12 Best Sights in Chicago, Illinois

Named one of the 10 most significant buildings of the 20th century by the American Institute of Architects, the 9,063-square-foot Robie House (1910) is long and low. Massive overhangs shoot out from the low-pitched roof, and windows run along the facade in a glittering stretch. Inside, Wright's "open plan" echoes the great outdoors, as one space flows into another, while sunlight streaming through decorative leaded windows bathes the rooms in patterns. The original dining room had a table with lanterns at each corner, giving the illusion that the table itself was a separate room. Other Wright innovations include a three-car garage (now the gift shop), an intercom, and a central vacuum-cleaner system.

This 1951 minimalist dwelling by Ludwig Mies Van der Rohe sits just down the Fox River from Aurora. Constructed of steel, wood, and travertine marble, it appears to nearly float against a backdrop of serene river views and woodland landscapes. Now operated as a museum by the National Trust for Historic Preservation, Farnsworth House may only be seen by guided tour (advance reservations are required). Note that the house is a half-mile walk from the visitor center.

Wright designed and built his first home in 1889, on the strength of a $5,000 loan from his then employer and mentor, seminal Chicago architect Louis Sullivan. Only 22 at the time, he would continually remodel the modest dwelling over the next two decades, so a visit here provides a unique look into the architect's developing ideas. This is where Wright's nascent architectural philosophy first bloomed; the house was intended not only to hold his rapidly growing family, but also to showcase his then-revolutionary notions. It combines elements of the 19th-century Shingle Style with subtle innovations that stamp its originality.

Wright established his own practice in 1893 and added a studio to the house in 1898. In 1909, he spread his innovative designs across the United States and abroad (at this time he also abandoned his wife and six children for the wife of a client). He sold his home and studio in 1925, which was later turned into apartments that eventually fell into disrepair. In 1974, a group of local citizens calling itself the Frank Lloyd Wright Home and Studio Foundation, together with the National Trust for Historic Preservation, embarked on a 13-year restoration that returned the building to its 1909 appearance. Today, Wright's Oak Park home and studio are owned by the Frank Lloyd Wright Trust.

Wright's home, made of brick and dark shingles, is filled with earth-toned spaces. The architect's determination to create an integrated environment prompted him to design the natural wood furniture as well—though his apparent lack of regard for comfort is often the subject of commentary. The lead windows have colored-glass designs, and several rooms have skylights or other indirect lighting. A spacious barrel-vaulted playroom on the second floor includes a hidden piano for the children's theatrical productions. The adjacent studio is made up of four spaces—an office, a large reception room, an octagonal library, and an octagonal drafting room that uses a chain harness system rather than traditional beams to support its balcony, roof, and walls.

To see the interior, you must take one of the small-group tours, led by well-informed guides who discuss the architecture, point out artifacts from the family's life, and tell amusing stories about the rambunctious Wright clan. Reservations are advised: without one, you'll need to arrive as early as possible to snag a spot—not later than early afternoon to make the last tour on any given day. Tours begin at the Frank Lloyd Wright Home and Studio Museum Shop, which carries architecture-related books and gifts. You can pick up a map noting other examples of Wright's work that are within easy walking or driving distance; guided tours and self-guided audio ones of the neighborhood are also available.

The annual Wright Plus Architectural Housewalk on the third Saturday in May offers interior tours of private homes designed by Wright and his contemporaries in Oak Park and other nearby villages.

This fortresslike residence is the only surviving building in Chicago by architect H.H. Richardson, who also designed Boston's Trinity Church. Completed in 1887, the L-shaped mansion's stone construction and short towers are characteristic of the Richardsonian Romanesque Revival style. It's also one of the few great mansions left on Prairie Avenue, once home to such heavy hitters as retailer Marshall Field and meatpacking magnate Philip Armour. The area has lately seen the arrival of new, high-end construction, but nothing beats a tour of Glessner House, a remarkable relic of the days when merchant princes really lived like royalty. Enjoy the lavish interiors and the many artifacts, from silver pieces and art glass to antique ceramics and Isaac Scott carvings and furnishings. Guided tours run Wednesday, Friday, and Saturday year-round.

The 500-acre estate of former Chicago Tribune editor and publisher Robert McCormick (1880–1955) has multiple attractions. For starters, there's the First Division Museum, an impressive military history museum that has interactive, immersive exhibits. The sweeping landscape also incorporates formal gardens, picnic grounds, walking trails, and its own 27-hole public golf course with a separate 9-hole course for kids.

Designed by Louis Sullivan and his protégé Frank Lloyd Wright, this almost austere residence is one of the few extant buildings that displays the combined talents of these two architectural innovators. Historians still squabble about who contributed what here, but it's easy to imagine that the young go-getter had a hand in the cleanly rendered interior. Note how the geometric exterior looks unmistakably modern next to its traditional neighbors. Public tours of both the interior and exterior are available and last about one hour. The complimentary Wednesday tours are less comprehensive than the paid ones on Saturday; reservations are required for all tours. Check the website for reservations and pricing.

This Greek Revival structure dates from 1836, making it Chicago's oldest surviving building. It's a clapboard house in a masonry city, built for Henry and Caroline Palmer Clarke to remind them of the East Coast they left behind. The Doric columns and pilasters were an attempt to civilize Chicago's frontier image, while the everyday objects and furnishings inside evoke a typical 1850s–60s middle-class home. The house has been moved three times from its original location on Michigan Avenue between 16th and 17th streets: the last time, in 1977, it had to be hoisted above the nearby elevated train tracks. In 2022, the house was renamed to affirm the profound role of Bishop Louis Henry and Margaret Ford in preserving the house as a significant part of Chicago’s history.

Part of the literary legacy of Oak Park, this three-story, turreted Queen Anne Victorian, which stands in frilly contrast to the many streamlined Prairie-style homes elsewhere in the neighborhood, contains period-furnished rooms and many photos and artifacts pertaining to Hemingway's early life. Museum curators have restored rooms to faithfully depict the house as it looked at the turn of the 20th century. You can poke your head inside the one in which the author was born on July 21, 1899.

When he designed this house in 1896, Frank Lloyd Wright was still moving toward the mature Prairie style achieved in the Robie House 13 years later. As was common with Wright's designs, Heller House is entered from the side. But rather than being long and low, this one has three floors, the uppermost one of which comes complete with pillars and sculptured nymphs. The building is not open to the public.

Samuel Insull, partner of Thomas Edison and founder of Commonwealth Edison, built this mansion as a country home in 1916. After Insull lost his fortune, John Cuneo Sr., the printing-press magnate, bought the estate and fashioned it to suit his own taste. The skylighted great hall in the main house resembles the open central courtyard of an Italian palazzo, the private family chapel has stained-glass windows, and a gilded grand piano graces the ballroom.

Curious about how the wealthy built their urban palaces during America's Gilded Age? Steps away from the Magnificent Mile, the former Samuel Mayo Nickerson mansion has lavish interiors with 19th-century furniture and objets d'art, including pieces by Louis Comfort Tiffany and George Schastey, along with rotating exhibitions related to art, architecture, and design.

At the intersection of Calumet Avenue and Cullerton Street is another of the area's great mansions, which was nearly replaced by a parking lot before it was saved and painstakingly restored in the late 1990s. Today it's a boutique hotel with the same name.