2021-05-15 07:00:09
These themed full-day itineraries will help your group make the most of their time in Chicago with ideas for the best places to experience the city’s architecture, outdoors, and culture. DAY 1: ARCHITECTURE MORNING Start your day with spectacular city views from Skydeck Chicago, located on the 103rd floor of the Willis Tower (the second-tallest building in the country), and treat your group to breakfast on The Ledge, a thrilling glass-floored balcony. At the Chicago Cultural Center, take a free private group tour (advance booking required) and marvel at the world’s largest stained-glass Tiffany dome. Don’t miss the free classical Dame Myra Hess Memorial Concerts, held every Wednesday afternoon. Across the street at Millennium Park, take a selfie in the reflection of Anish Kapoor’s mirrored Cloud Gate sculpture (nicknamed “The Bean”). Splash around in the multimedia Crown Fountain, then check out the breathtaking Frank Gehry-designed Jay Pritzker Pavilion. Go behind the scenes of iconic performing arts venues by bringing your group on the Marquee Tour at The Chicago Theatre or the Backstage Tour of the Lyric Opera of Chicago, which explores the Art Deco-style theatre. On the enhanced Rookery Light Court + Burnham Library Tour led by the Frank Lloyd Wright Trust, explore Daniel Burnham and John Root’s 1888 Rookery Building, with its light-filled Frank Lloyd Wright-designed lobby. You’ll also see the Burnham Library, where architects met to discuss plans for the 1893 Chicago World’s Fair. AFTERNOON Choose one of the many architecture-themed walking tours offered by the Chicago Architecture Center, such as Art Deco Skyscrapers or Tiffany Treasures. From March through November, glide past Chicago’s stunning cityscape on an architecture boat cruise with the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady (90 minutes), Mercury Chicago’s Skyline Cruiseline (90 minutes), Shoreline Sightseeing (60 minutes), or Wendella Tours & Cruises (45–90 minutes). Spend some time shopping on The Magnificent Mile while passing landmark structures such as the Wrigley Building, Tribune Tower, and DuSable Bridge. Continue on to historic State Street to visit Macy’s State Street, housed in the turn-of-the-century Marshall Field and Company Building. Or, head out of the city for the afternoon with a trip to west suburban Oak Park’s Frank Lloyd Wright Historic District. This architectural treasure trove is home to the storied Frank Lloyd Wright Home and Studio where the architect lived and created his famed Prairie style of design, as well as the striking Unity Temple. EVENING At night, enjoy a unique view of the summer Navy Pier fireworks from TILT at 360 CHICAGO, an exhilarating experience that tilts you over the edge of the observation deck, 1,030 feet above The Magnificent Mile. Or, bring your group to experience the magic of the theatre. Watch original plays and literary adaptations at Lookingglass Theatre Company on The Magnificent Mile. In the Loop, catch a concert at the Auditorium Theatre, or a dance performance by the Joffrey Ballet at the Lyric Opera House. Or venture outside of downtown and into the neighborhoods to experience fast-paced improv comedy at The Second City in Old Town, or see headliner stand-up comedians at the Laugh Factory in Lakeview. DAY 2: OUTDOORS MORNING Kick-start your day with some fun and fresh air. Maggie Daley Park features a 40-foot Climbing Wall, winding Skating Ribbon (rent roller-blades and scooters during the summer and ice skates in the winter), the 18-hole City Mini Golf course, and the Play Garden for visitors ages 12 and under. Then, explore the city on two wheels during Chicago’s Ultimate City Bike Tour with Bobby’s Bike Hike. On this three-hour excursion, your group will pedal through sprawling urban parks, past notable museums and attractions, and along the Lakefront Trail, an 18-mile (29 km) paved path that hugs Lake Michigan. Another two-wheel option is the Chicago Lakefront Museum Campus Tour by Absolutely Chicago Segway Tours, offering views of the lakefront and Chicago’s Museum Campus — home to the Field Museum, Shedd Aquarium, and Adler Planetarium. Cool off afterwards at a downtown beach. Oak Street Beach, which is great for people watching, is located close to The Magnificent Mile. Or head a little further north and go swimming at popular North Avenue Beach. All of Chicago’s beaches are admission-free. AFTERNOON At Navy Pier, the city’s top lakefront destination, take your pick from numerous attractions and activities. Get a thrill on carnival rides at Pier Park and marvel at panoramic views of the city as you soar nearly 200 feet in the air on the Centennial Wheel. Catch a free live show at the Lake Stage or City Stage at Polk Bros Park. Then, zoom along the waters of Lake Michigan in a jet-propelled speedboat with Sea Dog Cruises, departing from Navy Pier. Get up-close to nearly 200 species of animals, from polar bears to gorillas, at the free Lincoln Park Zoo, which is one of the oldest zoos in the country. Enjoy pre-dinner drinks aboard Odyssey Chicago River with a two-hour Cocktail Cruise featuring passed hors d’oeuvres, light bites, and dramatic city views from the all-glass vessel. EVENING Stroll the Chicago Riverwalk, a pedestrian walkway on the Chicago River with plenty of attractions, public artwork, and waterfront cafes, bars, and restaurants. From here, take the Sunset Tour with Urban Kayaks and paddle along the Chicago River to learn about the city’s history. Once the sun goes down, make your way to the jetty section of the Chicago Riverwalk, where you can watch Art on theMART, a free display of colorful light projections shown nightly from April through December. From June through August, watch free outdoor concerts and movies during the Millennium Park Summer Music & Film Series. The shows at Jay Pritzker Pavilion typically begin at 6:30 p.m., so arrive early for a seat or spot on the lawn. Millennium Park is also home of the Grant Park Music Festival, the country’s only free outdoor classical music series, held from June through August. Every Wednesday and Saturday night from Memorial Day through Labor Day, don’t miss the Summer Fireworks show at Navy Pier, where the night sky is filled with dazzling bursts of fireworks synchronized to music. DAY 3: CULTURE MORNING Spark your creativity at the Art Institute of Chicago, where your group can peruse one of the world’s largest collections of Impressionist paintings — from Claude Monet to Georgia O’Keeffe to Vincent van Gogh — as well as ancient sculptures, miniature dioramas, stained glass Chagall windows, and medieval armor. Be sure to take a picture with the Historic Route 66 sign near the main entrance on Adams Street. Or, get a glimpse into the minds of modern artists through the ever-changing exhibits at the Museum of Contemporary Art. Experience musical history on the Chess Records Tour at Willie Dixon’s Blues Heaven Foundation, highlighting American blues and rock ‘n’ roll greats like Etta James and Muddy Waters who recorded at this legendary studio. AFTERNOON Chicago is a diverse city representing more than 100 countries within its 77 distinct neighborhoods, so spend a few hours exploring some of these vibrant communities. Immerse yourself in the colorful Latinx culture of the Pilsen neighborhood, where you’ll find eye-catching murals, family-owned Mexican restaurants, panaderías, and the free National Museum of Mexican Art, showcasing more than 9,000 pieces spanning from ancient times to modern day. In culturally diverse Hyde Park, learn about the achievements of Africans and Americans of African descent at the DuSable Museum of African American History. Take a guided tour of the Frank Lloyd Wright-designed Robie House, a UNESCO World Heritage Site. Then stroll through the free Garden of the Phoenix in Jackson Park to take in the beauty of Japanese culture. On The University of Chicago campus, visit two free museums: the Oriental Institute Museum (housing amazing ancient artifacts) and the provocative Smart Museum of Art. EVENING For nighttime entertainment, bring your group to one of Chicago’s renowned theatres. With Broadway in Chicago, watch hit Broadway musicals and beloved classics on a variety of downtown stages. For daring and thought-provoking productions that touch on social, political, and personal themes, take a seat at the Steppenwolf Theatre Company. Meanwhile, Buddy Guy’s Legends pairs nightly blues performances with New Orleans-inspired fare, making it easy to plan dinner and a show in one convenient location. Other classic Chicago blues clubs to check out include Kingston Mines and B.L.U.E.S., both located in Lincoln Park. Or, head to the Ravenswood neighborhood and sample locally made brews on Malt Row, home to some of the city’s best microbreweries, as well as Chicago’s first craft distillery, KOVAL. Find information on fun neighborhood festivals at choosechicago.com/events. For great dining ideas, go to choosechicago.com/tools. Discover even more group itineraries at choosechicago.com/tools.
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