Only got a couple of days to get to know a new city? Our Big Five City Guides can help. We break each destination down into culture, history, dining, shopping and relaxation must-sees and dos.
Sure, it can get breezy, especially when winter gales blast off Lake Michigan (so think twice about Chicago in January and February!). What I really mean is there’s so much happening in America’s third-largest city that it will sweep you off your feet.
A financial, commercial and cultural hub for two centuries, Chicago has long impressed visitors. In the skyscraper’s birthplace, architecture stuns (and not merely for its height), while from park to pier, open spaces invite you to unwind and rejuvenate. You can shop ’til you drop in the town where Mr Selfridge declared that the customer is always right, style up or down for dinner (it will be memorable either way), and enjoy a rich jazz and blues heritage.
Chicago city guide: Magnificent Mile. Image: Bigstock
Get the most out of your stay with a Chicago City Pass, which gives you access to popular Shedd Aquarium, Skydeck Chicago (on the 103rd floor of the former Sears Tower), Field Museum (one of the largest natural history museums in the world), and your choice of three other top attractions.
This Chicago city guide is packed with ideas for things to see and do. Enjoy your visit.
Top Oz Tours offers a great range of USA day tours, guided experiences, and attraction tickets and passes. There are no booking or credit card fees when you book through us, and you’ll have access to the widest choice of activities and most competitive prices.
Extraordinary engineering is at the heart of Chicago’s urban success.
In the second half of the 19th century, the city centre — buildings, sidewalks and all — was raised a metre or more to allow better drainage, the world’s first skyscrapers went up after the Great Fire of 1871, and the Chicago River’s flow was permanently reversed!
Discover the city’s past through its landmark buildings, including the Chicago Water Tower (a rare Great Fire survivor), the Art Deco Chicago Board of Trade Building (check out the lobby!), and modernist marvels like the aforementioned Willis Tower (formerly the Sears Tower) — with its observation deck and very freaky glass balcony known as The Ledge.
The renowned Chicago Architecture Foundation makes history and design come alive on dozens of themed tours. The most popular — of any tour in Chicago — is the introductory river cruise. Try booking a summer evening cruise: remarkable buildings slide past in late afternoon sunshine and evening twilight, before the whole gleaming city is seen at night from the lake.
Image: Chicago Architecture Foundation
The Prohibition era (1920 to 1933) saw gangsters like Al Capone and Bugs Moran rise to infamy in Chicago. Learn more on a guided tour of buildings and landmarks related to mob rule.
Top cultural activities in Chicago
Chicago has a diverse and dynamic cultural scene.
The Art Institute of Chicago’s store is a chic shopping option, but don’t get waylaid and spend all your time there. The merchandise is inspired by a vast collection noted for American, Impressionist and Post-Impressionist art. Make like Ferris Bueller and see Seurat’s mesmerising painting — A Sunday Afternoon on La Grande Jatte.
Chicago city guide: Cloud Gate
Downtown is rich with public artworks, including Picasso’s untitled sculpture (Chicagoans still argue about what it represents). Anish Kapoor’s Cloud Gate, a seamless, highly reflective wonder, popularly known as The Bean, became an instant icon in 2006.
Chicago’s Lyric Opera is among the world’s leading opera companies, and jazz and blues grew up here. The annual Chicago Blues Festival is the biggest music event in town — even bigger than the alt-rock Lollapalooza — and resident bluesman Buddy Guy still plays at his eponymous club. Jazz dens like Green Mill (an Al Capone favourite) and Andy’s Jazz Club are true Americana.
Chicago city guide. Image: Lyric Opera
Great places to eat in Chicago
The world’s biggest food festival is another of Chicago’s many claims to fame.
Taste of Chicago in July delivers the city’s yummiest new and classic cuisine — everything from donuts to fine dining. To experience the latter at any time of the year, book a table at Michelin-starred Alinea.
Chicago’s greatest gastronomic treasure though is deep-dish pizza — a thick, molten mess that’s totally delicious and tummy-filling (seriously, order the small!). It’s everywhere, but consider the original Pizzeria Uno where deep-dish was born.
There’s also the Chicago-style hot dog, which is said to be ‘dragged through the garden’ because of its myriad garnishes — though never ketchup (some vendors won’t even supply it).
Feast on a Chicago hotdog. Image: Bigstock
Rounding out Chi-Town’s fast-food trinity are Italian beef sandwiches. Mr Beef does them best.
Where to shop in Chicago
There’s plenty to keep shopaholics on the go in Chicago.
The Architecture Foundation’s store is another top option for stylish souvenirs, while the Marshall Field’s Building on State Street is a great place to combine memorable shopping, design, history and even dining. The man behind London’s Selfridges started out at this pioneering department store, where ornate clocks, Tiffany ceiling mosaics and the 1907 dining room still impress at what is now Macy’s.
North Michigan Avenue — the Magnificent Mile — is Chicago’s premier shopping destination. American idols including Bloomingdale’s and Saks Fifth Avenue tempt here, as well as international luxury labels such as Burberry and Chanel.
Chicago city guide: Shop along the Magnificent Mile.
This strip also offers gems like luxe chocolate shop Vosges, or head just north of downtown to the eclectic stores of the Wicker Park-Bucktown neighbourhood. Vintage Underground is a must-visit.
Ways to relax in Chicago
Locals and visitors alike love Millennium Park, which was built over rail yards and parking space.
Effectively the world’s largest rooftop garden, the park hosts free concerts at the dynamic Frank Gehry-designed bandshell, and engaging public art — including The Bean and interactive Crown Fountain.
From basketball’s Bulls to ice hockey’s Blackhawks, sport is legendary in Chicago. A quintessential American experience is a baseball match at Wrigley Field — home of the Cubs, who broke a 108-year World Series drought in 2016.
Stadium crowds are nothing though compared to what you’ll encounter at Navy Pier. This 100-year-old, kilometre-long structure is the city’s top tourist attraction and the departure point for Lake Michigan pleasure cruises. The pier boasts everything from a Ferris wheel and children’s museum to winter ice-skating and summer fireworks.
Chicago city guide: Navy Pier
Fancy watching those pyrotechnics from above? Head up to The Signature Lounge on level 96 of the John Hancock Center and sip a cocktail against the backdrop of glittering city lights.
Browse our range of Chicago tours and experiences here.
Do you have any tips to add to our Chicago city guide? We would love to hear from you. Please leave a comment below.
Additional images: Bigstock
About the writer
Patricia Maunder is a freelance travel writer and arts journalist, and has worked in print, radio, and digital media. Currently based in Melbourne, she considers the Canadian city of Montreal to be her ‘other’ hometown — having lived there from 2012 to 2016. Patricia has visited all but one of the continents, and Antarctica continues to beckon — as it has done since she was a child. She enjoys culturally themed journeys and nature-based adventures.
