Architecture buffs and laypeople alike will revel in the design of the Loop’s towering buildings. The structures found in this area represent a variety of important and influential historical styles, from the rounded arches and thick walls of Richardsonian Romanesque (1870–1900) to the stark simplicity and functionalism of International Style (1932–45). These buildings were the blueprints for many similar structures in North America.

START: Wacker Drive in front of the Civic Opera House. El: Brown Line to Washington Station

1. Willis Tower

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The skyscraper formerly known as the Sears Tower (naming rights were sold to London-based insurance broker Willis Group in 2009) is 110 stories and was the tallest building in the world when it opened in 1973. Today, it proclaims itself the tallest building in the Western Hemisphere (One World Trade Center in New York City disagrees, and the technicality revolves around an antenna). Yet, more than 45 years since it was built, it’s still a marvel of engineering, which you’ll get a deeper understanding of as you wind your way through the building, passing a series of museum-style exhibits that put the height into context (like, how many of you need to be stacked to reach the top of Willis Tower?). The 60-second elevator ride to The Skydeck on the 103rd floor flies by, and then, lo and behold, breathtaking views of four states unfold. If you dare, step onto The Ledge, a series of observation boxes that jut out from the building. There’s nothing between you and the ground but a layer of glass. Your best bet to beat the crowds is just after it opens or around 5pm.

Time: 1 1/2 hrs. 233 S. Wacker Dr. (enter on Jackson Blvd.). tel. 312/875-9696. www.theskydeck.com. Admission $24 adults, $16 seniors and children 3–11, free for children 2 and under; Fast Pass $49 (allows you to bypass the line, which may be 2 hrs. during busiest times). Mar–Sept daily 9am–10pm; Oct–Feb daily 10am–8pm. El: Brown, Purple, or Orange line to Quincy, or Red or Blue line to Jackson; and then walk a few blocks west.

2. Civic Opera Building

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Fronting the broad roadway of Wacker Drive (named after Charles Wacker, a civic-minded brewer and a director of the World’s Columbian Exposition of 1893), this Art Deco/French Renaissance building was completed in 1929. Utility magnate Samuel Insull, the president of the Chicago Civic Opera Association in the '20s, installed a 3,500-seat opera house and a 900-seat theater in this 45-story office building so the property’s commercial rents would subsidize the arts. The Grand Foyer of the opera house, with its 40-foot-high ceiling and gold leaf–topped marble columns, is worth a peek when the building is open, if you can swing it, or check the website of the Lyric Opera—the resident of the house—for backstage tours, which are offered throughout the year for $15.

Time: 5 min. 20 N. Wacker Dr. tel. 312/827-5600. www.lyricopera.org. El: Brown Line to Washington.

3. 333 W. Wacker Dr.

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The green-hued facade of this 36-story building reflects the Chicago River like a massive looking glass. The postmodern structure was designed to blend with its surroundings, and the curved exterior artfully echoes the curve in the river. Indeed, the best way to view this building is from the river (you’ll be able to experience this on an architectural river tour). Designed by Kohn Pedersen Fox in 1983, the building was squeezed onto a triangular lot that was previously thought suitable only for a parking lot. Another good vantage point for viewing the edifice is from the Franklin Street Bridge.

Time: 5 min. 333 W. Wacker Dr. (at Lake St.). El: Brown, Purple, or Orange line to Washington.

4. The Merchandise Mart

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Staking its claim as the world’s largest commercial building, this 2-city-block Art Deco structure was built by Marshall Field as a wholesale emporium and completed in 1931. If you view the building from across the river, you’ll see a line of pillars upon which rest oversize busts of the icons of American merchandising, including Marshall Field, Edward A. Filene, Frank Winfield Woolworth, Julius Rosenwald (Sears), and Aaron Montgomery Ward; the busts were commissioned by former owner Joseph Kennedy, of the politically famous Kennedy clan. Most of the Mart is open to designers and trade show goers, but the public can explore Luxe Home on the ground floor, with its eye-popping array of high-end home decorating shops.

Time: 15 min. 222 W. Merchandise Mart Plaza. www.merchandisemart.com. El: Brown Line to Merchandise Mart.

5. The James R. Thompson Center

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Chicagoans still refer to this cascading glass-and-steel building—the work of celebrated contemporary architect Helmut Jahn—by its original name, the State of Illinois building. That’s fitting, as the 16-story structure houses the Chicago branches of the state government. The glass walls that enclose the offices are said to be a symbolic reference to “open government.” For spectacular views, ride the glass elevator to the top, though this will not be a pleasant experience for anyone afraid of heights.

Time: 10 min. 100 W. Randolph St. (at LaSalle St.). www2.illinois.gov. tel. 312/814-9600. El: Brown Line to Clark/Lake.

6. City Hall/County Building

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This landmark Classical Revival building, dating back to 1911, is composed of two sections: City Hall fronts LaSalle Street on the western side, and The County Building, the older and more classically inspired edifice, faces Clark Street on the east. The county section’s exterior, with its 75-foot Corinthian columns, is the more notable of the two, designed in part by one of Chicago’s legendary architectural firms, Holabird & Roche. The public meetings of the Chicago City Council, held in the council chambers of City Hall, are dramatic enough to be worth a visit for policy wonks. Call ahead to find out when the council is in session.

Time:  10 min. 121 N. LaSalle St. tel. 312/742-5375. www.chicityclerk.com. El: Brown Line to Washington.

7. Rookery Building

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This relic of Old Chicago, completed in 1888, was named for a demolished city hall building that once stood on this site—the roost of many pigeons and politicians. The rough granite base and turrets show the influence of the heavy Romanesque style of H. H. Richardson. Venetian and Moorish influences are evident on the exterior. I wholly recommend seeing the open interior court (designed by Frank Lloyd Wright), which rises to the full height of the landmark building’s 11 stories. The ornately decorated space was constructed from iron, copper, marble, glass, and terra-cotta.

Time: 15 min. 209 S. LaSalle St. www.therookerybuilding.com. El: Brown Line to Quincy. 

8. Chicago Board of Trade

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It once housed the raucous economic free-for-all that was the world’s largest commodities exchange, until open outcry trading started going the way of the ghost, replaced by computer screens (Chicago Board of Trade merged with Chicago Mercantile Exchange in 2007, forming CME Group, which is now headquartered about a mile north). Still, this streamlined Art Deco building is one of the best examples of that style in the city. Along the landmark building’s rear wall, a postmodern addition by Helmut Jahn offers a repetition of the pyramid-shaped roof. The statue of the Roman goddess Ceres on the top of the 45-floor structure strikes a quirky architectural note—she was left faceless because the designers figured nobody would get close enough to see her features. Due to security restrictions, this one is best viewed from the sidewalk.

Time:  5 min. 141 W. Jackson Blvd. www.141wjackson.com. El: Blue Line to Jackson/Dearborn.

9. Monadnock Block

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This significant block actually consists of two buildings, built 2 years apart using two very different construction methods. Monadnock I, on the northern end, was built by Burnham and Root between 1889 and 1891, with deeply recessed windows at street level, encased by walls up to 8-feet thick. It was the last skyscraper in the United States to use this method of construction. Monadnock II, built by Holabird & Roche in 1893, is one of the country’s first steel-framed buildings, but is noteworthy in that it maintains a continuity of style with Monadnock I.

Time:  10 min. 53 W. Jackson Blvd. El: Blue Line to Jackson/Dearborn.

10. Marquette Building

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Named for Jacques Marquette, a French Jesuit explorer who was one of the first Europeans to record the existence of the area now known as Chicago, this 1895 building was one of the country’s first commercial skyscrapers. The marble lobby, which is worth seeing, commemorates the spirit of exploration with a series of explorer-themed relief sculptures and Tiffany windows.

Time: 10 min. 56 W. Adams St. El: Blue Line to Jackson/Dearborn.

11. Reliance Building (The Alise Chicago)

This prototype of the modern skyscraper was made possible by the development of high-speed elevators and steel framing. The terra-cotta and glass facade gives the 1895 building a modern appearance. Its window design—a large central pane of glass flanked by two smaller, double-hung windows for ventilation—eventually became known as the Chicago Window. It’s now home to a hotel called the Alise. The rooms all have doors that are a throwback to the days when this was an office building for the likes of Al Capone’s dentist. Ask at the front desk if you can take a peek.

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Time: 5 min. 1 W. Washington St. (at State St.). tel. 312/940-7997. www.staypineapple.com. El: Red Line to Washington.

12. Take a Break: Latinicity is a festive food hall by celeb Chef Richard Sandoval, where all the offerings, including tacos, soups, sandwiches, seafood, and more, have one thing in common: ties to the Latin world. Block 37, 3rd floor, 108 N. State St. tel. 312/795-4444. www.latinicity.com. $–$$. 

13. North Loop Theater District. This row of renovated historic theaters along Randolph Street was a longtime dream of city planners, and on this short tour you’ll see why: Their colorful, glitzy facades and over-the-top decor give each a unique character. The Versailles-inspired Cadillac Palace Theatre is a former movie palace that now hosts touring musicals, dance performances, and concerts. Another former movie palace, the spectacular Ford Center for the Performing Arts Oriental Theatre opened in 1926 and was restored in the 1980s to its original, over-the-top Indian-inspired decor. Marked by a nostalgic orange-lettered marquee, the landmark Chicago Theatre is the oldest Beaux Arts building in the city. The 3,800-seat hall opened in 1928 and was restored in 1986 as a showplace for Broadway musicals, concerts, and dramas. All three theaters use a number run by Broadway in Chicago (tel. 312/977-1700). Home of the city’s oldest resident theater company, the Goodman Theatre opened in 2000, incorporating the landmark neo-Georgian and Palladian facades of the old Harris and Selwyn theaters. The facility includes 850- and 400-seat theaters (tel. 312/443-3800; www.goodmantheatre.org). The large bar at Petterino’s (150 N. Dearborn St.; tel. 312/422-0150; www.petterinos.com; $$) is an ideal place to dine at the end of a long day of walking or before a show. The menu is old school—wedge salad, chopped steak, salmon cakes—but done well. Some dishes are named after local celebrities. Take the Irv Kupcinet, for example, a popular salad of chopped minced greens and blue cheese named for the longtime Sun-Times columnist.

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Time: 1 hr. El: Blue or Brown line to Clark/Lake.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.