Frank Sinatra sang “Bet your bottom dollar you lose the blues in Chicago, Chicago” – seems like a pretty solid recommendation, so go check it out for yourself! After several visits to the Windy City, here are my recommendations on what to do in Chicago for cultural travellers in search of great art, architecture, history, food and fun.
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Top things to do in Chicago
Visit the Chicago Institute of Art
The Chicago Institute of Art was founded in 1879 as a museum and school for the fine arts. It moved into its current home in 1893 as the city wound down from hosting the World’s Columbian Exposition. The beautiful Beaux-Arts building framed by a pair of bronze lions was extended over the years to accommodate the museum’s expanding collection.
Here you’ll find: Seurat’s scandalous A Sunday on La Grande Jatte, Hopper’s Nighthawks, Van Gogh’s The Bedroom, Wood’s American Gothic, Chagall’s American Windows, and Motley’s Nightlife. See some of my favourites from the Institute here.
Cruise the architecture
There’s no better way to see Chicago on a warm, sunny day than to sit back on the rooftop of a boat and cruise the Chicago River. Along the way, a guide will interpret the city’s outstanding architecture and fascinating history. You’ll also learn the story of why the River runs backwards (away from Lake Michigan).
Tip: If the weather isn’t cooperating, visit the Chicago Architecture Center for indoor insights into the city, it’s history and urban landscape. You’ll find exhibits on the Windy City’s architectural gems, past, present and planned.
Shop the Magnificent Mile
Chicago’s premier commercial district is located on a section of Michigan Avenue north of the Chicago River. I can’t report on the shopping as rampant consumerism is not my cup of tea. However, there are other reasons to see this part of the city. These include the amazing terracotta Wrigley Building, historic Chicago Water Tower and neo-Gothic Tribune Tower.
This is also where you’ll find the 94-floor views over Chicago and Lake Michigan from the 360Chicago in the John Hancock Center. I’m not going to lie. On a busy day you’ll spend more time in the queue to go up and down the elevators, than you’ll spend in the observatory itself. But the views are worthwhile!
Tour Frank Lloyd Wright’s home and studio
Take a tour of renowned architect Frank Lloyd Wright’s self-designed home and studio in the outer suburb of Oak Park. You can drive, Uber or take a train from downtown to the upscale neighbourhood that contains a number of Wright-designed homes. After taking a tour of the starchitects home and studio, walk around the historic neighbourhood with an audio guide.
Tip: A few blocks away from Frank Lloyd Wrights home, you will also find the birthplace of Ernest Hemingway that has been transformed into a living museum.
Field Museum of Natural History and Shedd Aquarium
Continue walking south through Grant Park. Eventually you’ll end up in an area called Museum Campus. This 57-acre park encompasses the Adler Planetarium, Shedd Aquarium, the Field Museum of Natural History, Soldier Field and McCormick Place.
Even if you don’t have time to go inside, I recommend visiting the park just to see the architecture. You can drop into the foyer of the Field Museum and Shedd Aquarium to get an idea of their impressive interiors. The ocean-themed details of the Shedd Aquarium are outstanding!
Explore the Lakefront Trail
When the weather is good, take to the Lakefront Trail on foot or rented bike. Take in the green-blue of Lake Michigan, as you travel northward along the Gold Coast, passed Lincoln Park, as far as Montrose Point Bird Sanctuary or Kathy Osterman Beach. Pack a picnic, wear sunscreen and make plenty of stops to enjoy the views back at the Chicago skyline.
Dine on Chicago favourites
Chicago is not short on good eats. Of course, you are expected to partake in at least one deep-dish pizza and a Chicago-style hot dog. When in Rome, right?! There is also plenty of better fare available.
Chicago has 21 Michelin-starred restaurants as of August 2024 and many, more affordable establishments. Goddess and the Baker are a local chain with healthy breakfast options and decent coffee. Among our foodie favourites were Jimmy Bannos Jr’s homage to pork The Purple Pig and Rick Bayliss’ Frontera Grill.
Free things to do in Chicago
Stroll Millenium and Grant Parks
The Chicago Institute of Art is situated between Millenium Park and Grant Park. If the weather is right, take a stroll through both green spaces to see landmark public art and architecture on the banks of lovely Lake Michigan. You will find a timeline of pieces ranging from the contemporary, metallic bubble of Cloud Gate completed in 2006, to the landmark, Rococo-inspired Buckingham Fountain dedicated in 1927. My personal favourite is the Jay Pritzker Pavilion designed by the incomparable Frank Gehry.
See Chicago Cultural Center’s magnificent Tiffany Dome
The Chicago Cultural Center was originally built to house the central library and Grand Army of the Republic (GAR) meeting hall and memorial. It was later transformed into a Cultural Center. Designed in Beaux Arts style, the opulent building opened in 1897. The Cultural Center has two beautiful domes, one over the GAR Memorial and another over Preston Bradley Hall.
The Preston Bradley Hall cupola is well known for the largest stained-glass Tiffany dome in the world. The impressive leadlight installation measures 11.5-m (38-ft) in diameter and consists of around 30,000 pieces of glass. Make sure you take in both the Washington and Randal Street ends of the building, as each has something to offer. If you can, take a free building tour offered Wednesdays through Saturdays at 1:15pm – details here.
Scope out some sculpture
Chicago’s art scene isn’t all inside institution walls. You can see it for free just wandering the streets. From Picasso to Miró, Chagall to Calder, you can find works contributed by world-renowned artists. These also include more contemporary works like Anish Kapoor’s Cloudgate (colloquially known as The Bean), and Jaume Plensa’s Crown Fountain. Learn more about the city’s public art collection on the official City website.
Hunt for murals in the Wabash Arts Corridor
While we are on the subject of art, walk south of the Institute from Van Buren St to Roosevelt Road. Between State Street and Michigan Avenue, and you’ll find yourself in the Wabash Arts Corridor. The urban art project by Columbia College Chicago has been transforming the South Loop business district since 2013. The program aims to reclaim derelict and unused spaces as a “living urban canvas”. Here you’ll find many large-scale murals by local and international street artists – from Kobra’s colourful portrait of Muddy Waters to Watts’ surreal image of a moose blowing pink bubblegum. You’ll find some fun and fantastic murals along the Corridor!
Get your kicks on Route 66
Also a stone’s throw from the Institute of Art is a sign demarking the start of old Historic Route 66. It’s highly unlikely you’ve never heard of U.S. Highway 66. It inspired an uber famous song recorded by everyone from Nat King Cole to John Mayer, and featured in the Disney movie Cars. The “Mother Road” as it’s also referred to, was one of the original roads in the US Highway System, running from Chicago, Illinois to Santa Monica, California.
Drop by the Peacock Doors
If you’re a door lover, you can’t go passed the Tiffany & Co. bronze peacock doors at Palmer House. Located in The Loop, the hotel now operated by Hilton features lavish doors installed in 1873. The doors were designed for The House of Peacock store that was then located on the hotel’s first floor–hence the opulent peacock motif. According to the plaque each door weighs more than a half-ton and together they are valued at over a million dollars.
Wander into The Rookery
Located in The Loop, the Rookery Building is a Chicago Landmark and is listed on the National Register of HIstoric Places. The architectural treasure was designed by Burnham and Root and completed in 1888. In 1905, Frank Lloyd Wright redesigned the building’s atrium into a light-filled lobby. The atrium is open to the public Monday-Saturday and is worth a wander through. There are also tours held Monday-Friday. Check the building’s visiting details here.
Things to do in Chicago at night
Sunset cocktails
As day turns to night, find yourself a rooftop bar to sip something special while you take in the urban design of Chicago from above. London House rooftop is the perfect place to start, right on the river with wonderful views of the Wrigley Building and the Chicago Tribune Tower.
Go to a show
Chicago has an amazing theater scene that rivals New York’s Broadway district! Even if you don’t have the time or inclination to see a show, it’s worth taking a wander around the downtown Theatre District, located in The Loop. There are countless impressive architectural moments and shimmering marquees to discover such as the Chicago, Nederlander, Goodman and Auditorium Theatres.
Seek out a speakeasy
After dinner, check out the speakeasy-style bars such as tiki-inspired Three Dots and a Dash, and Watershed’s parlour style setting with craft beers, artisan spirits and wines all sourced from around the Great Lakes region.
Listen to some jazz
Jazz was born in New Orleans and quickly migrated northward to Chicago in 1915. It stowing away in the minds and suitcases of workers from the South who travelled to the Second City seeking job opportunities. If you’re looking for nightlife with an authentic Chicago vibe, its only fitting to visit one of the city’s iconic jazz clubs. Enjoy a show at Andy’s Jazz Club, Green Mill Cocktail Lounge or Constellation.
Improvise for some comedy
Chicago’s The Second City is THE place to see improvisational theatre and sketch comedy. In fact it trains comedians, with its own training center and film school. Since its establishment in 1959, the revolving cast of comedians performing with the Chicago troupe have included none other than Alan Alda, John Candy, Bill Murray, Eugene Levy, Steve Carell, Tina Fey, Amy Poehler, Mike Meyers and Catherine O’Hara. The theatre is located in Chicago’s historic Old Town neighbourhood and is an easy bus ride from downtown.
Tip: For a budget-friendly show, there is a regular Ten Dollar Comedy Showcase by The Second City at the Blackout Cabaret.
Cultural travellers, I hope you find your Windy City bliss with this guide on what to do in Chicago. Let me know in the comments below.
Peace, love & inspiring travel,
Madam ZoZo
