Chicago Things To Do

Something Special for Everyone

Chicago becomes an even more extraordinary destination when meeting attendees, spouses, groups, and others get to enjoy some of the city’s out-of-the-ordinary experiences. Tailor your visit to include some of these unique, insider activities.

Be sure to download the documents listed below to enjoy prearranged activities.

… a vibrant city with a treasure trove of outstanding museums …

Chicago Botanic Garden

Chicago Botanic Garden is an enchanting place with nine islands, sparkling lakes, and discoveries around every corner. Your group will enjoy a variety of tours season to season as well as outdoor experiences – and you can also add demonstrations and workshops, special events, shopping, music, and scenic dining. Better get booking! Chicago Botanic Garden is located just north of downtown Chicago in Glencoe.

The Historic Chicago Theatre: Venue Tour

Come see behind the scenes of the city’s most iconic theatre! Our Venue Tour encompasses historical and architectural highlights of the building, including the grand lobby areas, majestic auditorium and backstage space where performers through the years – including Sammy Davis, Jr., Liza Minnelli, Conan O’Brien, Frank Sinatra, and many more – have left their autographs on dressing room walls. Our guides will share stories of the visionaries who opened The Chicago Theatre, whose influence on popular entertainment in Chicago is still recognized today. Tours also include the photo exhibit in the lower lobby, “Chicago: Three Centuries of Theatres.”

Chicago ShopWalk – Guided Neighborhood Tours to Chicago’s Best Boutiques

Explore Chicago’s hippest neighborhoods for shopping with ShopWalk. Choose from one of five lovely neighborhoods, each with its own character. You’ll visit unique shops featuring emerging designers and latest trends plus hard-to-find urban boutiques you won’t find back home or on the Magnificent Mile. Your group will meet up at a local café, then take off on foot to find exciting fashion, shoes, and accessories. and gifts. ShopWalk VIP treatment includes exclusive shopping discounts, personal styling, neighborhood trivia, and time for stops at chocolate shops, coffee houses, and one-of-a-kind cafes.

Urban Shop Guide Boutique Shopping Tours

Visit Chicago’s newest boutiques and shopping landmarks on a tour with Urban Shop Guide. Some of the city’s bestkept shopping secrets are only a few minutes from downtown in Chicago’s vibrant neighborhoods. We will meet you at a predetermined location only a short taxi, bus or train ride from Michigan Avenue, then lead you on a guided tour of the best neighborhood boutiques. Luxury vehicle tours are also available. Urban Shop Guide will provide a trip itinerary that highlights boutiques, designers, hot restaurants, and history of the neighborhood. Enjoy special discounts, treats, and offers in many stores.

Chicago Chocolate Tours

Take a Chicago Chocolate Tour and enjoy the sweetest tour in town! Your tour guide will escort you on a walking and tasting tour of unique Chicago chocolate shops, where you will learn about the history and health benefits of chocolate, meet some chocolate makers, and sample the chocolate specialties at each location. Find out why dark chocolate is healthier, whether white chocolate is really chocolate, and whether chocolate is really an aphrodisiac. Tour routes include the Magnificent Mile, Downtown Loop, and there is time to shop at each store if you choose. Uplift through chocolate!

Chicago Dine-Around

Embark on a culinary adventure to Chicago’s finest restaurants. Guests are chauffeured around the city to enjoy hors d’oeuvres served at the first restaurant, the main course at a second restaurant, and dessert at a third restaurant. This Progressive Dining Tour offers a unique, fun, and exciting way to experience Chicago dining at its finest restaurants, interact with others, and see the city. Guests indulge on the scrumptious food selections, eclectic ingredients and generous portions presented uniquely by the restaurants. This Progressive Dining Tour brings the culinary spirit to life!

Chicago Food Planet Food Tours

Hungry for an authentic Chicago culinary and cultural experience? Chicago Food Planet specializes in Food Tours through Chicago’s most historic, delicious neighborhoods. All tours include mouth-watering food tastings from “mom and pop” specialty food stores and one-of-a-kind ethnic eateries while offering a narrated glimpse into Chicago’s rich history and treasured architecture plus dazzling restaurant recommendations. Suitable for all age groups and fitness levels, our experiences are enjoyed by native Chicagoans and visitors alike.

Cooking Fools

Cooking Fools creates custom cooking events for any size group up to 75. Our programs are a different, fun, and exciting alternative to dining out. Your event can be based on an international menu, a type of food, or a theme of your choice. Our Chef instructors will lead your group through hands-on cooking activities to produce a delicious meal that everyone will enjoy. We are located in a spacious urban loft in the heart of Bucktown / Wicker Park, just north of downtown Chicago at 1916 W. North Ave. Call us for more details about creating a memorable event for your guests.

The Hearty Boys Caterers Present HBTV

HBTV is the freshest idea to come along in years! Original Food Network Stars and “Talk With Your Mouth Full” authors Dan Smith and Steve McDonagh take your group on a one-of-a-kind behind-the-scenes culinary journey! This unique Chicago hands-on experience begins with an on-camera cooking demo by Dan and Steve. In their fun and approachable signature style, they’ll relate the tricks of the TV trade. Within the hour your group will be organizing production teams and testing out their culinary chops in front of the live camera! It’s a spectacular time of great food, fun, and “cooking karaoke!”

American Girl Place® Chicago

It’s a place where the magic of the past and present come to life in dazzling ways. Parents, daughters, and even grandparents can celebrate all of the fun and excitement of girlhood. With so many different experiences, it’s easy to plan a fun-filled day. Start with a meal in the American Girl Cafe (private meal options are available), then get ready to explore our store. We have special group packages for our Photo Studio and Doll Hair Salon. Inquire how we can customize your visit to fit your group’s needs. It’s more than a store; it’s an experience!


Bloomingdale’s spousal and group activities are designed to give your clients a unique shopping experience in America’s most famous fashion store. World-renowned as a leader in style and fashion, Bloomingdale’s offers special services and events to meet your client’s interest and budget. Group size can vary between 5 – 100 attendees, depending on event. Some of our most popular events include Breakfast at Bloomingdale’s prior to store opening, a private beauty day with cosmetics, and an afternoon wardrobing presentation with our personal shopper.

Macy’s on State Street

An exciting array of activities showcases the world’s second largest department store – beginning with a Flagship Tour of its history and breathtaking architecture. Explore décor and furniture design trends in the Trend House, then meet with a member of the design staff to Identify Your Decorating Personality. Discover wardrobe solutions and fashions for various occasions in Fashion Trends plus makeup and skincare innovations during Beauty Breaks. Foodies will love Frango Fun and the Frango Cooking Class, Culinary Council Cooking Class, Wine Tastings, and Salsa & Margaritas. State Street Favorites Lunch shows how to make top-sellers from the store’s restaurants.

The 900 Shops

The 900 Shops at 900 North Michigan Avenue feature Bloomingdale’s and over 70 luxury retailers on seven levels. Out-oftown guests can visit the Concierge Desk to receive the Exclusively 900 Card, which includes incentives and premier savings throughout the center. Additionally, customers who spend more than $100 at The 900 Shops can redeem a signature gift. For groups of 10 or more, The 900 Shops will personalize the Exclusively 900 Cards and mail them to the desired location prior to the group’s visit. Looking for an enhanced shopping experience? Groups can indulge in a customized VIP shopping program at The 900 Shops.

The Oprah Store

Located on the south corner of Washington and Carpenter streets, The Oprah Store is Harpo, Inc.’s first free-standing retail store. This specialty store offers more than 900 unique products, including authentic South African arts and crafts, a signature line of baby products, workout wear, souvenirs, gifts, and other merchandise that represents the style and taste Oprah celebrates and shares on “The Oprah Winfrey Show” and in the pages of O, The Oprah Magazine. A special feature is “Oprah’s Closet” – a wardrobe of items once worn or treasured by Oprah, now available to the public. All sales from “Oprah’s Closet” benefit Oprah’s Angel Network.

The Shops at North Bridge

Situated along Chicago’s famed Magnificent Mile, The Shops at North Bridge features an enticing mix of 50 world-class specialty shops, 20 sumptuous restaurants, five elegant hotels and one magnificent shopping center, anchored by Nordstrom. The Shops at North Bridge Concierge can customize an experience based on the spouse group’s interest to include trunk shows, informal modeling, wardrobe consultations, fashion shows, and private shopping hours. Fees do apply in some cases.

The Theatre Experience at Broadway In Chicago

This year Broadway In Chicago is proud to present at Chicago’s finest theatres: Pre-Broadway world premiere musical; THE ADDAMS FAMILY; THE JERSEY BOYS – now in its second smash year; and the hottest hit productions from Broadway for 2009, including MARY POPPINS, CATS, SPRING AWAKENING, THE TEN TENORS and more. Call Broadway In Chicago Group Sales to book a group of twenty or more using the code CCTB and ask about weekday discounts, post show Q&A with a cast member, souvenir show merchandise for each attendee, and adding a pre show cocktail reception in the Suite.

The Second City

Treat your group to a night out at The Second City, presenting the best in Chicago comedy every night of the week. A true Chicago landmark, The Second City has been entertaining corporate and not-for-profit groups for almost 50 years. The Second City can also create a completely original, customized program for your group. Second City Communications will design a unique, customized performance or workshop which can be presented at The Second City or travel to your group.


ComedySportz is a fun, fast-paced comedy show that’s great for the whole family, for business entertainment, and for groups of all types. Playing improvisational comedy as a sport, two teams battle for laughs and points as they make up scenes, games and songs on the spot, and the audience votes for the winners. We’ll tailor the show to your group, using customized information you provide to create a personal and fun performance with lively audience interaction.