Staircase of the Rookery
Chicago, North America, Read About Can't Miss Places

My Top Five Things to Do in Chicago

Chicago has been on my mind lately. In March, we roamed off to Phoenix, Arizona where we saw the Chicago Cubs play baseball and it got me thinking about taking a trip back to Chi-town. Known also as the “Second City” or the “Windy City,” Chicago is an all-around great town. There is much to see and do—take in a Cubs game at historic Wrigley Field, eat at one of the amazing restaurants there (Iron Chef/Top Chef Stephanie Izard has a restaurant), gander at a Tyrannosaurus Rex skeleton, gaze at a Monet, shop the Magnificent Mile, hang out at Navy Pier, or just walk around the city taking in some of the nation’s great architecture and Industrial Age history.

Here are some of my favorite things to do and see when I’m in Chicago:

The Chicago Cultural Center aka the “People’s Palace” is not to be missed. The entrance on the Washington side will take you into the former library—a celebration of learning and humanism. The lobby features a grand Italian Carrara marble staircase with accents of dark green Irish Connemara stone and an arch inscribed in jeweled mosaic with the names of great intellectuals. Everything about the staircase screams that treasures (books) abound here. The staircase opens into Preston Bradley Hall, where people used to receive their books and read them. A dome of Tiffany glass—the largest of its kind—caps the room. Quotations in multiple languages surround the walls. These verses inspire learning and honor the cultural diversity of those who worked and settled Chicago. On the other side of the building is a memorial to the Union soldiers of the Civil War. Dedicated by the Grand Army of the Republic, the hall is somber and sedate. It, too, has a stained glass dome (designed by Healy and Millet), but its hall, decorated in green Vermont marble, is a solemn place meant for thoughtful contemplation of the horrors of war. Spend some time at the Cultural Center, they have neat exhibitions and lots of events (as well as a tourist center).

The Field Museum of Natural History is filled with Egyptian artifacts, dinosaur skeletons, gems, meteors, and cultural items and animals from all over the world. The minute I enter this neo-classical gem, I see my old friend, Sue (who happens to be a Tyrannosaurus Rex), smiling at me with her (still-sharp!) teeth. I love the ancient Egyptian exhibit. Chicago’s university has a great Egyptology department so the museum has some particularly good finds. Since I was a child, I have been fascinated by a cat mummy on display there. The museum’s heritage starts with the 1893 World’s Fair and donations made by prominent citizens who wanted to see a permanent exposition to educate and bring honor to the city. Marshall Field, the retail store magnate, donated a million dollars to start the museum. With additional funds from industrial heavyweights, such as George Pullman and Harlow Higinbotham, the establishment of the museum was assured. Collections were purchased while some were artifacts that had been on display at the World’s Fair. Over a hundred years later, the museum continues to collect items designed to education and delight. Leave at least a couple of hours to explore, because there is a lot to see. If you have children, they will probably find the sights quite exciting as the museum appeals to all ages.

Chicago is a great city to see by foot and I recommend booking a walking tour. I’ve used the Chicago Architecture Foundation in the past and have been quite pleased. They have tours on Chicago’s historic neighborhoods, history skyscrapers, Tiffany treasures, and much more. I went on the “Daniel Burnham: Architect, Planner, Leader” tour which gave great insight into the lead architect of the 1893 World’s Fair, as well as his relationship with his wife, business partner, and professionals. While you’re wandering around Chicago, it’s fun to stop by the Federal Reserve Bank. With its Corinthian colonnade reminiscent of Greek temples, the façade begs the question, “Why do we build temple-like structures for financial institutions?”  Do we worship money? Built in 1922 by Graham, Anderson, Probst, and White, its vault was one of the largest constructed at the time. Visitors can go inside the free “Money Museum” and learn about the Federal Reserve System, see historical currency, and engage with quite interesting interactive exhibits.

Chicago shows off a different side from the water and I highly recommend seeing it from the river. Several companies, including the Chicago Architecture Foundation, offer water tours of the city, but if you’re looking to save a little money, water taxis are an affordable way to see Chicago from the water. I’ve used Shoreline before, which I liked because their boats have a nice open part that allows for great sightseeing and picture-taking. Their boats have a river route they take visitors on, as well as a lake route that goes from Navy Pier to the Museum Campus (Shedd Aquarium, Field Museum, and Adler Planetarium).

I am quite in love with the Driehaus mansion—this stately residence pays tribute to Gilded Age America. Its finishings scream “wealthy people once lived here.” Looking at the architecture, design, furniture, and objets d’art, it’s easy to see why this era is dubbed gilded. The mansion seems kissed with gold. From its intricately-carved wood pocket doors to its parquet floors, the 1880s home of banker Samuel Nickerson feels rich. Now a museum, visitors can explore its three floors, which have a nice collection of Tiffany decorations, period furniture, paintings, and rotating exhibits (they had one on art jewelry when I was there). Ask the guide to let you see where the servants quarters were located for a Downton Abby upstairs/downstairs experience. As you explore the mansion, think about how the nouveau riche used their homes as an expression of their financial prowess. Revel in the contradiction between various styles of architecture—all chosen to express grandeur. Bring comfortable shoes because those marble floors can wreak havoc on the back!

Although Chicago has much more to see and do, lastly I suggest visiting the Art Institute of Chicago for yet another feast of the senses. The institute has an impressive collection of Impressionist art, as well as notable ancient artifacts, the famed American Gothic by Grant Wood, and over 3500 European works dating from the 12th through the mid-20th century. The building traces its roots to the 1893 World’s Fair and is an impressive artifact in itself.

Chicago is a culturally-rich city with its heritage honored many places throughout the town. Its food offerings are renowned. Take a walk in Millennium Park and enjoy the outdoor art installations. For a carnival-like feel, journey down to Navy Pier and ride the Ferris Wheel (first debuted at the 1893 Chicago World’s Fair). Enjoy some shopping while looking at fin de siècle architecture. Don’t forget to try the ridiculously filling deep-dish pizza. Putting the “pie” in pizza pie, it’s something everyone should try at least once in their life. The Windy City has great entertainment to offer, too—the Cubs, Hamilton, and the Second City comedy troupe among others. I hope you enjoy all the fun things to do in Chicago. Happy travels!

Like what you just read? You can support me by following my blog and leaving comments–I love to hear from my readers. Amy

If you enjoy our pictures, please check out our photography shop on Etsy where you can purchase our prints. We don’t have all of our prints listed on our Etsy site, so don’t hesitate to contact us if you see a picture in a blog post that you would like to order.


Leave a comment for the Roaming Historian

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.