Top things to do in Chicago

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With steel skyscrapers, top chefs, and rocking festivals, Chicago will blow your mind with its low-key, cultured grandeur.

It’s hard to know what to gawk at first. Soaring architecture is everywhere and quirky public art adorns the streets. You might go along and bang, there is an abstract Picasso statue that is not only cool to look at, but you can also go upstairs and climb on it. When you need a break from exploring the city, loosen your belt – there’s plenty to eat here.

Here are the top things to do on your trip to Chicago.

The Art Institute of Chicago is one of the best art museums in the country © AnjelikaGr / Shutterstock

Art Institute of Chicago

The second largest art museum in the country, the Art Institute of Chicago, houses a treasure trove from around the world. The collection of Impressionist and Post-Impressionist paintings ranks second after those in France, and the number of Surrealist works is enormous. Stroll the endless marble and glass corridors and rooms full of Japanese prints, Greek urns, armor, Grant Woods American Gothic, Edward Hoppers Night hawk and a very large, spotted Seurat. The Modern Wing shines with Picassos and Mirós.

Cloud Gate (better known as "the bean") in Millennium Park, Chicago
Cloud Gate (better known as “the Bean”) is located in Millennium Park in Chicago © Dan Welldon / Lonely Planet

Millennium Park

Millennium Park, the playful heart of Chicago, shines with bizarre art in public spaces. Go on, go under Anish Kapoors Cloud gate – aka “the bean” – and touch their silvery smoothness. In summer, let the human gargoyles of Jaume Plensa’s crown fountain douse you with water to cool off. Unfold a blanket of Frank Gehry’s swinging silver ribbon clam as the sun goes down, wine corks pop and beautiful music fills the twilight air. Or try to find the secret garden with prairie flowers and a small gurgling river.

Chicago's First Lady, a cruise ship on the Chicago River, heads for Lake Michigan on a 75-minute architectural tour
Take a river tour to see Chicago’s stunning architecture from a new angle © jessicakirsh / Shutterstock

Architecture cruises

Who cares if all those neck curves hurt a little backwards? There’s no better way to feel Chicago’s steel power than to look up from the water as cloud towers slide by and iron bridges open to show the way. The skyline takes on a surreal majesty as you soar through its shadows on a river tour, and landmarks flash by flashy landmarks. The guides’ architecture lesson continues so that by the end of the day you will know your Beaux Art in an international style.

What is a Chicago Style Hot Dog?

Eats globally

In recent years, chefs like Grant Achatz, Rick Bayless, Stephanie Izard, and many others have put Chicago on the culinary map. They won tons of James Beard Awards, and suddenly international critics were calling Chicago one of the best restaurants in the world. The nice thing here is that even the liveliest restaurants are accessible: they are visionary yet traditional, essentially pubby and reasonably priced. You can also enjoy a great variety of global food in Chicago’s Puerto Rican neighborhoods jibaritos (Steak covered with garlic mayo and served between thick, crispy fried plantain slices that form the “bread”) to Indian samosas and Polish pierogies.

Exterior view of Wrigley Field, Chicago
Sports tradition has a long tradition at Wrigley Field in Chicago © FiledIMAGE / Shutterstock

Wrigley field

A tangible sense of history comes to life at Wrigley Field, a 100-year-old baseball park, thanks to the hand-rolled scoreboard, iconic neon entrance sign, legendary curses and time-honored traditions that are played here. Shoveling hot dogs down and drinking beer in the noisy grandstands make for an unforgettable afternoon. The area around the stadium is like a big street party on match days: young people celebrate in bars outside, children lick ice cream cones and die-hard fans sit on stools in ancient pubs with sticky floors.

View of the cityscape of Chicago with the Willis Tower in the middle
The Willis Tower is Chicago’s tallest skyscraper © Songquan Deng / Shutterstock

Sky high view

For lovers of superlatives, the Willis Tower is just the thing: the tallest building in the city (and one of the tallest in the world). Take a deep breath during the deafening 70-second ride on the elevator to the Skydeck on the 103rd floor, then walk to one of the glass ledges that jut out into the air. Look down about 1400 feet. Crikey. The 875 N Michigan Ave building on the lake (formerly known as the Hancock Center) also towers high in the sky. Ascend to the Signature Lounge on the 96th floor, order a cocktail and watch the city sparkle around you. It’s especially beautiful at night.

A drummer on stage at Buddy Guy's Legends Jazz Club in Chicago, Illinois
A drummer on stage at Buddy Guy’s Legends Jazzclub © Marc Lachapelle / 500px

Blues and rock

In Chicago, no genre is as iconic as the blues – the electric blues, to be precise. When Muddy Waters and friends plugged in their amplifiers in the 1950s, guitar grooves hit new decibel levels. Hear it in clubs across town like Buddy Guy’s Legends, where the icon herself still takes the stage, or Rosa’s Lounge, where it’s a bit shabby and dirty. The blues paved the way for rock’n’roll, so it’s no surprise that cool little clubs with edgy indie bands frolic on many street corners.

Comedy and theater

Half a century ago a group of pranksters began deliberately performing unstructured skits in a Chicago bar, and voilà – improvisational comedy was born. Second City still feeds the best in the business, though several other improvisational theaters are also working with alcohol-fueled proposals that cheer the audience on. Among the city’s 200 theaters are mighty actors like the Hollywood star-laden Steppenwolf and loads of provocative “off-loop” companies like the Neo-Futurist Theater (which bases its entrance fee on a die roll).

Public works of art "Monument with a standing beast" by Jean Dubuffet in Chicago
Jean Dubuffer’s sculpture entitled “Monument with Standing Beast” is popularly known as Snoopy in a Blender © Maremagnum / Getty Images

Public art

You can’t walk two blocks downtown without encountering an extraordinary sculpture. The grandfather is Picasso’s untitled sculpture (what the hell is that – an Afghan greyhound?) Set right in Daley Plaza. The abstract creation by Jean Dubuffet officially bears the title Monument with a standing beast, but everyone calls it “Snoopy in a Blender”. Marc Chagall’s large mosaic Four Seasons is more recognizable and shows scenes from Chicago. Alexander Calder’s massive, red-pink flamingo could pass for its namesake, but only after you’ve had a few beers.

View of Navy Pier with the Chicago skyline in the background
Chicago’s Navy Pier is one of the city’s most popular tourist attractions © f11photo / Shutterstock

Navy Pier

Far away from the skyline and into the blue of Lake Michigan, the 800 meter long Navy Pier, one of Chicago’s most visited attractions, stretches out. Its charm revolves around the cool breezes and sweet views, especially from the stomach-spinning, 60-foot-tall Ferris wheel. The little ones are enthusiastic about high-tech rides, spray fountains, large boats and greasy snacks. Live music, Shakespeare theater, and lush fireworks keep everyone else entertained. A smart renovation has added public spaces, performance rooms, art installations and a free cultural program.



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