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Year round guide to Chicago

Looking for ways to encourage mingling after the day’s meetings are over? Chicago offers lots of options for corporate get-togethers. From outdoor concerts in the summer to cozy comedy shows in the winter, these classic Chicago after-hours outings make free time a fun time for your attendees, especially first-time visitors to the Windy City.


Grant Park Music Festival

Millennium Park is Chicago’s beautiful playground for the arts, situated right in the heart of the Loop, and is a great place for a corporate outing. Plan a dinner at ParkGrill, located at the scenic gateway to Millennium Park. Reserve the private Founder’s Room (seating 32), or arrange for semi-private dining accommodating 25+ guests. Seating is also available on Park Grill’s outdoor patio, which is one of the largest in the city. Park Grill can provide a special menu of its contemporary American cuisine for your group.

After dinner, make time to snap a group shot in front of the reflective Cloud Gate sculpture (affectionately called “The Bean”) and view the dazzling Crown Fountain, before making your way over to the Jay Pritzker Pavilion to catch a Grant Park Music Festival concert. The free Grant Park Music Festival has been a summer tradition in Chicago for more than 80 years, featuring classical music performed by world-class orchestras. Groups of 10 or more can arrange for reserved seating in the Seating Bowl; while groups of 50 – 100 can book the Choral Balcony (for select concerts), with an option of hosting a backstage reception before or after the show. The Grant Park Music Festival runs from mid-June through mid-August.



Architecture buffs will love the Chicago Architecture Center river cruise aboard Chicago’s First Lady Cruises. Voted one of the top 10 tours in the U.S. by TripAdvisor, this popular 90-minute cruise is narrated by CAF-certified docents who point out more than 50 architectural gems along the Chicago River. As you pass by you’ll hear about Chicago’s fascinating history and the design giants who shaped the city’s world-famous skyline. Book a group tour for 10 or more; discounts are offered for 20+.

Afterwards, stop for drinks at City Winery Chicago Riverwalk. Located right on the Chicago River along the scenic Chicago Riverwalk, at City Winery you can arrange for a semi-private reception for up to 200 guests in the breezy wine garden.

Or continue the architecture theme with a trek up to 360 CHICAGO, located on the 94th floor of 875 N Michigan (formerly the John Hancock Center). Named one of the Best Views in America by Travel + Leisure, the observation deck offers 360-degree views of the city, Lake Michigan and four states. And don’t miss 360 CHICAGO’s thrilling TILT, a huge steel-and-glass bay window that actually tilts forward, giving visitors a downward-facing view of the city from 1,000 feet up in the air. Afterwards, grab a cocktail at Bar 94, 360 CHICAGO’s bar and cafe. Group rates for 20 or more are available for 360 CHICAGO admission and Tilt tickets.


The Second City
Second City

Nothing warms up a wintry Chicago night like a good belly laugh, and there’s no better place to get your grin on than The Second City. This legendary comedy theatre, known for its hilarious improv-based sketches, has produced stars that include Tina Fey, Bill Murray, and Steve Carrell. Start the evening with a pre-show dinner at the on-site 1959 Kitchen & Bar. This sleek restaurant has a laid-back neighborhood bar feel, with exposed brick and photos of Second City comedians hung on the walls. Group pre-theater dinner packages include selections from its menu of organic pub fare.

Then it’s on to the show. The Second City has been making audiences laugh for more than 50 years with hilarious sketches that include funny takes on current events, as well as a bit of song and dance. Shows take place seven nights a week, with various revues that feature up-and-coming performers who just might be the next big comedy stars of tomorrow. Make reservations for groups of 16 or more.

For the ultimate convenience, combine dinner and a show with one easy booking by Chicago Dine-Around. This guided experience includes pick-up and drop-off at your hotel or preferred downtown location in a stylish coach bus, dinner at one of Chicago’s best restaurants and show tickets to a performance at one of the city’s renowned theatres. All components and logistics are handled and included into one invoice for hassle-free planning.



Spring means one thing in Chicago: baseball. And there’s no better place to experience America’s favorite pastime than during a Chicago Cubs game at historic Wrigley Field. Before the game, join Wrigley Field Tours for a behind-the scenes look at the historic century-old ballpark, which include great photo opps on the field. Book a private tour for groups of 1 – 10 or 10 – 50 that comes with your own personal tour guide.

Then get ready to watch the 2016 World Series Champion Chicago Cubs crack the bat in the friendly confines of Wrigley Field. For a VIP experience, reserve the Fannie May Bleacher Sweet. Located in center field with access to the legendary Budweiser Bleachers (a favorite seating spot for die-hard Cubs fans), the luxury temperature-controlled suite can accommodate 70 – 100 guests, and includes a food-and-beverage package of ballpark eats.

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