Explore Chicago: what to see, where to stay and things to do
Often overshadowed by and likened to its East Coast counterpart, New York City, Chicago beats to the beat of its own drum. Razed to the ground by a fire in 1871, the city has spent the last 150 years or so becoming a patchwork of architectural styles and influences. But draw your eyes down from the towering skyscrapers and there's award-winning dining, entertainment galore and a city that's easy to fall in love with.
Must-visit Chicago neighbourhoods
With 77 distinct districts and neighbourhoods making up the city, knowing where to go and when can be overwhelming. We've narrowed down our favourite areas of Chicago that you can easily fit into an extended weekend break.
The Loop & Millennium Park
The very heart of the city, Chicago's downtown is called the Loop thanks to the elevated L train looping around it, marking the borders of the neighbourhood. Home to most of the city's iconic attractions, this is where you can find emblematic buildings, board a must-do river cruise and take in Millennium Park – home to the famous Bean, or Cloud Gate. It's here that you can catch that big city buzz, walk down State Street or catch an award-winning show in the celebrated Theatre District.
Don't miss the Chicago Architecture Center, then head down the Chicago Riverwalk and return at night to see free public art projections Art on theMART.
Logan Havens/Alamy Stock Photo
Fulton Market & West Loop
The city's most recent regeneration project, Fulton Market has quickly become its trendiest spot. As tech startups have gradually left California in favour of Chicago – part of the Silicon Prairie – offices, cool restaurants, boutique stores and bars have taken over this once-industrial area. A new wave of trendy hotels have found their home here too, and it's also within easy access of the Loop.
The adjacent West Loop is the city's best dining destination – book a table pretty much anywhere on Randolph Street, or 'Restaurant Row' and you're pretty much guaranteed a delicious dinner. There's everything from high-end restaurants with tasting menus to juicy burger joints and buzzy cocktail bars.
Magnificent Mile & River North
Decidedly fashionable, Magnificent Mile is Chicago's best shopping destination with everything from designer stores to concept boutiques and much-loved, mass-market brands. Home to yet more stunning architecture, it's worth coming here for various must-do Chicago experiences, like enjoying afternoon tea at The Drake Hotel's historic Palm Court or heading up 875 North Michigan Avenue (formerly the John Hancock Center) to dangle above the city streets at 360 CHICAGO.
chicagoview/Alamy Stock Photo
Hyde Park
Leave the skyscrapers behind and see a different side to the city in Hyde Park. Home to the University of Chicago, its ivy-draped Gothic-inspired buildings and suburban townhouses feel a million miles away from the glass and steel jungle of the Loop. It's well worth coming here for a stroll after taking in the sublime Museum of Science and Industry. Give it a few years and the brand-new Obama Presidential Center will draw in even more visitors to the area.
For yet more exceptional architecture, visit Frank Lloyd Wright's Robie House. The 1910 suburban family home, an excellent introduction to Wright's emblematic organic architecture, will surprise with its contemporary features that were unusual for the time, like open-plan living areas and built-in furniture. If you're keen to learn more about the famous architect's work, head out of town to Oak Park where you'll find his home and studio.
Tip: Choose Chicago runs free Chicago Greeter tours, where passionate locals will guide you around a neighbourhood of your choice, talking through its history, landmarks and off-the-beaten-path attractions. Request a free tour here.
Top things to do in Chicago
Get your bearings with a river cruise
Arguably the best way to see Chicago, taking a river cruise is an absolute must. Make sure to book the Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady – led by extremely knowledgeable docents, these 1.5-hour cruises do a fantastic job of introducing the city's key buildings, as well as its history and architecture, in a digestible, understandable way.
Depending on the weather, make sure you're dressed warm enough to sit on the open-air top deck for the best views. In colder months there are hot drinks available onboard as well.
Sean Pavone/Alamy Stock Photo
Feel the music at a blues club
Chicago is excellent when it comes to entertainment, and you could spend every night here enjoying some of the best theatre, music and comedy. Founded in 1968, Kingston Mines is the oldest continuously operating blues club in Chicago. Bob Dylan, Mick Jagger and David Bowie have all graced the rustic venue's two stages. Today, there's live music every night – order a classic barbecue meal and a beer, then kick back and let the music flow through you. The musicians' skill and love for the blues is quite something to experience, so it won't be long before you catch yourself tapping your feet to the rhythm of the beat.
See the city from above
High above the streets of the Loop, all the way up on the 103rd floor of the Willis Tower (better known to most by its old moniker, Sears Tower), Skydeck Chicago is a thrilling experience. Your visit starts with an interactive and engaging exhibit about Chicago and its history, from the Great Fire to its most famous residents and world-famous foods, until a nearly minute-long trip in a lift takes you up to what feels like the sky.
After you've taken in the magnificent views, make sure you experience The Ledge – these glass boxes will make you feel like you're floating above the city and ensure you have some striking photos to remember your visit. It will get your pulse racing, that's for sure, but it's worth it.
EmmePi Images/Alamy Stock Photo
Catch a comedy show
Another aspect of Chicago's vibrant entertainment life, improvisational comedy is huge. Operating since 1959, The Second City is a historic venue that's acted as a launching pad for some of the country's best-loved comedians. Famous alumni include Tina Fey, Steve Carell, Stephen Colbert, Amy Poehler and Jordan Peele, and it's often regarded as one of the principal comedy troupes in the country.
Visit the Art Institute of Chicago
Undoubtedly one of the country's – and the world's – best art museums, the Art Institute of Chicago is chock-full of some of the world's best art. You could easily spend hours here, but it's possible to see its greatest treasures within an hour – don't miss Grant Wood's American Gothic, Van Gogh's Self-Portrait and The Great Wave off Kanagawa by Hokusai, as well as a selection of works from Georgia O’Keeffe, David Hockney and Claude Monet, including his Water Lilies.
Afterwards, cross the road to Millennium Park and stop by the iconic Bean for some classic Chicago photos.
PhotoSpirit/Alamy Stock Photo
Where to stay in Chicago
Check into the stunning LaSalle Chicago, an Autograph Collection hotel, for a flavour of Art Deco life. One of the city's newest luxury hotels, its design incorporates plenty of original detail and its downtown location is perfect for easy access to the city's key destinations. Rooms and suites come with sophisticated interiors, marble-clad bathrooms and comfortable queen and king-sized beds. Guests have access to a 21st-floor fitness centre offering gorgeous views and there's also a spa and the brilliant Grill on 21, offering all-day dining and drinks.
If you'd rather stay in Chicago's most happening neighbourhood, book a room in Fulton Market's The Hoxton. The hotel's 192 rooms range from 'Snug' to 'Roomy' and there's a co-working space for those taking work on the road. Perfect for creative types, it's within easy access of concept stores, innovative dining and funky bars.
For an art-filled escape in the heart of Chicago's top shopping destination, book 21c Museum Hotel in the Magnificent Mile neighbourhood and enjoy a restful night's sleep surrounded by art before fuelling up at the hotel's Lure Fishbar – the breakfast menu features pancakes, French toast, multiple egg dishes and a lobster frittata.
What to eat in Chicago
There are a great many things this city is passionate about, including architecture and sport – and fortunately for visitors, food is most certainly one of them. Whether it's simple, on-the-go lunches, innovative takes on much-loved classics, award-winning high-end dining or historic dishes known the world over, Chicago has it all in spades.
Deep-dish pizza and the Italian beef sandwich are two absolutely unmissable Chicago classics so you'll see many (unsuccessful) imitations all over town. You want to make sure you get the real deal, though. Al's Italian Beef has been serving subs packed full of thin slices of seasoned roast beef since 1938. Brought to the Chicago stockyards by Italian immigrants, the exact origin of this famous sandwich is unknown, however, Al's is known as the place to try it. Similarly, Lou Malnati's and Giordano's go head-to-head when it comes to the best deep-dish pizza in town. Which one's better? You'll just have to find out for yourself...
For other all-American classics like biscuits and pies, presented in new and imaginative forms, head out to Bang Bang Pie & Biscuits. A simple, low-key neighbourhood joint, its biscuits are wonderful and pies incredible. Go for the ham biscuits or chicken pot pie; and classic apple pie for dessert. The pie menu changes regularly (and with the seasons) so look out for the specials board. When in Hyde Park, stop by President Obama's favourite Valois Restaurant for diner classics.
Classics aside, Longman & Eagle in Logan Square has a particularly contemporary European feel with small plates, rustic tables and gentle candlelight. For a meal that will excite and challenge the taste buds, share grapes and burrata, chicken Milanese and sweetbread stroganoff. Equally, Wrigleyville's Swift & Sons Tavern offers top-notch dining in a casual, relaxed setting with views of Wrigley Field – the second-oldest Major League Baseball field and home to the Chicago Cubs. You won't go wrong by ordering half a dozen raw oysters to share and steak frites with pepper sauce.
For international flavours, check out Avlí with its modern Greek dishes (get the roasted aubergine with pitta and the pork shoulder gyros sandwich) and Alla Vita for elevated Italian pasta, pizza and crispy-as-you-like chicken parmigiana.
Map of Chicago
Find all of our favourite places in Chicago using our handy map:
For more information, go to Choose Chicago.
Lead image: Susan E. Degginger/Alamy Stock Photo
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