Chicago has played a major role in the history of the U.S., so it’s no surprise that the city boasts a rich selection of historical destinations. Explore beautiful turn-of-the-century homes like the Robie and Glessner houses, stroll through Graceland Cemetery, or wander through Lincoln Park during your next tour of the Windy City.

Whether you’re traveling with students, coworkers, or friends, Chicago Charter Bus Company can provide modern charter buses for your group. Give us a call at 312-667-0906 to book a spacious bus with plush seats and air conditioning, and keep reading to discover all of the history-packed spots you can visit in Chicago.

Man in Chicago with buildings in background

Graceland Cemetery and Arboretum

Founded in 1860, Graceland Cemetery serves as a resting place for many Civil War soldiers and Chicago aristocrats. Lawyer Thomas Bryan commissioned H.W.S. Cleveland to design this park-like cemetery on the north side when he realized Chicago’s citizens didn’t have a scenic place to be buried.

Today Graceland Cemetery has a reputation as one of the most beautiful cemeteries in the city, thanks to its ornate architecture and plentiful trees. Make sure your group stops by the Carrie Eliza Getty Tomb, which was designed in 1890 by acclaimed architect Louis Sullivan. Lumber baron Henry Harrison Getty spared no expense to honor his deceased wife, and the Getty Tomb is often considered the most impressive monument in the cemetery.

Address: 4001 N Clark St, Chicago, IL 60613
Charter bus parking: The cemetery has a small parking lot near the main office, but if the lot is full or your bus won’t fit, your driver can park along nearby streets.

Graceland Cemetery mausoleums

Robie House

Frank Lloyd Wright designed this iconic horizontal residence for Frederick Robie in 1906. The building looks like 2 large rectangles sliding past one another and helped establish the Prairie architectural style that Wright later became famous for. You can take a 45-minute guided tour to see the 20-foot cantilevered roof, art-glass windows, and open living room for just $20 per person.

Tours include a maximum of 8 people, though that number may increase when social distancing protocols aren’t in place. The exterior and ground floor of the building are accessible to people using mobility devices: however, the second floor can only be reached using stairs.

Address: 5757 S Woodlawn Ave, Chicago, IL 60637
Charter bus parking: Because the Robie House is on the University of Chicago campus, parking is limited. Look for street parking spots or lots that are labeled for visitor use. Your charter bus driver can also drop you off in front of the house before going to find a spot.

Robie House exterior

Image credit: Wikimedia Commons

Lincoln Park

Most tour groups stop by Lincoln Park at some point—in fact, it’s the second most-visited park in the U.S., only behind Central Park. But not everyone realizes just how much history this huge park contains. What is now Lincoln Park started out as a cemetery built in 1843. In 1860, the city converted the cemetery and surrounding greenspace into a public park called Lake Park, and the name was changed to Lincoln Park after Abraham Lincoln was assassinated in 1865.

When the cemetery was turned into a park the city moved most of the graves, but not all of them. Your group can still visit the Couch Crypt, a pre-1860 mausoleum that’s believed to contain the bodies of Ira Couch and his family. You can also stop by the Alfred Caldwell Lily Pond, which is not quite as old but still historic. Originally built in 1889, the pond was redesigned by Alfred Caldwell in the 1930s with funding from the Works Progress Administration.

Address: 125 W Fullerton Pkwy, Chicago, IL 60614
Charter bus parking: The Lincoln Park Zoo offers a paid parking lot near the Lily Pond. Your bus can drop you off and pick you up at the West Gate, near the corner of Stockton Drive and Webster Avenue.

Lincoln Park lake with skyline in background

Glessner House

Designed by Henry Hobson Richardson in 1887, the Glessner House is one of the oldest still-standing homes in Chicago and has been declared a National Historic Landmark. Richardson decided to make the house feel more welcoming than the typical Victorian home, with less ornate architecture and more open spaces to gather in. His design decisions inspired Louis Sullivan and Frank Lloyd Wright, who would follow his example when creating the Prairie architectural style.

You can only enter the Glessner House by joining a guided tour. Custom tours for groups of up to 8 people are available with at least two weeks’ notice, and your docent can personalize the tour to suit your group’s ages and interests. Unfortunately, the Glessner House isn’t wheelchair-accessible, so the Robie House is a better choice for groups with mobility concerns who want to see a historic home.

Address: 1800 S Prairie Ave, Chicago, IL 60616
Charter bus parking: Your charter bus can park for free along 18th Street or Indiana Avenue. If all of those street parking spots are full, there’s metered parking on Michigan Avenue and a paid lot nearby.

Exterior of Glessner House

Image credit: Wikimedia Commons

Biograph Theatre

The Biograph Theatre was built in 1914 as one of Chicago’s first movie houses. Although it’s now called the Victory Gardens Theatre and hosts live plays, it still has its original features, like a storefront-width lobby, free-standing ticket booth, recessed entrance, and elaborate marquee. Made of red brick and white terra cotta, the building was designed to look respectable so people wouldn’t be embarrassed to go to the movies!

The Biograph Theatre became even more historic when gangster John Dillinger was killed there by FBI agents. Dillinger was attending a movie on July 22, 1934, and FBI agents managed to corner and shoot him in a nearby alleyway. Your group can stop by the theatre alone or as part of a guided gangster history tour to learn more about early movie houses and Dillinger’s death.

Address: 2433 N Lincoln Ave, Chicago, IL 60614
Charter bus parking: The Victory Gardens Theatre offers a parking garage and valet services, but since those options aren’t easy to use with a charter bus, your driver will probably need to find a nearby paid lot.

Biograph Theatre marquee

Image credit: Wikimedia Commons

Jane Addams’ Hull-House Museum

Jane Addams and Ellen Gates Starr founded Hull House in 1889 to give recently arrived immigrants a safe, clean place to live while they learned English, found jobs, and searched for permanent housing. Hull House changed how many Americans viewed immigrants and made Jane Addams the first American woman to win a Nobel Peace Prize. Today, Hull House is a museum that consists of the Hull Home and the Residents Dining Hall.

The exhibits here cover the history of Hull House as well as social justice issues that affect present-day immigrants. The museum is free but asks for a donation of $5 per person, and public tours take place Tuesday through Friday and Sunday at 10 a.m. and 3 p.m. Private tours are also available for groups of 10 or more, though they come with a fee and are not offered while social distancing protocols are in place. When Hull House gets back to running field trips for students, you’ll pay $50 per group of 10. Larger groups will have to split up, and you must have 1 adult chaperone for every 10 students.

Address: 800 S Halsted St, Chicago, IL 60607
Charter bus parking: The Jane Addams’ Hull-House Museum lies on the campus of the University of Illinois at Chicago. Your bus driver will need to search for paid visitor parking on campus.

Hull House from the outside

Image credit: Wikimedia Commons

Wrigley Field

You can’t miss a Cubs game if you’re traveling with a group of sports fans, and Wrigley Field is a great historic stop even for groups who don’t love baseball. Built in 1914, it’s the second-oldest baseball stadium in the MLB, only behind Fenway Park, and it still has its signature manual scoreboard and ivy-covered walls.

Over the years, “The Friendly Confines” have played host to historical moments like Babe Ruth pointing to the bleachers and hitting a home run to where he’d pointed and the Chicago Cubs winning the pennant in 2016. When the Cubs aren’t playing, you can book a 60-minute guided tour for $30 per person that takes you to the visitors’ clubhouse, the Cubs’ dugout, the field, and the private 1914 Club.

Address: 1060 W Addison St, Chicago, IL 60613
Charter bus parking: Wrigley Field has plenty of parking, including a remote lot where your bus can park for free after dropping you off.

Wrigley Field sign welcoming guests

Image credit: Blake Guidry on Unsplash

Explore Chicago’s History on a Charter Bus

If you love history, you’ll love taking a charter bus tour of Chicago. Contact Chicago Charter Bus Company with your itinerary and number of passengers to find out more about the modern, well-appointed buses we can provide for your group. We can help you explore Chicago when you call us at 312-667-0906.