Frank Sinatra sang “Bet your bottom dollar you lose the blues in Chicago, Chicago” – seems like a pretty solid recommendation. But don’t take Ol’ Blue Eyes word for it, after all, he also sang “In Chicago, Chicago my home town” and we all know he was a Jersey boy—so go check it out for yourself! Here are my recommendations on what to do in Chicago for cultural travellers in search of great art, architecture, history, food and fun.
Disclosure: I may earn compensation from the purchase of any product or service linked on this website, at no extra cost to you. I only link to products I use and love, therefore feel comfortable recommending.
Visit the Chicago Institute of Art
Founded in 1879 as a museum and school for the fine arts, The Chicago Institute of Art 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 has be extended over the years to accommodate the museum’s expanding collection which include: 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.
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 the Chicago Cultural Center and its 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 and 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 being the largest stained-glass Tiffany dome in the world at 11.5m (38ft) in diameter and consisting 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.
Field Museum of Natural History and Shedd Aquarium
Continue walking south through Grant Park and you eventually end up in an area called Museum Campus which is a 57-acre park that 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 the museums, I recommend going down to 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!
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 by reclaiming derelict and unused spaces as a “living urban canvas”. Here you’ll find many large-scale murals by local and international street artists like Brazilian Kobra’s vibrant Muddy Waters portrait and Chicagoan Jacob Watts’ surreal image of a moose blowing pink bubblegum.
Get your kicks on Route 66
Also a stone’s throw from the Institute of Art is a sign demarking the start of old Route 66. It’s highly unlikely you’ve never heard of the Route 66, it inspired a famous song recorded by everyone from Nat King Cole to John Mayer. The “Mother Road” as it’s often referred, was one of the original roads in the US Highway System running from Chicago, Illinois to Santa Monica, California. The road became the favoured path for those migrating west, particularly in the 1930s and saw many communities spring up along its path. It was eventually superseded in 1985 by newer roads of the Interstate Highway System which saw many of these small towns fade. However, sections of the Route are nostalgically designated Scenic Byways called “Historic Route 66”.
Seek glitz in the Theatre 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, Oriental, Goodman and Auditorium Theatres.
Chill out with an architecture river cruise
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 up and down the Chicago River. Along the way, a guide will interpret the city’s outstanding architecture and fascinating history including why the River runs backwards (away from Lake Michigan).
Cruise 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 it’s not my cup of tea, but there are other reasons to see this part of the city. These include the amazing terracotta Wrigley Building, historic Chicago Water Tower, neo-Gothic Tribune Tower and 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.
Explore Frank Lloyd Wright’s home and Ernest Hemingway’s birthplace
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, take walk around the historic neighbourhood with an audio tour guide. 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.
Dine and drink
Chicago is not short on good eats. Of course, you are expected to partake in at least one deep-dish pizza (which was a lacklustre experience IMHO), and Chicago-style hot dog (ick!) but there is plenty of better fare to clean your palette with afterwards. Chicago has 22 Michelin-starred restaurants as of this post being written and many, more affordable establishments. Cupitol serves up a good, healthy, casual breakfast on the go (avocado wrap please), though unfortunately, their latte tasted like a cup of hot milk. Goddess and the Baker are another healthy breakfast option with much better coffee, located in The Loop.
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.
Plan a trip to Chicago, Illinois
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,