Hold on to your hat in the Windy City!
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 till you drop in the town where Mr Selfridge declared that the customer is always right, food is honoured with Michelin stars and thumbs pointing decidedly up, and the roots of jazz and blues go deep.
Enjoy this Chicago travel guide.
Five Chicago tours and experiences we love
The Chicago CityPASS is one of the best deals for visitors to the Windy City. It provides discounts on admission to five premier attractions, including Skydeck Chicago, the Field Museum of Natural History and Shedd Aquarium.
This Chicago hop on hop off bus tour will let you explore the city at your own pace. See all the key sights, including Lincoln Park Zoo, Wrigley Field, Willis Tower, The Chicago Theatre, Chicago History Museum, and many more. Embark and disembark as often as you like at designated stops.
Need to get your bearings in Chicago? This half-day tour is the perfect introduction to the city. Discover the highlights of North Side and South Side and enjoy a drive along the Outer Drive. You’ll see Washington Grant Parks, and make a stop at the fascinating Lincoln Park Conservatory.
Discovering Chicago’s architecture is one of the great joys of travelling to this amazing city. During this fabulous two-hour stroll you’ll experience opulent exteriors and interiors from the Art Deco period, along with the classic finishes associated with Art Moderne.
Descend to the shadowy world of the Prohibition-era speakeasy on an adults-only tour of four historic Chicago bars. Learn why the sale of alcohol was banned for more than a decade in the US, and about illicit establishments where liquor, jazz and mobsters ruled the roost.
Chicago for history lovers
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 buildings: the landmark Chicago Water Tower — a rare Great Fire survivor; spectacular Art Deco structures such as the Chicago Board of Trade Building (check out the lobby!); and Modernist marvels including the Willis Tower with its observation deck (and very freaky glass balcony known as The Ledge) on level 103.
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.
Top cultural experiences 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.
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 such as Al Capone favourite The Green Mill are true Americana.
Great places to eat in Chicago
The world’s biggest food festival is another of Chicago’s many claims to fame.
Taste of Chicago delivers the city’s yummiest new and classic cuisine — everything from donuts to fine dining. For the latter at any time of year, book ahead for three-Michelin-starred experiences at Alinea or Grace.
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).
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.
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, including Vintage Underground and Stitch for contemporary accessories.
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.
Fancy watching these pyrotechnics from above? At the nearby John Hancock Center’s 96th floor Signature Lounge, a cocktail is cheaper than observation deck entry, and you’ll get views across most of the city.
Do you have any tips to add to our Chicago travel guide? We would love to hear from you. Please send us a message.
Additional images: Bigstock
About the writer
Patricia Maunder has been a media professional for more than 20 years, and has worked in print, online and radio. 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 travelled in every continent except the one that’s beckoned since she was a child — Antarctica. A travel writer as well as an arts journalist, she enjoys culturally themed journeys and nature-based adventures.