Best Historic Sites in Chicago

Wanted dead or alive: Chicago historic sites from crypts to culture

It wasn't too awfully long ago that people from other countries associated Chicago with Al Capone and later those "Lovable Losers," the Chicago Cubs. By the 1990's, one Michael Jordan put Chicago on the map for his glorious ways with a basketball, and more recently, the curse of the billy goat was flounced when the Cubs finally won the World Series. The losing is behind Chi but you can still experience one of the very few historic ballparks in the country at Wrigley Field.  

Illustrious citizens in the city's past include the formidable Jane Addams  whose work changed international and national public policy in a time when women were to be seen and not heard; George M. Pullman, President of Pullman's Palace Car Company, who created a model neighborhood  for his factory workers; and Frank Lloyd Wright, who needs no introduction but it's good to remind that his Robie House is a masterpiece of Prairie style architecture. Take the opportunity to visit the Chicago Cultural Center for a landmark that is anything but stuffy. 


Chicago claims one of the country's legendary Victorian graveyards. Many of Graceland's tombs are artistically and architecturally renowned and embrace the remains of more than a few famous Chicago characters including Marshall Field, George Pullman, Ludwig Mies van der Rohe, and Potter and Bertha Palmer (who had her chef invent the brownie at the Palmer House). These dead would be grateful to know that visitors regularly stroll the grounds to identify famous gravesites including public figures, baseball and boxing greats, merchants and inventors. The grounds were designed in 1861 by prominent landscape architect H.W.S. Cleveland who aimed to create a park-like ambiance. Another landscape architect, Ossian Simonds, added native plants to create the cemetery's pastoral landscape, making the "Cemetery of Architects" one of the most beautiful places in Chicago to visit.

Recommended for Historic Sites because: The cemetery has been an "Oasis of Art, Architecture, and Landscape Design since 1860."

Jacky's expert tip: Stop at the office, near the historic entrance, for free, self-guided theme tours through Graceland Cemetery.

Read more about Graceland Cemetery →

Frank Lloyd Wright made his enduring mark in the Chicago area where he lived and worked for the first 20 years of his career. The Hyde Park neighborhood is home to Wright's masterpiece, the Frederick C. Robie House, one of the best examples of the visionary architect's organic Prairie-style design. Robie House boasts characteristic horizontal lines, stained-glass windows, earthy tones and balconies. Apparently Wright was an eco-friendly architect since he designed the rooms to be energy efficient by keeping out direct sunlight yet allowing enough light in to keep rooms from growing too dark. The concept was radical and inspired for 1910, and it's still packing in the tourists and design buffs.

Recommended for Historic Sites because: Wright's architectural approach was radical for its time and the Frederick C. Robie House is a magnificent example of the open, flowing and freeing design.

Jacky's expert tip: Take some time to explore Hyde Park's diverse dining scene.

Read more about Robie House →

Lincoln Park

Life long Chicagoans have no doubt passed the spooky, weathered mausoleum in Lincoln Park with the one-word inscription, "COUCH." Ostensibly, it holds the remains of one Ira Couch, because, after all, Lincoln Park used to be the site of City Cemetery. Sealed for more than a century, the crypt may be the final resting place of Ira (who died in 1857), up to eight family members or no one at all. The Great Chicago Fire of 1871 destroyed official records. It's all a mystery, especially why this lone home for the dead remains in the otherwise bucolic Lincoln Park. The crypt cost $7,000 to build back then, a mere pittance of the fortune that Couch made in Chicago real estate and hotels. The 50-ton crypt was designed by John M. Van Osdel. Chicago's first professional architect, who also designed the first City Hall and Couch's 1850 Tremont House Hotel.

Recommended for Historic Sites because: Every Chicagoan who died between 1842-1866 was buried in City Cemetery (now Lincoln Park) including thousands of Union and Confederate Civil War soldiers.

Jacky's expert tip: The tomb is on a grassy knoll in Lincoln Park, just south of LaSalle Drive.

Read more about Couch Crypt →


Open since 1925, Union Station remains Chicago's intercity rail terminal and the largest terminal for commuter trains. The facility cost $75 million dollars to build - more than $1 billion in today's dollars- with an exterior of Indiana Bedford limestone. The station's Great Hall is a peek into America's past and the architectural beauty of a bygone era with its barrel-vaulted skylight flooding the space with soft light, long wooden benches, Corinthian columns and bronze accents. The skylight was blacked-out during World War II to be less of a target as 100,000 passengers passed through daily. Film and television routinely discover the Great Hall (most famously My Best Friend's Wedding, ER and a scene in the movie, "The Untouchables") and countless selfies are snapped on the recently restored grand staircase.

Recommended for Historic Sites because: Union Station is one of America's historic rail stations and an icon of a great age.

Jacky's expert tip: The Chicago History Museum and Chicago Architecture Foundation offer fascinating tours.

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The Glessner House was designed by Henry Hobson Richardson, an architect whose work inspired Louis Sullivan, Mies van der Rohe and Frank Lloyd Wright. The architect collaborated with John Glessner to design a home symbolizing happy family life, a departure from Gilded Age castle-like structures that the country's newly rich industrialists preferred. Both modern and medieval, H. H. Richardson created a integrated environment that Wright would later emulate. You won't see cavernous empty spaces but rooms asymmetrically connected to each other. The house has been painstakingly restored and preserved and includes an outstanding collection of 19th and 20th century furniture and decorative art. The home holds a vast assortment of pieces from the Aesthetic and English Arts and Crafts movements. The collection includes ceramic vases and tiles, silver, engravings, and Art Nouveau glass. Tours are Wed.-Sun. at 11:30 a.m., 1:00 p.m., and 2:30 p.m.

Recommended for Historic Sites because: A National Historic Landmark, Glessner House is an internationally-known architectural treasure.

Jacky's expert tip: Stroll the entire Prairie Avenue District, a historic district that was the site of the Battle of Fort Dearborn.

Read more about Glessner House →


The Chicago Water Tower, built in 1869, is certainly a fairy tale design for something that was merely dressing for a 135 foot iron standpipe. Not only pretty and rather mysterious in a Gothic Revival way, the old gal survived the great Chicago fire of 1871. It's legend that the Water Tower was the only building left standing after the fire. Much of the south and west sides were intact, however, the Water Tower's castle-like looks helped it become a symbol for Chicago rising from its ashes. The Water Tower and pumping station across the street were designed by William Boyington and constructed from blond Joliet limestone. One of the city's most familiar landmarks, the building is now home to City Gallery showcasing the work of local artists.

Recommended for Historic Sites because: The Water Tower was chosen by the American Water Works Association as the first American Water Landmark in the US.

Jacky's expert tip: Although the Tower gets all the drama with regard to the fire, you can still see char marks on the bell tower of St. James Cathedral at Wabash and Huron.

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As the current Zeitgeist mulls immigration, a stop at the Jane Addams Hull House Museum may serve us well. Hull House was a Near West Side settlement house co-founded in 1889 by Jane Addams and Ellen Gates Starr open to newly arrived European immigrants. Italian, Irish, German, Greek, Russian, Polish, African American and Mexican immigrants were able to put down roots and enjoy day care for children of working mothers; an employment bureau; art gallery and library, cultural events and English and citizenship classes. In a time when people are lauded for Instagram photos of their vacations, learning about this remarkable woman who forged a powerful reform movement that helped children, women, union workers and minorities is nothing if not humbling. The museum that honors Addams, the first American woman to receive the Nobel Peace Prize, and her influence on civil rights and women's suffrage includes documents, furniture, photographs and artifacts.

Recommended for Historic Sites because: The museum is a dynamic memorial to a social reformer whose work changed the lives of immigrants and national and international public policy.

Jacky's expert tip: There are self-guided and guided tours of the exhibits which are suitable for all age groups, from elementary school students through adults.

Read more about Jane Addams Hull-House Museum →

Even though there's a fancy hotel, shiny retail and a multi-use outdoor plaza being constructed at and near Wrigley Field, the historic stadium retains its old timey friendly atmosphere for fans of the beloved Chicago Cubs. Don't be too down trodden about the high-definition Jumbotron and renovations - they're primarily structural improvements and the creation of club levels and suites for those who drink and yammer more than actually watch the game. First opened in 1914 as Weeghman Park, home of the Whales, Wrigley still boasts its ivy-covered brick walls in the outfield and a manual scoreboard lending a good-old-days ambience (one of only two left in MLB). Although the days of $1 bleacher tickets are long gone, the spirits of Santo, Banks and Brickhouse permeate the place. Tours, on days they're scheduled, are 75-90 minutes and non-gameday tours include peeks at the Cubs' dugout and the clubhouse.

Recommended for Historic Sites because: It's more than a century old with an 80-plus year-old manual scoreboard and home to everyone's favorite team (unless you're from the south side).

Jacky's expert tip: Don't even think about keeping a home run ball hit by the opposing team - throw it back onto the field.

Read more about Wrigley Field →

Conceived by George M. Pullman, President of Pullman's Palace Car Company, as a model neighborhood for his factory workers, this late 19th-century town originally featured residences, a school, hotel, bank, church, and ahead-of-their-time conveniences like indoor plumbing. Pullman's idea was to attract skilled workers, increase productivity and avoid strikes while insuring better health, a nice environment and uplifted spirit of his employees. Each dwelling had gas and water, access to sanitary facilities and lots of sunlight, fresh air and personal green space as well as access to parks and open land. What a concept! Having survived threats of redevelopment over the last century, the historic district now offers guided tours through the remaining public structures. The magnificent Hotel Florence and the Clock Tower are not to be missed in this incredible neighborhood that welcomes you to back into history.

Recommended for Historic Sites because: The Pullman Historic District was a planned model community for the working class and was voted the world's most perfect town in 1896.

Jacky's expert tip: Named for George's daughter, Florence, the hotel is undergoing a major improvement program by the state to restore it for future use.

Read more about Pullman Historic District →

From 1897 to 1991, the magnificent building served as Chicago's first central public library dazzling visitors with access to knowledge but also two stunning stained-glass domes, intricate mosaics of Favrile glass, mother-of-pearl and colored stone, rich hardwoods and lovely staircases. Bookshelves have been replaced with free wonderful art exhibits, music, dance, theater, panel discussions, films, lectures and family events. It is, however, still home to the world's largest Tiffany stained-glass dome (restored to its original splendor in 2008) so you can get a taste of Chicago history, design (the Beaux Arts style was influenced by the buildings of the 1893 World's Columbian Exposition and its interior rooms were modeled on the Palazzo Vecchio in Florence and the Acropolis in Athens) as well as catch a noon-time jazz concert, see a Keith Haring exhibit or listen to a lecture about Nietzsche and human nature.

Recommended for Historic Sites because: History, beauty and impressive free public events thrill locals and tourists making CCC one of the most visited attractions in town.

Jacky's expert tip: Free building tours take place on Wednesdays, Thursdays, Fridays and Saturdays at 1:15 p.m.

Read more about Chicago Cultural Center →


Meet Jacky Runice

Born in Bucktown when bulletproof was a home safety choice and not a coffee order, Jacky Runice has been knocking around Chicago as a professional print, online and broadcast journalist and...  More About Jacky