Though its ubiquitous nickname is “The Windy City,” Chicago has much more to offer its denizens than just wind and notoriously harsh winters. Chicago boasts a robust culture that makes any visit an exciting and unique experience. From dining to entertainment, activities to architecture, Chicago is a world-class city full of hidden and well-known gems.

Chicago is the United States’ third-largest city, and as would be expected, it has left its stamp on our country’s culture. We see her influence in our daily life—the speakeasy, deep dish pizza, and the idea of multiple hot dog toppings all originate from Chicago.

Good Eats

As any citizen of Chicago will tell you, Chicago makes the best deep-dish pizza in the world. What Chicagoans can’t agree on, however, is which is best. With over two thousand pizzerias in Chicago, it’s pretty obvious why people all have differing opinions. Some of the most well-known pizzerias are Pizzaria Uno’s, Gino’s East, Giordanos, Lou Malnati’s, and Pizanos. They all put their own spin on deep-dish, and all have several locations in and around Chicago. If this seems overwhelming, some instead opt to go on the Original Chicago Pizza Tour, which not only allows interested patrons to sample different kinds of deep-dish pizza, but aims to educate as well.

Another Chicago food staple is the multi-topping’ed Chicago Dog. The most famous eatery to serve this delicacy is Portillo’s Hot Dogs, which is considered a must-visit for any out-of-towner. But truly, the best Chicago Dog can be found at one of Chicago’s most iconic venues: Wrigley Field.

Celebrity chef Rick Bayless also has three restaurants in Chicago, all right next to each other. Xoco, Frontera Grill, and Topolobampo (in order from least to most expensive) all serve signature Mexican-inspired dishes with creative cocktails and farm fresh ingredients.

Another restaurant worth a visit is the Billy Goat Tavern—located beneath Michigan Avenue and forever immortalized by the classic Saturday Night Live “Cheeseburger, Cheeseburger!” skit. In fact, many of SNL’s great talents have come out of Chicago and its Second City comedy troupe, and a trip uptown to see a show is well worth it.

Drink Up

It seems that every city these days has its own special collection of “speakeasy” themed bars, but Chicago pretty much invented the speakeasy. Most notable is Violet Hour, a classy establishment complete with strong cocktails, house rules, low lights and a “secret” entryway behind a mural. Another speakeasy worth checking out is The Office, which requires an exclusive invitation for admittance.

Along with the speakeasy, another Chicago staple is the piano bar. Locals love the Zebra Lounge for its strong martinis, cozy atmosphere, and top-notch live piano music. There is also the famous Davenport’s, which prides itself on being Chicago’s premiere cabaret bar.

A fantastic bar of note is the Signature Lounge, which resides on the 95th floor of the Hancock Tower, one of the tallest buildings in Chicago. They have a fantastic menu in addition to their full bar, but the real reason locals and tourists alike love the lounge is the spectacular view, framed by floor-to-ceiling windows.


One of Chicago’s most defining characteristics is its beautiful skyline, dominated by its largest tower, Willis Tower (formerly the Sears Tower). As the tallest building in the country, its Skydeck is worth a visit to experience the unparalleled view. The Midwest is flat, and from 103 floors up, you can literally see for miles and miles in all directions.

In addition to Willis Tower, Chicago’s buildings are, in general, beautifully built. The city acknowledges this, and the Chicago Architecture Foundation offers an excellent boat tour along the Chicago River to view and learn about all these architectural masterpieces. The boat tours all dock at Navy Pier, which itself is worth a visit, if only to ride the huge Ferris Wheel and sample some of the locally made saltwater taffy.

Another well-known Chicago site is the public sculpture Cloud Gate, located in Millennium Park. Affectionately dubbed “The Bean” by locals, the stainless steel form was sculpted by Anish Kapoor and is usually swarming with tourists. No Chicago trip is complete without a picture of yourself in The Bean’s warped reflection. Millennium Park has several fantastic art installations in addition to The Bean and, on a sunny day, is definitely worth a stroll.

Right next to Millennium Park is the Art Institute of Chicago, a world-class art museum complete with Van Goghs, Monets, Picassos, Pollacks, and the famous Georges Seurat pointillism masterpiece immortalized forever in Ferris Bueller’s Day Off.

On top of all the amazing restaurants, bars, and sights to see, Chicago is also populated by Midwesterners, who are polite and friendly to a fault. Chicagoans really want you to love their city. Especially when the weather is nice, it’s hard to have a bad time in Chicago. Even when it’s cold outside, visitors from all over the globe still fall in love with the Windy City every day.

Places to Visit in Chicago

27 N Wacker Dr, #126
Chicago, IL 60606
instagram: chicagopizzatours
facebook: chicagopizzatour
twitter: chipizzatour

100 W Ontario St
Chicago, IL 60654
instagram: portilloshotdogs
facebook: portillos.hotdog
twitter: portilloshotdog

449 N Clark St
Chicago, IL 60654
instagram: xocochicago
facebook: xocochicago
twitter: xocochicago

430 N Michigan Ave
Chicago, IL 60611
instagram: cheezborger
facebook: billygoattavern
twitter: cheezborger

1616 N Wells St
Chicago, IL 60614
instagram: thesecondcity
facebook: thesecondcity
twitter: thesecondcity

1520 N Damen Ave
Chicago, IL 60622
instagram: violethourchicago
facebook: theviolethour1
twitter: violethourchi

Article originally appeared in Issue 6.1 “Sight and Sound” (Print Issue is Sold Out)