Architecture, sports and live music are three defining characteristics of Chicago. Rock through the museums, parks and grand avenues in search of splendid art and opulent structures, or sit back and observe the skyline via a river cruise. Sport fans can eagerly jump between Wrigley Field, United Center and tavern screens for non-stop game watching, whereas musical peers have choice of theatres and insane music festivals. Sounds like a city of fun, right?
Start fresh with Millennium Park
Capturing the modern-day spirit of Chicago is the shining Millennium Park, an award-winning space that symbolizes change. It is one of Chicago’s most popular tourist attractions, climbing up the list with a host of community initiatives, public art and architectural pieces. Discover the world’s largest green roof, Lurie Garden binding perennials, bulbs and grasses in bold design. Or, catch a concert at the 11,000-capacity Jay Pritzker Pavilion, which is frequented by the Chicago Symphony Orchestra and major music headliners. Millennium Park also offers bike rentals at McDonald’s Cycle Center so you can explore the expansive Grant Park that it is located in.
Size up at the Field Museum of Natural History
Having opened in 1893, Field Museum has since collected over 24 million items. If the 37-meter Titanosaur didn’t give it away, this collection is a sweeping look over the natural world, featuring excavated fossils, gemstones and specimens of extinct species. You can loiter around themed halls like anthropological Ancient Americas and Ancient Egypt, or dig deep into the Tibetan and African cultures. If you like things of earthen quality, the Geology Hall totes Chinese jade and stained glass. Field Museum is a definite must-visit.
Drift down the Riverwalk
Walking will gift you certain views you wouldn’t otherwise find, and Chicago sure spoils these on-foot explorers. Cutting through downtown along Chicago River is the 1.25 miles long Riverwalk, leading up to Wolf Point. With a backdrop of stately buildings, terraces, dramatic bridges and urban scenery, it is a must-do for photographers. Keep an eye out for the Wrigley Building (not that you’d miss it) or Ellen Lanyon’s Gateway; there are plenty of architectural highlights and public art in form of installations, graffiti and tiled murals. The Riverwalk is especially evocative at night, cafés and grill bars lighting up the walkway with date-night ambiance.
Get sea deep at Shedd Aquarium
Sharing location with the Field Museum and Adler Planetarium, the Shedd Aquarium may no longer be the world’s largest indoor aquarium, but it is still an impressive collection of aquatic creatures. Caring for some 30,000 sea life, the aquarium stresses on an immersive environment. Amazon Rising recreates the roots of rainforest trees to house anacondas, piranhas and freshwater stingrays; the Wild Reef, four shark species. For friendly mammals, spend some time waving at the sea lions and sea otters at the Oceanarium.
Indulge in the arts at Chicago Theatre
Bring home a snapshot of Chicago Theatre’s iconic marquee and vertical sign even if you’re just passing by. The red and yellow glowing boards have been featured in movies, but look behind it for a beautiful central arch with Tiffany stained glass. The façade was intended opulence during its 1921 establishment. Much like its grand exterior, the performances held here are top-tier. Pick from their extensive programme of performance arts, as varied as dance theatre and comedy acts. Sometimes the venue also hosts talks by famous cultural figures.
A multifaceted field trip around Grant Park
Grant Park in autumn is exceptionally pretty, broad litters of golden leaves sharp against the green shrubbery. An open space that is home to some of Chicago’s top attractions, including Millennium Park, the Art Institute of Chicago and Soldier Field, its cumulative 319 acres is coined “Chicago’s Front Yard”. There’s much to do within its boundaries, such as the annual Chicago Marathon and Taste of Chicago Festival. Still, if you’re simply looking to unwind, there are plenty of quiet corners for you to hide in.
Seek the stars at Adler Planetarium
The texture angles and capped dome of Adler Planetarium sits like a button that will open the doors to the universe. A landmark of Museum Campus that edges water with a Skyline Walk, it also presides over the Chicago skyline. Within this solid structure are captured displays of the Solar System and exhibits that detail the history of star-gazing, sharing what has been discovered about the universe so far. It also gifts a filtered view of the Chicago sky, erasing light pollution to reveal the star studded expanse. The Planetarium also hosts events when other planets come in view, presenting the mysterious at closer distance.
Scale up the Willis Tower Skydeck
Not all skyscrapers are made equal in Chicago, and Willis Tower beats the rest with a 25-year title of ‘world’s tallest building’. Standing at 442 meters and a Skydeck at 412 meters, its view glances over four states of sectioned concrete. Walk slow to the elevator and watch the movie documenting how Willis Tower came to be, and learn about other worthwhile Chicago architectures. Your Willis Tower Skydeck experience doesn’t end at stunning views; the four all-glass boxes of The Ledge will have you screaming at the sheer drop some 100 storeys to ground.
Refill on zen at the Garfield Park Conservatory
Palms, ferns, succulents and cacti – all the greens gathered under this beautiful garden under glass. Eight indoor display groves make up the Garfield Park Conservatory, a botanical paradise conceived as early as 1908. Whether it is the softer lushness of the Fen Room or dry brushes of the Desert House, the carefully sculpted spaces will make your stress melt away. Free up some time to participate in free yoga session or to watch gardening demonstrations; you don’t need to be in constant motion just because you’re on holiday.
Wander around the Navy Pier
Jutting out where Chicago Portage meets Lake Michigan, the Navy Pier is a heavy-duty tourist attraction that offers multifaceted entertainment. Occupying six blocks of land mass, it is a massive 50 acres of pier! You’ll find splashes of green at the botanical garden Crystal Gardens, fairground amusements around the Centennial Wheel and Funhouse Maze, the Chicago Children’s Museum and other sensory fun. The Miller Lite Beer Garden will let you wash down craft beers with live music; and to satisfy your drama-seeking needs, the Chicago Shakespeare Theatre is at the ready.
Get dramatic at Chicago Shakespeare Theatre
Fill up on drama at the non-profit Chicago Shakespeare Theatre down at Navy Pier. Celebrating the works of Shakespeare with remarkable productions on-site and off-site, the company has earned three Laurence Olivier Awards over the years. The theatre itself hosts two halls, the bigger one capable of sitting 510 audiences. Catch classic productions like Macbeth and Hamlet, or go light with a fun Peter Pan musical. It’s a relaxing activity to fill up your post-dinner schedule.
Scope around Lincoln Park Zoo
Visit Lincoln Park Zoo for free; in fact, it is one of the only free admissions parks left in the United States. Born in 1868, this zoo undergoes constant revamps to provide the best habitats for is thousand-strong residents. Gaze at lounging polar bears, grazing gazelles, ostriches and hot-spring loving Japanese macaques. Families in particular will love the petting zoo as you get close up and friendly with these incredible animals.
Lounge along Oak Street Beach
You don’t have to go far for some waterside chilling; Oak Street Beach stretches along the shore of Lake Michigan on North Lake Shore Drive. With the city right behind you and water in front, you get the best of both worlds. Heal under the sun with a quick swim, or rent chairs and kick back with a drink in hand. There are lifeguards keeping things fun and safe so go crazy with the splashing around! There are also bars and food joints nearby when you need fuel. Spend a relaxing afternoon here.
Attend to the Chicago Cultural Center
Having jumped careers from public library to being the country’s first municipal cultural center in 1991, Chicago Cultural Center touts a diverse “why you must visit” checklist. For one, it hosts thousands of exhibitions and programs over the year, ranging from music, theatre and film screenings to family-oriented events. The building itself speaks heritage, the interior boasting marbled pillars, polished brass work and hardwood from its 1897 conception. If the tiled archways aren’t enough to hold your attention, then its south and north domes surely will. Look up at the peerless stained glass Tiffany dome and the intricate Renaissance-style dome in appreciation of their fine workmanship.
Break boundaries at Maggie Daley Park
Challenge your physical boundaries at the dynamic Maggie Daley Park. Named in memory of the city’s former first lady, this relatively new recreational space sits a corner of Grant Park. Its unusual landscaping is attributed to architect Michael Van Valkenburgh, whose design stresses on an unconventional play area for both adults and children. Among the ice skating ribbon, picnic nook, mini golf course and so forth sectors, the Play Garden stands out. Offering six zones of fun, it features a Watering Hole and Enchanted Forest where giant marine creatures and mystical trees are brought to life.
Get pumped at United Center
Professional hockey, basketball and top-selling pop acts have blessed the halls of United Center. Serving as home turf for the Chicago Bulls and Blackhawks during on-seasons, this venue doubles down on rock and pop concerts the other months. While it may no longer be the headliner venue it once was, United Center still plays host to major pros. If you’re simply passing by, remember to grab a photo with Michael Jordan’s statue out in the public atrium.
Visit the Historic Pullman Foundation Visitor Center
When we say visit the Historic Pullman Center, we mean start your South Side tour here. Introducing George Pullman’s neighborhood (built to house his employees) through a series of exhibits, the visitor center provides context on the area’s significance. Once equipped with some knowledge of the neighborhood’s growth and preservation, set out on a self-guided tour to find film-featured historic buildings.
Consumer delights along the Magnificent Mile
Magnificent Mile brings you everything ‘big city’ in an 8-block whirl of shopping, dining and urban display. Stroll down Michigan Avenue for your choice of cuisine and retail, which covers indie boutiques to high-end flagship stores. Budget eats and fine dining are layered over each other, weaved in-between your shopping haven. But remember to turn your eyes up over the architecture as well! Try and spot the Tribune Tower, Wrigley Building and 875 N Michigan, all iconic landmarks within the Chicago skyline.
Touring The Art Institute of Chicago
Art lovers will be familiar with the names of Nighthawks, American Gothic and A Sunday Afternoon on the Island of La Grande Jatte – three celebrated works currently inhabiting the Art Institute of Chicago. Outside of Paris, here dwells the largest Impressionist and Post-Impressionist painting collection, featuring Monet, Cezanne, Renoir and van Gogh. Modernist contenders such as Pollock and Warhol, and designs by Frank Llyod Wright are also highlights of this institution. You can expect more than just paintings too; there are a wide range of Greek, Egyptian and Etruscan artefacts that run from mosaics to bronze items.
Catching the blues at Kingston Mines
When in Chicago, live music is a must. Dip by Kingston Mines for some of the city’s best blues music; it is the oldest and largest operating blues club still thriving soulfully. From night until dawn, energetic bands will have you swinging to their beats. If Kingston Mines isn’t quite your venue, there are over 200 live music stages for you to browse through. Definitely pencil this into your itinerary; it’s worth forgoing sleep.
Take a River or Lake Cruise
Lake Michigan and Chicago River offers a unique way of seeing the city. Embark on a tour through the city-crossing channel to spot some of Chicago’s architectural masterpieces. Ranging from 45 minutes to a sedate 75-minute long cruise, you have a selection of sightseeing trips with expert commentary. Check out the Classic Lake Tour, Architecture Cruise or Chicago River Architecture Cruise and compare their list of pass-by attractions.
Play old gamers at Logan Arcade
Arcade bars are common enough in Chicago, but few beat Logan Arcade’s well-preserved collection of game machines. Housed inside a refurnished hardware store, the nostalgic and down-to-earth vibe is supported by old-time classics such as Pac-Man. Mario Kart and Jurassic Park shooter games lure in younger, more modern crowds, whereas timeless pinball machines draw the various period selections together. There’s even a bar to supplement with craft beers and cocktails for those who need an extra kick.
Crossing The 606
You might not consider this a conventional attraction by any means, but The 606 is both functional and visual. An abandoned elevated railway track turned pedestrian and bicycle path, it is a 2.7 mile trek that links Logan Square, Humboldt Park, Bucktown and Wicker Park. It is a great location for “follow me” selfies and a long sight-seeing stroll.
Laugh away at Second City
Second City is comedy done right, birthing many comedians that have come to conquer this entertainment genre. Alumni include Tina Fey, Steve Carell, Stephen Colbert and Amy Poehler; current members of this company are equally talented. If you’re in need to some cheer-me-up, why not treat yourself to some sketch comedy and improv acts?
Delve into the past with Chicago History Museum
This brownstone building digs deep into Chicago’s history, delineating its origins, struggles, transformation from outpost to metropolis. Peruse the hall of Facing Freedom to grasp Chicago’s role in the fight for freedoms; it recounts the Civil War, Women’s Suffrage movement and the rise of labor unions between mid-1800s to 1970s. But there’s more – experience an old-time jazz club first hand, and sit in Chicago’s first L train. Merging historical displays with interactive cultural galleries, Chicago History Museum seeks to provide a comprehensive understanding of the city’s rich heritage.
Admire the Robie House
What’s so special about a house anyway? Well, learning that this home was designed by renowned Frank Lloyd Wright might change that cavalier attitude. If the narrow red bricks haven’t given it away, the Robie House is the perfect representative of early 20th-century Prairie style residences. Drawing inspiration from the spacious Midwest, this architecture makes use of open spaces, layered roofing, broad eaves and balconies. In contrast, the use of art-glass and careful selection of furniture fittings and fireplaces evoke a cozy vibe in complement of its warm coloring.
Catch a game at Wrigley Field
The Major League’s second oldest ballpark is surprisingly located in a residential neighborhood, and it is not car friendly either. Built in 1914, it is recognizable by its unassuming exterior and ivy-clad outfield walls – although its manual scoreboard steals the limelight. Its proximity to Lake Michigan makes the games doubly exciting as the wind factor sends balls careening off target, but home team Chicago Cubs thrive on the thrill anyway. Treat yourself to a game and round off the experience with a Chicago hot dog on hand as you cheer the players on.
Bar hopping in Boystown
That’s right; Chicago’s hottest LGBTQ neighborhood is calling the boys (and girls) to town. If you’re in search of good grog and even better company, hustle your way through Boystown by thoroughly exploring the drinks menu of every watering hole. From drag-show bars to fancy cocktail venues, you are guaranteed a night of laidback revelry.
Double the magic at Music Box Theatre
Yes, we know we’ve recommended great theatres already, but what is one more to the list? The old-school green signboard is only a taste of what awaits inside; an ornamental and retro movie palace that stayed in 1929. Divorce mainstream Hollywood films and popcorn your way through Music Box Theatre’s art-house films and documentaries instead. The real buttered popcorn is simply yummy toppings on top of midnight screenings, cult classics and director Q&As.
Hop on a Mob and Crime Bus Tour
Don’t even try to deny your interest in Chicago’s prohibition-era gangs. Al Capone, Bugs Moran and Dion Johnny Torrio may be big names but there are a lot more to the mob decades of 1920s and 1930s. Learn more about the city’s dark edge on a guided tour, where local historians will bring you to the site of the infamous Valentine’s Day Massacre and other notable neighborhoods.
Tread carefully in Stony Island Arts Bank
Did you know that Stony Island Arts Bank was purchased for $1 and transformed into an art and media archive? It’s a miracle what one measly dollar could do; the Bank is now home to 60,000 glass lantern slides and DJ Frankie Knuckles’ record collection. The bizarre (but somewhat logical) galleries feature world-famous artists as well, and guests are carefully lectured before allowed to wander around. Libraries are sacred after all, and you’ll certainly agree after seeing the teeming tower of books.
Get curious at the Museum of Science and Industry
Looking like a Greek pantheon along waterfront, the Museum of Science and Industry is nestled in the 1933 Old Palace of Fine Arts. If you find its hulking structure inspiring, you’ll be blown away by the mind-boggling exhibits within the walls. Some highlights include a World War II German U-505 submarine and commercial aviation pioneer Boeing 727. Complex scientific concepts are broken down for easy digestion in the Science Storms exhibit, whereas the coal mine replica take you back in time to earlier industrial sets.
Treat your ears at the Symphony Center
Close your eyes and throw away all other distractions to appreciate a filling, resonant performance by one of the world’s most prestigious classical ensembles. Featuring arrangements by the Chicago Symphony Orchestra and guest soloist, the shows are worth every dollar. Settle in the Grainger Ballroom, Buntrock Hall or Orchestra Hall for an ear-changing night at this historical landmark.