immersive way to experience the natural world and human story.”

In Native Truths: Our Voices, Our Stories, visitors hear directly from Native American and Indigenous people through words, music, dance, and art. A visit to the Griffin Halls of Evolving Planet takesguests through billions of years of life on Earth, where they come face-to-face with fossils that chart evolution from single-celled organisms to modern humans. Highlights include the Elizabeth Morse Genius Hall of Dinosaurs, home to SUE, the most complete Tyrannosaurus rex ever discovered.

In May, the Field Museum will host the North American debut of Pokémon Fossil Museum, a limited-time exhibition that pairs beloved Pokémon with real-world fossils.

“One of the most rewarding experiences of working at the Field Museum is seeing visitors of all ages slip into a sense of child-like wonder,” says Russell. “Whether they are standing mesmerized beneath Máximo the Titanosaur or coming face-to-face with a jungle cat in the Hall of Mammals, the emotional connection creates a defining memory of their Chicago experience.”

Shedd Aquarium

The John G. Shedd Aquarium is preparing for its next century by reimagining historic galleries in ways that resonate with student and adult groups alike. In 2026, “Changing Oceans” joins the recently opened “Wonder of Water” and “Amazon Rising”—exhibits that blend interpretive signs, interactive tablets, pop-up science chats, and animal meet-and-greets designed to engage multiple generations at once.

“At Shedd, the gateway to conservation and learning comes through personal connections with nature,” says Johnny Ford, senior director of public relations. That philosophy guides how exhibits build from compassion to curiosity to inspiration.

Seasonal programming adds energy and flexibility to group itineraries. Favorites include the Stingray Touch habitat (open spring through fall) and after-hours events such as Jazzin’ at the Shedd, which pairs live music with skyline views and a relaxed evening atmosphere.

As guests move through the aquarium, the Beaux-Arts architecture—complete with aquatic-themed moldings and Greco-Roman columns—frames the experience. “In many ways, a visit to Shedd Aquarium is equally exciting for both nature and history lovers,” Ford says.

Renovations also prioritize accessibility, with improved pathways, sensory-friendly spaces, and dual-language interpretation. And few moments delight groups more than encounters with Shedd’s long-lived, famously curious penguin colony.

Wrigley Field

Tours of Wrigley Field are available throughout the year and take groups behind the scenes of one of America’s oldest ballparks.

“From stepping into the Cubs dugout and visiting the press box to walking on the field and standing beside the iconic ivy-covered outfield walls, the experience allows guests to walk where baseball legends have played,” says Cubs Vice President of Ticket Sales Steve Brauer. The hand-operated scoreboard and the famous red Marquee further connect visitors to the ballpark’s living history. 

Wrigley Field supports smooth group visits through pre-arrival communication that helps tour planners manage directions, bus drop-off and pickup, security procedures, and event timing. When planning a visit, groups of all sizes can choose from reserved seating blocks, private suites, or social spaces such as the YETI Yard.

Beyond baseball, Wrigley Field has hosted concerts, festivals, and additional sporting events such as basketball and even ski-jumping. In 2026, fans will have the chance to see stand-up comedy, live music, and more, reinforcing its role as a cultural landmark within the city.

The Second City

Groups looking for an authentic taste of Chicago’s culture and arts scene will find it at The Second City. “The Second City is a uniquely shared experience,” says Colleen Fahey, vice president of marketing and sales operations. “Smart, scripted comedy combined with live improv creates surprising, memorable moments that can’t be replicated.”

In 2026, The Second City will debut more than 10 new productions across its stages, including a new Mainstage revue, the Black Excellence production Black and Highly Flavored, and a fully improvised e.t.c. Theater show. New behind-the-scenes tours and brand-focused group experiences will roll out by summer, adding new customization options.

“We love groups!” says Fahey. “We seat parties together, host private events, and offer waived fees and dedicated coordinators.”

As one of Illinois’ top tourist attractions, The Second City has shaped the city’s comedic identity for more than six decades, delivering an authentic, laugh-filled dose of Chicago’s creative history.

Obama Presidential Center

The South Side holds some of Chicago’s most meaningful cultural sites: Bronzeville, historic churches, jazz landmarks, family-owned businesses, public art, and community-led initiatives. Visitors often cite this as the most eye-opening and emotional part of their trip.

At the heart of the South Side’s next chapter is the Obama Presidential Center, opening in summer 2026. Located in Jackson Park, the museum aims to become a civic, educational, and community campus with broad national and international significance.

“This deeply personal project for President Obama features a museum, public library, gardens, community spaces, and event venues, all located in the culturally rich Hyde Park area,” says Choose Chicago’s Nucci.

Take a behind-the-scenes tour of the Center with President Obama himself at obama.org/stories/construction-update-december-2025. To confirm the most current visitor information, visit obama.org.

A City That Never Stops Looking Up

For groups planning 2026 and beyond, Chicago’s soaring viewpoints, glittering river reflections, and layered stories signal you’ve arrived somewhere truly special. Says Nucci: “The character of a destination is what stays with people, and Chicago’s character is what keeps people coming back.”

A successful group itinerary to Chicago begins by connecting with the team at Choose Chicago.  Call (312) 567-8500 or visit choosechicago.com.

Pamela Brossman is the senior editor of ABA’s Destinations magazine.

Photo credits: ©City of Chicago; Kyle Flubacker; Pamela Brossman; Skydeck Chicago; 360 Chicago; © Field Museum; Martin Baumgaertner; Timothy M. Schmidt; ©Shedd Aquarium/Brenna Hernandez; The Chicago Cubs; The Obama Foundation.