With its soaring skyscrapers and beautiful lakefront setting, Chicago is an inimitable city in the Midwest that also has a place in people’s hearts for icons such as the Chicago Cubs, legendary blues music and famous comedians.

Tapping into these iconic experiences through off-site events is one of the best ways for planners to infuse agendas with a distinctly Chicago flair.
Following are some of the top only-in-Chicago picks for planners.


Wrigleyville, the district surrounding Wrigley Field, is one of the city’s most popular attractions and even moreso since the Chicago Cubs became World Series Champions in 2016. Wrigleyville is an increasingly vibrant area of the city, with several new as well as tried-and-true venues for groups.

Its centerpiece is Wrigley Field, which was built in 1914 and is the second-oldest park in Major League Baseball after Fenway Park in Boston. Wrigley Field, nicknamed “The Friendly Confines,” has preserved its original beauty, charm and traditions, including its hand-operated scoreboard and ivy-covered outfield walls.

Booking tickets to a game at Wrigley is a great way for groups to experience an authentic slice of Chicago for an afternoon, while it can also host group events.

Wrigley Field
Wrigley Field, Chicago

Spaces for groups include Budweiser Patio and Left Field Porch, which are both situated in the famous Budweiser Bleachers, as well as several climate-controlled suites. On non-game days, groups can play catch or softball or even have a homerun derby on the historic field, with access to indoor batting cages and bullpen sessions.

A major new expansion at Wrigley Field includes Gallagher Way, an open-grass area that accommodates receptions for up to 2,000 people and adjacent to the park, the American Airlines Conference Center, which accommodates meetings and social occasions for up to 300 people.

The center features functional conference rooms that include audiovisual equipment and can be divided into smaller spaces, while a folding NanaWall system opens out to a patio overlooking Wrigley Field and the outdoor plaza.

The center features extraordinary views of the ballpark and Chicago skyline.

Each meeting includes a personal touch of Wrigley Field, as attendees receive Cubs-themed paper and pens, for example.

With Gallagher Way’s many distinct venues surrounding Wrigley Field, planners can choose from an a variety of ambiances, including restaurants, outdoor settings, modern and industrial options, corporate environments and party backdrops. Additionally, a variety of group sizes can be accommodated.

The project also features the hip Hotel Zachary at Gallagher Way, which has a variety of dedicated meeting space and other unique venues for groups.

Another option for group gatherings during a Cubs game is Wrigley Rooftops, a set of 11 rooftops overlooking Wrigley Field, all with indoor and outdoor levels.;

A meeting can be held inside in different settings, including boardroom, presentation or classroom setups, before the group moves outside for a game.

Wrigley Rooftops is one of the most unique experiences of a baseball game, as attendees sit on top of buildings across the street from Wrigley Field and have views of the field and the city.


Planners can take events sky high at two of Chicago’s most famous landmarks: Willis Tower and the John Hancock Building, both set in the heart of downtown and offering unforgettable views of the city, Lake Michigan and up to four states in the distance.

The 110-story Willis Tower, standing 1,450 feet tall, is the highest building in the Western Hemisphere. It’s 99th floor is available for private events, offering the option for private VIP access to The Ledge at Skydeck, the famous glass-floor balcony extending four feet outside Willis Tower—1,353 feet over Chicago.

The venue can host fully catered dinners for up to 175 people or receptions of up to 300 people.

No trip to Chicago is complete without a drink in the Signature Room Lounge on the 96th floor of the John Hancock Building, particularly at night, when the city and suburbs unfold like a neon patchwork quilt. Just one floor below, The Signature Room on the 95th also offers breathtaking views and group spaces. The venue features 10 private event settings and buyouts for up to 1,000 guests.

Architecture Cruises

Chicago is legendary for its architecture, and Chicago’s First Lady, the only cruise partnered with the Chicago Architecture Center (CAC), is an a truly memorable way to take it all in. Volunteer docents provide a detailed narrative and fascinating facts of Chicago’s various architectural styles and the stories of the people who designed and built the city.

architecture cruise
Architecture Cruise, Chicago

Groups can charter a private vessel for up to 250 people for the 90-minute Chicago river architectural tour, featuring indoor and outdoor seating and a full-service bar. The open-air top deck offers panoramic, 360-degree views of the city. Excursions can also be fully catered.

The Second City

Anyone who is a fan of Saturday Night Live back in the 1970s would be highly impressed to read the list of comedians who got their start at The Second City, Chicago’s historic improvisational comedy institution.

The Second City Theatre opened in 1959 and has since become one of the most influential and prolific comedy theatres in the world. Since its debut, The Second City has consistently been a notable starting point for comedians, award-winning actors, directors and others in show business, including Bill Murray, Gilda Radner, John Candy, Dan Aykroyd, Del Close, Eugene Levy, Catherine O’Hara, Nia Vardalos, Ryan Stiles, Mike Myers, Steve Carell, Tina Fey, Amy Poehler, Stephen Colbert.

With three theaters, The Second City is available for group events of up to 500 people, giving participants a chance to enjoy the latest in cutting-edge sketch comedy combined with songs and improv.
Full-service catering is available or pre-show dinner packages for up to 100 people at The Second City’s 1959 Kitchen & Bar.

Buddy Guy’s Legends

Chicago is a mecca for numerous musical genres, blues and jazz being standouts in particular. Keeping the city’s rich blues tradition alive is Buddy Guy’s Legends, owned by the renowned guitarist himself, who plays a sold-out series of shows at the club each January.

Grammy trophies, worn guitars and Guy’s signature polka-dot guitar straps are fixtures on the club’s walls, which stages local, national and international acts nightly.

Buddy Guy’s Legends is available for private events of from 30 to 600 people, with live music and fully catered soul food options.

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