
Photography by Karl Solano
Auditorium Theatre
As the birthplace of the first modern skyscraper, Chicago has been wowing architecture lovers since the late 1800s. Every vantage point—from one of the many rooftop bars that dot the city to the Lakefront Trail that runs near the Shedd Aquarium—offers a new perspective on the iconic skyline. Its modern glass skyscrapers tower over the geometric designs of the Art Deco buildings, which date back to the 1920s. If you want a more up-close look, here are some architectural highlights to add to your next trip, as well as four historic places to stay.

Photography by Jen Roberts
The Rookery building
SEE
The Rookery (1888): Located in the middle of the financial corridor on LaSalle Street, this building is a great example of early skyscrapers. Designed by architects Daniel Burnham and John Root, the ornate details of the 11-story building are reminiscent of medieval-European and Moorish architecture, though it’s the inside that’s the real showstopper. The two-story lobby, which is topped with a glass ceiling, was redesigned by Frank Lloyd Wright in 1905 and completed in 1907. In the redesign, copper-plated ironwork was covered by white marble, and bronze chandeliers were added. You can view the lobby anytime or schedule a tour to see the rest of the building. 209 S. LaSalle.
Auditorium Building (1889): Louis Sullivan and Dankmar Adler designed the building to be a multi-use space, with the main feature being a theater (as the name implies). The goal: to make opera and the arts accessible to everyone. To do so, Sullivan and Adler pushed box seats to the sides of the theater and expanded the main floor. To subsidize the theater costs, a luxury hotel was included in the design. When first erected, the building was one of the largest and heaviest buildings in Chicago. Today, you can tour the building or attend a show in its famous auditorium. 430 S. Michigan.
Chicago Cultural Center (1897): The Chicago Public Library’s first permanent home, the building became a free cultural center in 1991 and offers programs, concerts, and art exhibitions. Inside, the space is decadent, with a large stained-glass Tiffany dome that spans 38 feet in diameter. With approximately 30,000 pieces of glass, it is the largest Tiffany dome in the world. Building tours are offered several times each week. 78 E. Washington.
TO STAY
Chicago Athletic Hotel (1893): Originally built to house an elite men’s club, the building was transformed into a boutique hotel in 2015. The meticulous renovation of this Venetian-inspired building required the hands of more than 1,000 artisans and skilled workers. Today, a Shake Shack sits in what used to be a Turkish bath, and Fairgrounds Coffee & Tea is located in a former cigar area. The grandeur of the original building still remains, though, with a grand stairwell and two lobbies, one of which has leather couches arranged around three working fireplaces. Perched above the famous arched windows sits Cindy’s, a glass-enclosed rooftop bar offering views of Millennium Park. 12 S. Michigan.
Staypineapple (1895): Pet-friendly, individual duvet comforters, and free pineapple-shaped sugar cookies are part of the experience at this hotel, located in the Reliance Building, now a National Historic Landmark. Original details include terrazzo floors, iron filigree staircase railings, marble walls, brass doorknobs (and old-fashioned keys), and exquisite ironwork enclosing the elevators. 1 W. Washington.
Pendry Hotel (1929): The Carbide and Carbon Building, built in 1929, is an architectural gem amid the Chicago skyline—so much so that the city keeps its gold spire lit, a distinction given to only a handful of buildings. The black granite, green terracotta, and bronze trim exterior is topped with a 24-karat gold leaf. The Art Deco details continue inside with Belgian marble and intricate bronze trim. The hotel has 364 contemporary guest rooms and suites that complement the building’s gilded past. 230 N. Michigan.
The Robey Hotel (1929): Located in what was formerly called Northwest Tower (and the Coyote building) in the trendy Wicker Park neighborhood, this 12-story building is one of the few skyscrapers built outside of downtown Chicago but still offers some of the best views of the city. The building has retained its Art Deco details, including the rooftop spire, which now includes a seating area where you can enjoy a cocktail from the Up Room. Café Robey also serves seasonal comfort food and a creative cocktail menu on the first floor. 2018 W. North.
TOUR
The Chicago Architecture Foundation Center offers a 90-minute architecture river cruise that is operated by Chicago’s First Lady and not to be missed. The cruise is led by a volunteer docent who shares stories and the history behind more than 50 of Chicago’s most famous buildings, including the Wrigley Building, Tribune Tower, TheMART, Marina City, Aqua Tower, the John Hancock Center, and Willis Tower (formerly known as Sears Tower). And if you can visit Chicago in October, be sure to check out the month-long architectural open house.