In the spring or summer, meet in Millennium Park. It's right downtown, prime for an eye-popping stroll and casual get-together. After taking a group picture in front of Anish Kapoor's Cloud Gate, the silvery "Bean,” attendees can catch a concert at Pritzker Pavilion or gather at the hidden Lurie Garden.
Host an intimate and entertaining outing and book a 90-minute architecture tour. Viewing the skyline by boat is the quintessential way to go. Grab a seat on deck and look up as cloud-poking towers glide by. Vessels depart from the river docks beneath Michigan Avenue and from Navy Pier. Plan gatherings around a festival (in summer) or brewery (in winter).
In June, half a million fans flock to the Chicago Blues Festival to hear guitar notes and bass lines. In July, grilled meats spice the air for Taste of Chicago. In September, the Berghoff Oktoberfest brings Bavarian-style revelry to the city with German beer and music. Lincoln Park's ZooLights draws winter crowds for a free display of more than a million lights. Any time of year is perfect for visiting Lagunitas Brewing Company, the city's biggest beer maker. Guides give free tours daily that roam by shiny tanks bubbling with Lagunitas' hoppy suds. Many events offer VIP experiences that groups can book in advance.
After dinner, enjoy a show at one of Chicago's many acclaimed theatres. Home grown Goodman Theatre, Lookingglass Theatre Company and Steppenwolf Theatre Company are known for powerhouse productions.
If laughter is what you seek, visit The Second City, the birthplace of improvisation comedy.
Chicago's glamorous rooftops also provide ample opportunity for unforgettable evenings. Soak up the skyline and creative cocktails at ROOF on theWit or gaze across the lakefront at J. Parker.
Of course, no Chicago experience is complete without incorporating the iconic music scene. Catch the nation's best blues players at Buddy Guy's Legends or classic Chicago sounds at Andy's Jazz Club or City Winery.
For the sports fans, Chicago teams span all seasons. Book a suite and bring attendees together for a game. The Cubs play at ivy-clad Wrigley Field, a 100-year-old shrine for baseball fans, while the White Sox swing at mod U.S. Cellular Field. The Bears (football), Blackhawks (hockey) and Bulls (basketball) are hot tickets when the weather cools. The Fire play soccer in suburban Ridgeview.
Ten museums, including The Field Museum and Shedd Aquarium, have taken the lead in environmentally friendly practices, from green business operations to green exhibits.