The 50 best things to do in Chicago right now

What is it? A free 45-minute walking tour in the heart of downtown.

Why go? Experience the wealth of public art decorating the city through the eyes of an expert. Each tour is led by a docent and covers a half-mile, beginning outside the Chicago Cultural Center and ending in Millennium Park. Throughout the tour, the docent offers context about each piece and its artist.

Don't miss: Before you embark on the tour, browse the wares at Buddy, the Chicago Cultural Center's hyper-local gift shop. 

What is it? Kayak Chicago sends you paddling along the Chicago River from a dock located just north of Goose Island.

Why go? After a few quick lessons, you'll be ready to set out on a self-guided river tour in a kayak. You can rent your boat by the hour or pay a flat fee to take it out for the entire day and check out changing leaves along the water.

Don't miss: A handful of guided excursions that highlight Chicago architecture or simply allow you to navigate the river at night.

What is it? Plucking fruit straight from the source.

Why go? With over 10 nearby apple orchards to choose from, there's no shortage of day trip and quick picking opportunities this fall. If you're craving caramel apples and a good maze, visit All Seasons Orchard. For a wealth of activities—like a petting zoo and corn maze—to go with your apple-picking adventure, hop over to Indiana's County Line Orchard.

Don't miss: Enjoy a variety of fall activities—like corn mazes, haunted houses, and drive-in movies—featured in our Fall 2025 Things to Do guide.

What is it? Expanded and updated in 2015, this riverside walkway hosts restaurants, bars, boating docks and plenty of spots to sit and admire the views.

Why go? Like everything else downtown, the Riverwalk can be pricey, but you can't beat the views when you snag a glass of vino at City Winery or enjoy some local grub at Chicago Brewhouse. Several boat tour also have launch points along the Riverwalk, if you prefer to get out on the water.

Don't miss: Post up at the Riverwalk nightly at 8:30pm and 9pm to catch Art on theMART, the 25-story light projection show across the water.

What is it? Exactly what it sounds like—a terrible portrait drawn by local artist Jacob Ryan Reno.

Why go? Reno has gone viral for his $5 terrible portraits, drawn in “five terrible minutes.” Every Sunday, Reno camps out at the Logan Square Farmers Market along the 606 trail—equipped with a meager folding table, a sketchbook and a box of markers. The caricatures he creates aren't just a much-needed dose of levity—they're also a beacon of authenticity in an optimization-obsessed world.

Don't miss: Of course, don't pass up strolling through the Logan Square Farmer's Market, where you can buy anything from locally grown veggies to thrifted clothing.

What is it? Chicago celebrations in honor of the famous German beer festival.

Why go? Chicagoans don’t need a reason to drink but will gladly raise a stein to Oktoberfest. There are events throughout the month of September and October all over the city, so ‘tis the season to get your fill of suds, brats and pretzels. Prost!

Don’t miss: The biggest Oktoberfest party every year at Lakeview’s St. Alphonsus church, which takes place this year on September 27-29.

What is it? Día de Muertos: A Celebration of Remembrance, the National Museum of Mexican Art's multimedia exhibition celebrating one of Mexico’s most extraordinary traditions.

Why go? Along with the Día de Muertos exhibition, explore a 6,000-piece permanent collection, performing-arts showcases and educational programming that represents an illustrious Mexican culture. After you've toured the exhibition, make your way to the museum's courtyard space, which will house an installation designed and curated by the youth artists of Yollocalli Arts Reach. 

Don't miss: End your visit with a moment at the community ofrenda—add a note, drawing or memory to honor someone you’ve lost and be part of this collective tribute. 

What is it? A world-renowned orchestra.

Why go? Considered one of the leading orchestras in the United States, the CSO plays a variety of enthralling music and hosts touring soloists and small ensembles as well. During fall to spring, Symphony Center is home to the CSO. 

Don't miss: Watch your favorite flicks like never before—with a spellbinding live score—during the “CSO at the Movies” series.

What is it? A West Town cafe-meets-gift shop that looks like it was designed by Wes Anderson.

Why go? Step inside and you're greeted by a velvet-upholstered counter, sticker-covered clipboards and sleek, futuristic-font signs declaring that the space is "not a cult." Cake-shaped candles, fluorescent tea boxes and handmade ceramics are artfully arranged on shelves and tables, every detail carefully curated. With a menu stacked with delectable drinks—like the Sugoi Strawberry Matcha—you'll never want to leave.

Don't miss: The Rawson pop-up shop—overflowing with vintage workwear, elevated basics, bespoke charms and more—in COE's back room. 

What is it? “Patterned by Nature,” the Chicago Botanic Garden's newest exhibition.

Why go? Through meticulously planted gardens and nature-inspired art installations, “Patterned by Nature” highlights the intersection between graphic design and horticulture. Think succulent gardens forming paisley patterns and daisies arranged into tartan motifs.

Don't miss: Rachel B. Hayes's Ebb and Flow and Radiate—a vibrant, quilt-inspired installation—hovering over the Bonsai Court.

What is it? A weekly 75-minute yoga class held in the Judy Istock Butterfly Haven, a greenhouse brimming with tropical plants and over 75 species of exotic butterflies and stunning birds.

Why go? Experience nature like never before with a beginner-friendly yoga class in one of Chicago's hidden gems. Find your flow surrounded by over a thousand butterflies and birds flying around (and sometimes on) you. After class, wander through lush flora and tropical trees that will make Chicago feel half a world away—if only for a little while.

Don't miss: Stick around until 2pm for the museum's daily “First Flight Butterfly Release.” 

What is it? 'Scopes in the City, the Adler Planetarium's free telescope observing program.

Why go? For over a decade, the Adler Planetarium has been popping up at libraries, restaurants, bars and parks around the city with telescopes in hand. Passersby are encouraged to look skyward with astronomers and discuss their findings. Depending on the turnout, you might even luck out with a hands-on activity too.

Don't miss: A special moon observation session at the Chicago Public Library's Uptown Branch on September 30.

What is it? The Newberry Library, founded in 1887, is an independent research library located right in the heart of the Gold Coast.

Why go? From illuminated medieval manuscripts to the personal papers of local authors, the Newberry is home to an impressive collection of work that is free to access. The library hosts exhibitions, theatrical performances, lectures, seminars, workshops and more. 

Don't miss: Sign up for a free tour of the Newberry's current exhibition, Winging It: A Brief History of Humanity’s Relationship with Birds, which chronicles avian history through a cultural lens.

What is it? Cake and cookie decorating workshops taught by celebrated pastry chefs.

Why go? We're probably not alone in wanting to make an intricately decorated, Instagram-worthy cake, and Bon Vivant will give you the skills to elicit ooohs and ahhhs from your friends. After feasting on snacks and cocktails, a team of experienced bakers offers tips, tricks, and techniques for creating your own creative confections. Plus, you get to take your edible artworks home.

Don't miss: Bon Vivant's Happy Hour offerings, with themes like “Taylor Swift” and “Tini Time.”

What is it? A formerly abandoned stretch of elevated railway track named after the first three digits in every Chicago zip code. 

Why go? Looking for a convenient way to get between Logan Square, Humboldt Park, Wicker Park and Bucktown? This is it. The 2.7-mile path was spruced up by the city and turned into a functional attraction that delights locals and visitors.

Don’t miss: Local artist Jeff Zimmermann's colorful Conagra Mural (Urbs in Horto) just across the Milwaukee Avenue bridge, which acknowledges Chicago's agricultural legacy.

What is it? A bright and airy brewery specializing in saison-style beers.

Why go? Since staking their claim on Ravenswood’s flourishing “Malt Row,” Is/Was Brewing has emerged as an authority on saison-style beers. Their success has echoed far beyond Chicago, too—recently being crowned one of the top saison producers in the world by Craft Beer & Brewing.

Don't miss: Weekly Trivia Tuesdays with QuizzDaddy Trivia and Bingo Thursdays.

What is it? A lovely meal outside in a public park.

Why go? Make the most of summer by packing a basket full of food and beverages and heading to a nearby park. Chicago's motto is "City in a Garden," and our public green spaces live up to such a lofty name. With more than 600 facilities throughout the city, you won't have to wander very far to find a spot for a picnic.

Don't miss: Set up shop at Ping Tom Memorial Park to feast your eyes on over 17 acres of Chinese-inspired landscaping.

What is it? This smoke shack was born when the steel industry was thriving and the area was populated by hungry day laborers.

Why go? Located near a bridge featured in The Blues Brothers just west of the Indiana border, Calumet Fisheries slings smoked shrimp, trout, sable and more. There's no seating inside, so you'll need to take your paper bag full of seafood outside, where you can find a spot along the bridge to chow down or just eat it inside your car. 

Don’t miss: Don't forget to get some crackers and coleslaw to pair with your expertly smoked fish.

What is it? An 18-hole miniature golf course located in Maggie Daley Park.

Why go? There's a kitschy kind of charm to mini-golfing in the shadow of the Chicago skyline, especially since the course is decorated with replicas of famous Chicago attractions (like a six-foot-tall Willis Tower and a teeny version of the Picasso sculpture in Daley Plaza). 

Don’t miss: Snapping a photo next to the mini Chicago landmark of your choice.

What is it? A 90-minute, dog-friendly boat ride on the Chicago River and Lake Michigan.

Why go? Tired of the same old architectural cruise? Then liven things up with some pooches! First Lady offers a canine cruise every weekend, where you’ll be surrounded by four-legged friends as you take in unparalleled views of the skyline and learn about the city’s rich history. Plus there are plenty of photo ops, of course.

Don't miss: Howl-O-Ween, a special October cruise complete with pumpkin dog treats and a doggie costume contest.

What is it? A storied 5am dive with a killer jazz jukebox, no-nonsense attitude and the most conversation-inducing bar art in the city.

Why go? Knock back stiff drinks with a gloriously diverse cast of characters from grizzled old timers to tourists from nearby Second City at this late-night watering hole. It’s a favorite of many cultural icons, from the late Anthony Bourdain and actor Michael Shannon (he watched the Oscars here in 2018) to Chicago film critic Roger Ebert—and should be a fave of yours, too.

Don’t miss: The bar is decked out with nudie paintings of famous politicians like Sarah Palin and Rod Blagojevich by Bruce Elliott, the establishment’s longtime owner.

What is it? The sweetest spot for indulging your sweet tooth.

Why go? This iconic far South Side shop, immediately recognizable by its bright pink exterior, has been making ice cream-ordering decisions easy since 1926 thanks to their namesake Rainbow Cone. The classic sugar cone is topped with colorful layers of chocolate, strawberry, Palmer House (New York vanilla with cherries and walnuts), pistachio and orange sherbet ice cream.

Don’t miss: If you’re still in need of another sugar rush, know that Rainbow also makes cakes, sundaes and shakes. 

What is it? A pinball palace located in the Salt Shed's former boiler room (owned by none other than Jim Zespy of Logan Arcade).

Why go? Housing over 100 games, 8-bit purists, pinball wizards and casual gamers will all find fun ways to collect virtual prize tickets, which can be redeemed at a fully-stocked prize shop. Billed as an all-ages space by day and adult-centric playground—complete with jello shots—by night, there's something for everyone at Elston Electric.

Don't miss: Regular Pinball League Nights, where groups of four duke it out for concert tickets, game cards and more.

What is it? "Tropic Like It's Hot!," an afternoon of boozy tea-infused cocktails at The Gwen Hotel.

Why go? This weekly event is a far cry from the tea parties of your childhood. The Gwen has put their own cheeky twist on tradition tea time with live DJs, rotating snacks and bottomless boozy (or spirit-free) tea-infused cocktails.

Don't miss: If you want to keep the fun times going into the night, indulge in the Moët & Chandon champagne vending machine in the fifth floor lobby.

What is it? Guarded by an iconic pair of bronze lions, the Art Institute of Chicago houses a permanent collection of more than 300,000 artworks. 

Why go? The Art Institute of Chicago is filled with masterpieces from every era, from Georges Seurat’s iconic painting A Sunday on La Grande Jatte (notable for its appearance in Ferris Bueller’s Day Off) to Andy Warhol's print of actress Elizabeth Taylor. 

Don’t miss: Catch the new exhibit Gustave Caillebotte: Painting His World, which features a body of work by a titan of the Impressionist movement.

What is it? A gorgeous glass structure home to more than 100,000 plants. 

Why go? When temps start to dip, there are few better places in Chicago to escape the cold than Garfield Park Conservatory, where you can wander through eight indoor display gardens full of greenery. Marvel at towering tropical plants in the 65-foot Palm House, admire cacti in the Desert House and imagine the primordial settings of Illinois millions of years ago among the lush Fern Room.   

Don't miss: Swing by Horticulture Hall from Friday through Sunday for a lavender oat milk cold brew made by Monday Coffee Co., the conservatory's resident coffee pop-up.

What is it? Where Bill Murray, Tina Fey, Gilda Radner, Chris Farley and Steve Carell cut their comedic teeth. 

Why go? Before they joined the cast of Saturday Night Live or became big-screen stars, those folks above practiced their craft on the mainstage at the Second City. The venue's premiere revue features some of the institution's most talented performers in a series of loosely-connected, topical comedy sketches.

Don't miss: Itching to take the stage yourself? Sign up for a class at the Second City Training Center.

What is it? One of the last free zoos in the country, this 35-acre attraction connects visitors with animals from all over the world.

Why go? More than 1,000 critters are waiting for you to visit them—free of charge—in Lincoln Park. From mammals (beavers, lions, otters and bears) to birds (penguins, eagles and parrots) to reptiles (snakes, crocodiles and turtles), there's something for every animal lover. 

Don’t miss: The expansive Regenstein Macaque Forest, where snow monkeys swing from branch to branch. 

What is it? Alfresco dining season.

Why go? We only get a few precious months of outdoor dining in Chicago, so make the most of it while you can. Live your best life at the city's top patios, terraces and rooftops, which afford great food and drinks, fun vibes and plenty of sun and breeze.

Don't miss: End your alfresco dining experience at Middle Brow Brewery and Winery with a healthy portion of self-serve soft serve. 

What is it? The observation deck on the 103rd floor of the third tallest building in the U.S. 

Why go? If you're looking to see more of Chicago than you'd be able to take in on a walking tour, the Skydeck is your best bet. On a clear day, you can see up to four states and 50 miles out. The Skydeck's main attraction, The Ledge, features glass boxes hanging out over the building, offering a thrilling experience and even better views from 1,353 feet off the ground. 

Don't miss: Pie in the Sky, the Skydeck's dining experience that includes a three-course meal catered by Giordano's.

What is it? The best spas for a day of rest and relaxation.

Why go? Summertime's non-stop activities and sunshine can wreak havoc on our skin, which is a prime reason to escape the heat and rejuvenate with a visit to a spa. The city's top spots offer everything from luxurious treatments to tried-and-true massage therapy, and there's something for every budget. After all, a little self-care can go a long way.

Don't miss: Follow up a treatment at Bucktown's Spa Soak with an indulgent meal at the original Small Cheval, located just across the street.

What is it? Hiking trails around Chicagoland.

Why go? Now that it's warm out, it's the perfect time to go hiking. Visit a state park or nature preserve for an adventurous escape from the city. These sprawling, winding paths will take you through historic sites, sand dunes, woodlands and much more.

Don't miss: Try your luck at spotting roaming buffalo at Buffalo Rock State Park—just a two-hour drive from Chicago.

What is it? An ace place to lose it to house music, right in the city that invented the genre. 

Why go? In the ’80s, Chicago served as the epicenter of the creation of a new sound that still influences the work of modern hip-hop and electronic artists. If you want to experience house music, there's no more authentic environment than Smart Bar. Within the subterranean Wrigleyville club, skilled DJs, drag performers and sweaty revelers come together to the steady pulse of a house beat.

Don’t miss: The crowded Queen! dance party, which takes place nearly every Sunday night.

What is it? Designed by activist and artist Yoko Ono, Skylanding is composed of 12 large steel lotus petals jutting from the ground of the Garden of the Phoenix in Jackson Park.

Why go? Calling all public-art fanatics. This gleaming installation from the famed artist has become a major draw in the 600-acre park. The photogenic sculpture was erected as a symbol of peace, taking up residence on the site of a pavilion built by the Japanese government for the 1893 World’s Columbian Exposition.  

Don’t miss: The park is also home to a beautiful, traditional Japanese respite dubbed the Garden of the Phoenix. 

What is it? An Uptown institution that books smart bebop and free jazz with a discriminating ear. 

Why go? In the ’20s, Chicago gangsters like Al Capone were known to frequent the Green Mill, but ever since Prohibition, the club has garnered a reputation for hosting live jazz every night. 

Don’t miss: Taking a picture under the glittering marquee, which wasn't actually destroyed in Michael Mann's 1981 neo-noir film Thief. 

What is it? A ’40-era drive-in that still sends uniformed servers to your car, delivering hot dogs, burgers, milkshakes and more fast food delights.

Why go? As its name suggests, Superdawg specializes in Chicago-style hot dogs, which add piccalilli and a pickled green tomato to the usual array of toppings. Every super dish comes in a cute box (usually on a bed of crisp French fries) and can be ordered from your car or at a walk-up window.

Don't miss: Try the Superonionchips instead of the Superfries—they're like onion rings, but better.

What is it? The city’s quintessential hipster dive.

Why go? Situated near a stretch of Ukrainian Village that constantly churns out shiny new bars and restaurants, Rainbo Club is an incorruptible constant of cool. The red neon sign beckons from blocks away, pulling patrons into its no-frills, no-bullshit space to down a shot and a can of something cheap in its coveted red booths.

Don’t miss: A visit to the photobooth, a Chicago rite of passage that dates back decades before Instagram was a thing (Liz Phair was a fan).

What is it? A massive natural history museum that was founded to house the biological and anthropological collections for the World’s Columbian Exposition of 1893. 

Why go? With 350,000 square feet of permanent exhibitions to explore, deciding what to see at the Field Museum can be a daunting task. We recommend starting in the institution's new Reptiles Alive! exhibit, where you'll explore the lives of reptiles with immersive activities and, of course, 20 live reptiles on view.

Don’t miss: The Grainger Hall of Gems, a breathtaking collection of more than 600 gemstones and 150 pieces of antique and contemporary jewelry.

What is it? A popular movie theater chain from Texas.

Why go? In addition to showing the latest films, the venue offers expansive food and beverage menus and servers will bring meals to customers' seats during screenings.

Don't miss: The theater's special events, which include rowdy sceenings where talking is encouraged and movie parties—immersive and interactive viewing experiences featuring fun props, themed drinks and more.

What is it? A string of art galleries located on Chicago Avenue between Ashland Avenue and Wood Street. 

Why go? A combination of favorable real estate, happenstance and collaborative spirit has drawn some of Chicago's finest galleries—including Matthew Rachman Gallery, DOCUMENT, Rhona Hoffman, Chicago Truborn and many others—to this multi-block stretch in West Town, creating a concentrated (and not to mention, free) tour of curated work. Plan an afternoon around the exhibitions that pique your interest, and don't forget to make a reservation at each gallery ahead of time. 

Don’t miss: Looking to splurge on, say, a mid-century Danish sofa or a luxury cowhide rug? Make an appointment at Matthew Rachman Gallery to view the furniture collection available for sale, where you'll find items from iconic designers like Vladimir Kagan, Jens Risom and Eero Saarinen.  

What is it? A 16-mile paved trail beginning in Gompers Park that takes riders all the way to the Chicago Botanic Garden.

Why go? If you're craving a quick escape from the city on your bike, you can take the North Branch Trail to attractions throughout the northern suburbs. Have a beer at Hubbard's Cave, get a pie at the Pequod's in Morton Grove or relax in the Erickson Woods in Winnetka.

Don't miss: The four-mile loop trail through the Skokie Lagoons (which can also be used to get to the Chicago Botanic Garden).

What is it? A neighborhood that serves as one of the primary hubs of Chicago's Chinese community, filled with restaurants, shops and incredible nods to East Asian architecture.

Why go? Chinatown is a great place to mosey from shop to shop and spend some time outdoors, whether you're walking through Chinatown Square or admiring the sweeping skyline views from Ping Tom Memorial Park. 

Don't miss: Dumplings from QYX, bubble tea from the walk-up window at Joy Yee, Peking duck from BBQ King House, cocktails at Nine Bar... the list goes on. Start at Chinatown Square and work your way south down Wentworth, passing under the street's famous gate and into its central commercial strip.

What is it? One of the best places to sit on a rock and look at tall buildings from afar.

Why go? Just north of the Museum of Science and Industry, this man-made peninsula is a short jaunt from the Lakefront Trail. When the sun is out, it's a beloved spot for picnics, lounging and canoodling on the rock steps that line the perimeter of the point.

Don’t miss: The Promontory Point Field House, an extremely popular wedding venue that looks like a miniature castle.

What is it? A collection of murals and street art on an old railroad embankment in Pilsen that stretches from the Chicago River to Western Avenue.

Why go? Take a stroll across 16th Street and you'll spot murals by local artists like JC Rivera and Hebru Brantley as well as international talents like The Yok and Sheryo.

Don't miss: An infamous painting of a severed possum by Belgian street artist ROA, located just west of 16th and Laflin Street.

What is it? A worker-owned bookstore, offering new and used books for in-store browsing and curbside pickup.

Why go? You can support a local business while chipping away at your reading list by ordering something from this Pilsen shop. Submit an order online or call and talk to a human during business hours if you need a recommendation.

Don't miss: Add a donation to the Liberation Library to your order to support the purchase of books for incarcerated youth.

What is it? A nearly 200-foot-high Ferris wheel.

Why go? You won't find many sights that can rival the ones from Centennial Wheel. Riders are treated to 360-degree views of the skyline and Lake Michigan while sitting in enclosed, climate-controlled gondolas.

Don't miss: After your ride, head to the Original Rainbow Cone at Navy Pier for a tasty sweet treat.

What is it? Chicago's only aquarium, home to thousands of colorful fish and other aquatic creatures.

Why go? Permanent exhibitions like "Wild Reef" and "Amazon" allow you to gaze at fish, stingrays, an anaconda and sharks. But the interactive experiences may be the biggest draw, allowing visitors to get up close and personal with some of the animals that live at the Shedd Aquarium and learn more about them.

Don't miss: The internet-famous rockhopper penguins, known for exploring the Shedd (and other Chicago institutions) during lockdown in 2020. You can say hi to them in the Polar Play Zone exhibit.

What is it? A Wicker Park destination for discerning record nerds.

Why go? The "dusty grooves" of course refer to the wonderous global rhythms found in the smartly curated bins, sorted into Tropicalia, Afrobeat, reggae, vintage soul, French pop, blues, jazz and other genres. 

Don’t miss: Obscure titles that you'll have a hard time finding elsewhere in the city.

What is it? A love letter to all things magic hidden behind what appears to be a laundromat.

Why go? After three years of performances at Uptown Underground, the Chicago Magic Lounge’s brick-and-mortar manifestation opened in early 2018. The spot sports three performance spaces. There’s the front bar, where you can enjoy a drink and some sleight-of-hand. Then there’s the 120-seat Blackstone Cabaret mainstage, where ticketed shows take place, as well as a smaller back room, dubbed the 654 Club, offers up-close magic.

Don’t miss: While enjoying your cocktail in the bar, check out the magician’s table built into the center of the bar itself.