The 15 best places to dive deep into Chicago's history

Founded in 1837, the city of Chicago is bustling with history and culture. From daring architecture to landmark music venues, there’s no shortage of must-visit historical sites to see on your next trip to the Windy City. As a bonus, many of them are free to visit.

If you’re traveling to Chicago, be sure to add these famous, historic landmarks to your list of things to do in the city. 

1. DuSable Home

Chicago’s founder was a Black man named Jean Baptiste Point DuSable, who scholars think was born in Haiti. He arrived here with his Potawatomi wife around 1779, and built a trading post and farm along the Chicago River at the spot known today as Pioneer Court, abutting DuSable Bridge. A bronze bust marks the spot where his cabin stood. 

DuSable was a respected entrepreneur who prospered at a time of prejudice and oppression. He spoke English, French, Spanish and several Native American dialects and did business with all types of people. In 1800 he sold the property and moved downstate, but it was from his farm that Chicago sprouted.

Planning tip: Once you’ve visited the site of DuSable’s house, you can learn more about Black history in Chicago at The DuSable Black History Museum and Education Center in Washington Park.

2. Graceland Cemetery

Founded in 1860, Graceland Cemetery is the final resting place for many of Chicago’s most notable citizens. The city decided to stop using Lincoln Park as the public burial ground for health reasons, so Graceland became the main graveyard. 

It’s nicknamed the “cemetery of architects,” and folks like Daniel Burnham (designer of the 1893 Chicago World’s Fair) and Fazlur Khan (the engineer behind the Willis Tower) catch their eternal zzz’s here. Cyrus McCormick, whose factory sparked the Haymarket riot, and Union Stockyards meatpacking magnate Philip Armour both lie here too.

For the sports-inclined, baseball player Ernie Banks – aka “Mr Cub” – is interred at Graceland in a nifty tomb, as is William Hulbert, one of the founders of the National League.

Planning tip: While the cemetery is open year-round, it closes by 4pm or 6pm depending on the day of the week and the season. Be sure to check the hours before you visit.

3. Union Stockyards

The Union Stockyards opened on the South Side in 1865, and thanks to Chicago’s central location, rail network and the abundance of cheap immigrant labor, this quickly became the world’s meat-processing hub. 

Millions of pigs and cows trundled through the still-standing Stockyards Gate each year to meet their demise in the slaughterhouses and some 40,000 people worked here at the height of the action in the 1920s. 

Conditions for workers were terrible, with long hours, low wages and a dangerous, unsanitary working environment. Exposés by writers such as Upton Sinclair led to labor reforms eventually, and these had a national impact. The stockyards closed in 1971, but it’s worth dropping by to ponder the site’s long history.

4. Chicago Water Tower

The 154ft-tall, turreted Chicago Water Tower is a defining city icon. After the Great Chicago Fire ripped through town in October 1871, torching more than 17,000 buildings – pretty much the entire inner city – the Water Tower was one of the few structures left standing. 

This was due partly to its yellow limestone bricks, which withstood the flames, but also due to the quick thinking of firefighter Frank Trautman, who soaked blankets and sails in lake water and covered parts of the building. 

Built in 1869 in an eye-popping Gothic style, the tower went on to become a motivating symbol for a city that would rise from the ashes.

Planning tip: In the same area, you can visit the 360 Chicago observation deck at the John Hancock Center, and the Museum of Contemporary Art. 

5. Haymarket Square

On May 4, 1886, a deadly riot at Haymarket Square ignited the world’s labor movement. In the days leading up to the riot, workers at factories, including the McCormick Harvesting Machine Works, went on strike fighting for an eight-hour working day, rattling the factories' powerful owners.

Workers planned a rally at Haymarket Square, which began peacefully but turned violent when police intervened. An unknown person – unidentified to this day – threw a bomb that exploded and killed seven officers. The government responded harshly, convicting eight anarchists and executing four. 

This violent crackdown on labor activists ultimately brought international attention to the plight of workers. A sculpture marks the square today; it’s a thought-provoking spot to consider the fight for workers’ rights.

6. Monadnock Building

Architecture buffs go gaga at the Monadnock because it’s two skyscrapers in one, marking a turning point in high-rise evolution. The northern half (from 1891) is older and plainer, since architects Burnham & Root used thick, traditional load-bearing walls. 

But Root died, and Holabird & Roche took over to build the southern half in 1893. They used the new metal frame technology that had recently been developed, allowing the outer walls to be thinner and jazzier, with scalloped edges and bigger windows. This latter style went on to revolutionize skyscraper design.

Planning tip: The Monadnock Building is just a block from Jackson subway station, within easy walking distance of the Art Institute and Grant Park.

7. Jackson Park

This 550-acre green space on the lakefront hosted the legendary 1893 Chicago World’s Fair. The event was centered on a grand complex of specially built structures painted white and brilliantly lit by electric searchlights, earning it the nickname the “White City.” 

Designed by architectural luminaries such as Daniel Burnham and Frederick Law Olmsted, the fairgrounds were intended to show how parks, streets and buildings could be designed in a harmonious manner to enrich the chaotic urban environment. 

Open for only five months, the exposition attracted 27 million visitors, many of whom rode the newly built L train from the Loop. The fair put Chicago on the map as a city of big ideas. Today, Jackson Park is a relaxing place to stroll beside Lake Michigan, taking in the views.

Planning tip: Be sure to visit the Griffin Museum of Science & Industry, the city’s premier science museum, at the north end of the park. Modified over the years, it's one of the last surviving structures from the World's Fair.

8. Grant Park

Chicago’s “front yard,” Grant Park is one of the oldest landmarks in the city and it was the subject of many legal fights. While forward-thinking locals lobbied to have the lakefront green space protected back in 1835, city commissioners wavered on the idea for 55 years, before they approved plans for civic buildings to go up here. 

However, retail magnate A Montgomery Ward said nope, the downtown park should remain an open public space with no obstructions to the views of Lake Michigan. He took the city to court multiple times between 1890 and 1911, when he finally won the right for Grant Park to remain “forever open, clear and free.”  Today, it’s a place to walk, skateboard, play baseball, and take in big events.

Planning tip: Book tickets, flight and accommodation in advance if you come to Grant Park to see big-name events such as the Taste of Chicago, Blues Fest or Lollapalooza. 

9. Bronzeville

Bronzeville is the historic heart of Chicago’s Black arts and culture scene. During the Great Northern Migration – the biggest mass movement in US history – millions of Black people left the South between 1910 and 1970, and some 500,000 of these domestic migrants settled in Chicago. 

The Chicago Defender, a major Black newspaper based in Bronzeville, encouraged this exodus, though arrivals were generally restricted to living in the South Side’s “Black Belt” areas by openly prejudicial real estate practices. Still, Bronzeville thrived as the “Black Metropolis” through the 1950s, with a remarkable jazz, literary and civil rights history that visitors can still catch glimpses of today.

Planning tip: Start your explorations with the Bronzeville Walk of Fame, with nearly 100 brass plaques set into the sidewalk between 25th St and 35th St, celebrating notable Black Chicagoans.

10. Nuclear Energy Sculpture

As WWII raged, Enrico Fermi and a group of fellow scientists began meeting at the University of Chicago in 1942 to work on a secret experiment – to achieve the first controlled nuclear chain reaction. 

On December 2 of that year, they accomplished it. The scene was a dank squash court under the university’s abandoned football stadium. The nuclear reactor was supposed to have been built in a forest preserve 20 miles away, but a labor strike stopped work, so the impatient scientists went ahead and constructed it on campus. 

A bulbous sculpture by Henry Moore marks the site where it all went down. Swing by as part of a visit to the campus of the University of Chicago.

11. Green Mill

The Green Mill jazz club is legendary for its gangster history. During the Prohibition years from 1920 to 1933, the club was a speakeasy that was supposedly part-owned by Jack “Machine Gun” McGurn, a henchman of Al Capone. 

Gangsters, including the boss himself, were frequent customers. They used the tunnels beneath the venue to hide alcohol and to escape from police during raids. Speakeasies like this helped fuel the success of the Chicago mob, which made a fortune dealing in illegal booze. 

The gangster activities ended (Capone went to jail in 1931, and McGurn was murdered in 1936), but the first-rate jazz performances at the Green Mill continue to this day.

Planning tip: If you fancy a night of Chicago jazz, this cash-only establishment doesn’t take reservations and charges a cover at the door; check the calendar on their website for showtimes.

12. Blues Heaven Foundation

In Chicago, no music genre is as iconic as the blues – the electric blues, to be exact. This is the city where Muddy Waters, Howlin’ Wolf and friends first plugged in their amps in the 1950s, and guitar grooves reached new decibel levels. 

Brothers Leonard and Phil Chess knew the sound was unprecedented, and they set up Chess Records to capture it. From 1957 to 1967, everyone from Waters to Bo Diddley, Chuck Berry and the Rolling Stones came to the unassuming building at 2120 S Michigan Ave to record. 

The Blues Heaven Foundation preserves the original studios and stories from the era. Check their website for upcoming live blues sessions.

Planning tip: You can take a tour of the Chess Records building, but you’ll need to request a reservation in advance by email; their website has details.

13. Second City

A group of University of Chicago students began performing intentionally unstructured skits in a campus bar some 65 years ago, and voilà – improv comedy was born. The troupe went on to open Second City Theater in 1959 in Old Town, where their original gag of incorporating audience suggestions into quick-witted comedy became standard stand-up fare. 

Over the years, Second City has produced some of the country’s most capable funny-bone ticklers, including Bill Murray, Stephen Colbert, Tina Fey, Steve Carell and Keegan-Michael Key. The group adopted its tongue-in-cheek name from New Yorker articles mocking Chicago. Book ahead to take in a show when you’re in town.

Planning tip: Tickets for Second City can range in price from as little as $10 to as much as $91 depending on the show. Upcoming shows are listed on the website. 

14. Willis Tower

Arguably the most famous landmark in the Windy City, Chicago’s tallest building, the Willis Tower, was called the Sears Tower when it was completed in 1973. For almost 25 years, it stood proud as the world’s highest skyscraper. 

Engineer Fazlur Khan came up with the design of nine bundled tubes after looking at cigarettes in their pack. It took 2,000 workers three years to build the structure to its record-breaking 1451ft height. The tower became an emblem of the city’s innovation and modernization, especially at a time when downtown was lagging. 

SOM, the local architectural firm that Khan worked for, went on to design many more of the world’s tallest buildings, including the Burj Khalifa in Dubai.

Planning tip: This skyscraper isn’t just about the views – as well as the famous Skydeck, don’t miss the outdoor garden on the 4th floor and the interactive museum on the 2nd floor.

15. Pilsen

Pilsen, a short distance southwest of downtown, has long been a place where new immigrants set down roots after arriving in Chicago. Migrants from Germany and Ireland formed the first wave in the 1840s, drawn by the neighborhood’s cheap rent and location near factories. 

Czechs arrived in the 1870s – they’re the ones who named the neighborhood after a city in their homeland. In the 1960s, Mexican families began moving in and Pilsen soon became the first majority-Latinx community in the city. 

It paved the way for Chicago’s current rich cultural mix, which is 30% Latinx. Pilsen remains a stronghold for the community, with great places to eat and colorful murals along 16th St telling its story.

This article is adapted from an essay written by Karla Zimmerman in Lonely Planet's Chicago guidebook, published January 2025.