Chicago’s skyline has been shaped by some of the biggest names in architecture — Louis Sullivan, Frank Lloyd Wright, Mies van der Rohe, and Daniel Burnham, included. Explore the city’s groundbreaking buildings with this one-day itinerary, and find yourself whisked from walking tours and boat excursions to sky-high city views and theatrical masterpieces.

Morning: Expert-led Chicago architecture tours

Start your day with a tour led by the experts at the Chicago Architecture Center. With more than 85 tours, it may be hard to choose just one. But a sure bet is the Historic Skyscrapers downtown walking tour that explores some of the world’s earliest skyscrapers. Rising from the ashes of the Great Chicago Fire of 1871 that destroyed much of the city, these tall buildings transformed Chicago into a center of skyscraper design and engineering.

Highlights of the 2-hour tour include the ornate Rookery Building designed by Daniel Burnham, with an interior atrium reimagined by Frank Lloyd Wright; Dankmar Adler and Louis Sullivan’s Auditorium Building; and the Art Deco-styled Chicago Board of Trade building, designed by Holabird and Root.

Insider tip: Your ticket includes admission to the Chicago Architecture Center, where you can learn even more about skyscrapers with stunning scale models at the Building Tall exhibit.

Afternoon: Historic buildings and river cruises

Have lunch at The Walnut Room, opened at the former Marshall Field’s in 1907, America’s first department store restaurant. Today, it’s located in the flagship Macy’s on State Street, where it still retains its dark walnut paneling and elegant Austrian chandeliers. The Macy’s building itself is a National Historic Landmark and listed on the National Register of Historic Places.

After lunch, head to the Chicago Riverwalk and hop on the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady Cruises. Voted one of the top tours in the U.S. by TripAdvisor users, this popular 90-minute cruise is narrated by Chicago Architecture Center-certified docents who point out more than 50 architectural gems along the Chicago River. You can also set sail with Wendella Tours & Cruises or Shoreline Sightseeing Company for amazing views of the river and city skyscrapers.

Friday Night Flights

Evening: Sky-high views and theatrical vistas


Next, head to the top of two of Chicago’s tallest buildings for a sky-high view of the city. (Note: You can skip the lines and get discounted admission with a CityPASS or Go Chicago Card.)

As soon as you reach Skydeck Chicago on the 103rd floor of Willis Tower (formerly the Sears Tower), you’ll be wowed by jaw-dropping panoramic views that span up to four states and nearly 50 miles on a clear day. Step out on The Ledge, an enclosed glass balcony that extends approximately four feet beyond the building’s facade, 1,353 feet up. Time your visit at sunset to see the city transform from day to glittering night.

Get another adrenaline rush at 360 CHICAGO on the 94th floor of 875 N. Michigan Ave. (formerly the John Hancock Center). The highlight of your visit is undoubtedly TILT, a huge steel-and-glass bay window that’s hydraulically powered to tilt forward, giving you a heart-pounding, downward-facing view of the city from 1,030 feet in the air.

For dinner, go up one floor to The Signature Room at the 95th and enjoy even more incredible views as you dine on fine cuisine and sip on decadent cocktails.

Jump in a cab or take a picturesque walk to end the evening at the Auditorium Theatre of Roosevelt University or iconic Chicago Theatre.

At the Auditorium Theatre, catch a classical concert or ballet performance, among other shows, and marvel at the beautiful architecture. Dankmar Adler’s acoustic design for the theatre is considered a masterpiece of sound, while Louis Sullivan’s signature ornamentation (including 24-karat, gold-leaf ceiling arches) adds grace and elegance to this grand dame of Chicago’s theatre scene. Join one of the daytime Historic Theatre Tours for a behind-the-scenes look at the theatre’s architecture and engineering.

The Chicago Theatre’s marquee is one of Chicago’s much-loved and most-Instagrammed icons. You won’t be disappointed once you’re Inside the theatre as well. It’s the height of French Baroque grandeur, with a lovely lobby, stately staircase, and majestic ceiling murals. The theatre was America’s first grand movie palace, and became a model for all those after it. Today, you can book tickets for concerts, Broadway shows, musicals, plays, and special performances by today’s leading comedians and entertainers. Stop by in the afternoon for a Chicago Theatre Marquee Tour, and get the inside scoop on the theatre’s history and architecture — and even get a chance to stand on the famous stage.

Insider tip: Architecture buffs won’t want to miss Open House Chicago, a free public festival hosted by the Chicago Architecture Center annually in October. More than 200 architectural treasures and hidden gems open their doors for self-guided tours. Plan your trip today!