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Photograph: Shutterstock/Jess Kraft

The 55 best things to do in Chicago right now

Discover the best things to do in Chicago, from iconic meals and views to cultural musts and late-night shenanigans

Edited by
Emma Krupp
Written by
Tim Lowery
,
Zach Long
&
Jay Gentile
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September 2022: And just like that, it’s fall in Chicago again! Dive head first into a new season with apple picking, corn mazes and the first signs of fall foliage, or prep for Halloween with visits to the spookiest haunted houses near Chicago (most of which open their doors by late September). And if you prefer to cling to the last vestiges of summer, soak up some more outdoor time at rooftop patios and the final few festivals of the season. 

No matter where your interests lie, you can always find something to get excited about in this no-nonsense Midwestern metropolis. The best things to do in Chicago run the gamut—from seriously fun to awesomely educational. Looking for culture? Spend a day exploring Chicago museums. Hungry? You've come to the right place, because Chicago is famous for its delicious cuisine. There are tons of amazing restaurants in Chicago that highlight the city's rich and diverse culinary landscape. (And plenty of uniquely Chicago bars that do the trick, too.) We've searched all across the city to assemble this list of the best things to do in Chicago. Follow it and never get bored here again.

Done something on this list and loved it? Share it with the hashtag #TimeOutDoList and tag @TimeOutEverywhere.

You can also find out more about how Time Out selects the very best things to do all over the world, or take a look at our list of the 50 best things to do in the world right now.

Time Out Market Chicago
  • Restaurants
  • West Loop

We've rounded up the best chefs in the city to join us at Time Out Market Chicago, a culinary and cultural destination in the heart of Fulton Market. The 50,000-square-foot space houses 18 kitchens, three bars and one drop-dead gorgeous rooftop terrace—all spread across three floors. Our mission is simple: Bring the pages of Time Out Chicago to life with the help of our favorite chefs, the ones who wow us again and again. You'll find delicious barbecue from chef D’Andre Carter at Soul & Smoke, creative burgers at Big Kids, fried chicken from Luella’s Southern Kitchen and extravagant milkshakes from JoJo's shakeBAR. If you're thirsty, sit down at one of the Market's bars to enjoy a menu of local beer, a robust wine list or a cocktail created in collaboration with Chicago mixologists. And keep an eye out for events, concerts and artwork within the Market throughout the summer—we're keeping our calendar packed with things to do.

Best things to do in Chicago

  • Museums
  • Art and design
  • Grant Park
  • price 2 of 4

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. This month, see Normandy depicted by renowned British painter David Hockney, who used his iPad to render springtime in bright colors for ”David Hockney: The Arrival of Spring, Normandy, 2020.”

Don’t miss: Tucked away in the lower level of the Art Institute, the Thorne Miniature Room contains 68 recreations of American, European and Asian architecture and furniture, represented at 1:12 scale. It’s like a hyper-detailed, ultra-realistic doll house that you wish you had when you were a kid.

  • Attractions
  • Parks and gardens
  • East Garfield Park

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

Why go? The Garfield Park Conservatory is best known for its eight indoor display gardens, and while those are undeniably spectacular, pleasant weather provides the perfect opportunity to explore the conservatory's 10 acres of outdoor landscaping. Stroll through a meditative labyrinth in the Sensory Garden, peer at your reflection at the glassy lily pool or take the kiddos for a romp around the Play & Grow Garden. 

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

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  • Bars
  • Cocktail bars
  • Uptown
  • price 2 of 4

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. After an extended hiatus, live concerts are back at the Uptown venue.

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

  • Things to do

What is it? The breeziest way to survey the city's famed architecture.

Why go? An architectural tour is a must for any visit to Chicago, and the Chicago Architecture Foundation employs certified volunteer docents who narrate the history behind more than 50 downtown buildings for the duration of a 90-minute cruise along the Chicago River.

Don’t miss: An evening version of the tour that allows you to take in the twinkling city lights from the river.

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  • Bars
  • Cocktail bars
  • Humboldt Park
  • price 1 of 4

What is it? A beloved Humboldt Park bar that reopened in February for the first time in two years. 

Why go? The Clipper's future hung in the balance when it shut down in early 2020 amid a rent dispute, but don't worry—Orbit Group, the bar's new operators, haven't done much to change the place save for a few minor decorating upgrades. 

Don’t miss: Order a cocktail and retire to "The Little Clip," a new dance lounge located in the former C.C. Ferns space that pays homage to Danny's (the defunct Bucktown bar where some of the Clipper's current staff once worked) with a lineup of DJ nights. 

  • Sports and fitness
  • Kayaking & canoeing
  • River North
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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.

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  • Museums
  • Science and technology
  • Museum Campus
  • price 2 of 4

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 popular "Inside Ancient Egypt" exhibit, where you'll descend into a recreation of the 5,000-year-old tomb of pharaoh’s son Unis-Ankh. From there, you'll walk through an extensive assemblage of Egyptian artifacts, including one of the largest collections of mummies in the U.S.

Don’t miss: Upon entering the Field Museum, come face to skull with Máximo, a 70-ton, 122-foot-long skeleton of a titanosaur. You can also visit SUE, the museum's T. rex skeleton, in the Griffin Halls of Evolving Planet exhibition.

  • Things to do

What is it? As late summer transitions into early fall, apple orchards in the suburbs and surrounding countryside welcome folks onto their premises for u-pick apples, hayrides, delicious baked goods and plenty more autumnal fun. 

Why go? Feeling melancholy about the end of summer? We’re pretty sure an apple orchard visit will perk you back up again. With dozens of apple varieties to choose from (including hard-to-find options like Sansa and Orange Cox Pippin) plus a heaping helping of kitschy dall decor, these local farms deliver everything you need to get excited about the start of a new season. 

Don’t miss: Before you head back to the city, grab a box of cinnamon sugar-dusted apple cider doughnuts.

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  • Museums
  • Art and design
  • Loop

What is it? Located just around the corner from Millennium Park, this gorgeous specimen of a building is the country's first free municipal cultural center; inside, you'll find tons of programming, exhibitions, and stunning architectural flourishes to explore, as well as a gift shop stocked with goods from local artists.

Why go? Anyone spending time in the Loop should make a point to check out any ongoing programming happening at the Cultural Center, which can run the gamut from art exhibitions to massive architectural expos. And did we mention it's completely free?

Don't miss: Once you've toured the 38-foot Tiffany glass dome in Preston Bradley Hall, head to the Landmark Gallery on the first floor to see "The Great Chicago Fire in Focus," an ongoing exhibition showcasing glass plate negatives depicting the ravages of the Chicago Fire.

  • Attractions
  • Historic buildings and sites
  • Hyde Park
  • price 1 of 4

What is it? A historic house that Wright himself called "the cornerstone of modern architecture." 

Why go? Nearby Oak Park may be a mecca for Frank Lloyd Wright enthusiasts, but you can see some of the architect's finest work without leaving the city. The Robie House in Hyde Park exemplifies Wright's signature Prairie School style, both in its external appearance and interior design. You can take a peek inside the historic home (and get some decorating ideas) by taking a tour led by the Frank Lloyd Wright Trust, offered five days a week.

Don’t miss: The bevy of beautiful art-glass windows and the furniture (also designed by Wright). 

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  • Attractions
  • Streeterville
  • price 2 of 4

What is it? A Willy Wonka-esque, multi-room, highly interactive experience dedicated to all things ice cream. 

Why go? It’s tempting to label the Museum of Ice Cream, which boasts two other U.S. locations and boundless Instagram cachet, as an overpriced tourist trap. Still, we think you’d have to be a grump not to find the candy-colored attraction at least a little charming. Visitors enter through a pink recreation of an El car that leads them to a collection of experiential rooms designed to cater to one’s inner child (and actual children), including a science-heavy ice cream lab, an exhibit on the history of local ice cream ventures, a mini-golf course and—of course—the museum’s famous sprinkle pool. Tickets will run you nearly $40, but they do include unlimited ice cream treats, so make sure you come hungry. 

Don’t miss: A controversial hot dog-flavored ice cream treat available in the mini-golf room. 

  • Things to do
  • Literary events
  • Pullman
  • price 1 of 4

What is it? This destination houses exhibits about the South Side 'hood's growth and preservation. 

Why go? When businessman George Pullman started a railroad sleeping car factory on the South Side of Chicago, he built an entire town to house his employees. The industrial complex has since been designated a National Monument and the Pullman Foundation Exhibit Hall is the best place to start exploring the area, especially if you want to join a guided tour on the first Sunday of every month from May through October.

Don’t miss: Set out on a self-guided tour of the district, which includes historic buildings featured in films like Road to Perdition and The Fugitive.

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  • Museums
  • Science and technology
  • Hyde Park
  • price 2 of 4

What is it? "The Art of the Brick," a touring exhibition that collects more than 100 Lego sculptures created by artist Nathan Sawaya.

Why go? To see recreations of Michaelangelo's "David," Da Vinci's "Mona Lisa" and a gigantic T.rex—all made from hundreds of thousands of tiny plastic bricks.

Don't miss: Once you've finished touring the Lego sculptures, check out the museum's revamped "Take Flight" exhibit, which features a section of a 727 jet that visitors can walk through.

Get high at 360 CHICAGO
  • Things to do
  • Streeterville
  • price 2 of 4

What is it? Set atop the building formerly known as the John Hancock Center, this observatory offers views of the city (and surrounding states) from 1,030 feet above the streets.

Why go? The sights from the 94th floor can't be beat, whether you're a longtime Chicagoan or a visitor. Stick around to enjoy a cocktail at 360 CHICAGO's bar or explore some of the interactive exhibits detailing the city's history.

Don't miss: 360 CHICAGO's most terrifying attraction: TILT. Guests board a glass-enclosed platform that slowly tilts over the side of the building at a 30-degree angle. Thrill seekers will want to fork over the additional fee for a ticket. 

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  • Music
  • Rock and indie
  • Ukrainian Village
  • price 1 of 4

What is it? The best damn rock club in the States.

Why go? For more than a quarter of a century, a gig at the Empty Bottle has served as a rite of passage for local and touring musicians. The nondescript club on the edge of Ukrainian Village is far from the biggest venue in town (capacity is around 300), but the folks who book it have a knack for landing rockers, electronic acts and experimental musicians on the rise. Grab an Old Style, find a spot on the stairs by the stage and take in a sure-to-be memorable show. 

Don’t miss: A slice of pizza before (or after) the show at next door's Pizza Friendly Pizza. 

  • Attractions
  • Public spaces
  • Armour Square

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... 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.

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  • Bars
  • Lounges
  • Wrigleyville
  • price 2 of 4

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.

  • Art
  • Public art
  • Lower West Side

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.

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  • Music
  • Folk, country and blues
  • Sheffield & DePaul
  • price 1 of 4

What is it? You have to listen to blues music when you’re in Chicago, and few places are as fun to see the blues as Kingston Mines.

Why go? The city’s largest and oldest continuously operating blues club features high-energy live blues bands performing on two stages until 4am Thursdays and Fridays and 5am on Saturdays. Whether you’re hanging with bleary-eyed tourists from Iowa or friends of the local blues guitarists on stage, it’s hard to have a bad time here.

Don’t miss: The cover grants you entry to both rooms and its two different stages.

  • Things to do
  • Literary events
  • Douglas

What is it? The college's Bronzeville campus is studded with one of the country's largest collection of buildings designed by Ludwig Mies van der Rohe, the German-born steward of the Bauhaus architecture movement in Chicago. 

Why go? Mies was a pioneering figure in American Modernism, and he completed some of his most significant work while serving as the director of the Department of Architecture at the Armour Institute of Technology. The sleek, column-free S.R. Crown Hall—which houses the present-day College of Architecture at IIT—is considered his masterpiece, and the college's entire campus has been inducted into the National Register of Historic Places. 

Don’t miss: You can always take a self-guided tour, but the Chicago Architecture Center offers two-hour guided sessions that lead visitors through the evolution of the campus, from Mies' heyday in the mid-20th century to the more recent McCormick Tribune Campus Center designed by Pritzker Prize-winning Dutch architect Rem Koolhaas.

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  • Art
  • East Village

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.  

  • Attractions
  • Parks and gardens
  • North Park

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).

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  • Things to do
  • Lincoln Park

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. 

  • Bars
  • Dive bars
  • Ukrainian Village
  • price 1 of 4

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).

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  • Attractions
  • Parks and gardens
  • Humboldt Park

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.

  • Restaurants
  • Eating

What is it? Located on the edge of Pilsen and Chinatown, 88 Marketplace is a multi-level Chinese grocery store stocked with all kinds of imported food and beverages.

Why go? The second-floor market isn't just a place to shop for ingredients—it also hosts an expansive food court, where you'll find sushi, Hong Kong-style barbecue, Vietnamese pho and Chinese baked goods. While it doesn't boast the sheer variety of dishes that you'll find while walking through Chinatown, it's an extremely convenient spot to sample various cuisines under one roof.

Don't miss: Swing by the brightly-lit pastry cases at Chiu Quon for a milk tea egg tart, a palm-sized confection with all the brown sugar toastiness of its namesake.

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  • Restaurants
  • Eating

What is it? An eye-popping Lakeview restaurant designed to make visitors feel as though they've entered the two-dimensional world of a comic book. 

Why go? These highly Instagrammable black-and-white café concepts originated in Malaysia before spreading to countries like Japan, South Korea and beyond—and while there are just a handful of 2-D joints in the U.S. right now, we're willing to bet they'll become a trend over the next year or so. 

Don't miss: Grab an order of the restaurant's pon de ring mochi doughnuts, which are irresistibly fluffy and just a little bit chewy.

  • Restaurants
  • Hot dogs
  • Norwood Park
  • price 1 of 4

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.

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  • Attractions
  • Parks and gardens
  • Millennium Park

What is it? The crown jewel of Chicago's front yard.

Why go? Home to iconic public art installations such as Cloud Gate (a.k.a. "The Bean"), this 25-acre park is one of the most popular gathering spots in the city. Visitors can walk through the vegetation in the Lurie Garden—renowned for its beauty throughout all of Chicago's seasons—or grab a spot in the sunshine on the Great Lawn. 

Don’t miss: Crown Fountain, an interactive installation featuring two 50-foot-tall LED video structures. 

  • Attractions
  • Zoo and aquariums
  • Museum Campus
  • price 3 of 4

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.

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  • Things to do
  • Hyde Park

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.

  • Nightlife
  • Uptown
  • price 2 of 4

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. 

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  • Theater
  • Interactive
  • Uptown
  • price 1 of 4

What is it? A theater where performance art is populist and fun AF. 

Why go? You never know what you'll see when you attend the Neo-Futurists' signature show, Infinite Wrench, but it's nearly always entertaining. The ensemble races against the clock to cram 30 miniature, two-minute plays into a 60-minute show that bristles with madcap energy. Over the course of the evening, you might witness a dramatic monologue, a funny song or simply stare at someone eating a sandwich. 

Don’t miss: Grab a seat toward the front of the stage if you're game for interacting directly with the show's performers (their plays occasionally call for audience participation). 

  • Restaurants
  • Contemporary American
  • Lincoln Park
  • price 4 of 4

What is it? Chef Grant Achatz’s three-Michelin-starred institution.

Why go? It's a triple-figure investment, but folks looking for fine dining in Chicago won't find a more awe-inspiring meal than Alinea's experimental tasting menu 

Don’t miss: The option to add a rare bottle of wine from the Alinea cellar or a bottled Aviary cocktail to your order.

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  • Comedy
  • Comedy clubs
  • Lincoln Park
  • price 2 of 4

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: Do The Right Thing, No Worries If Not, a two-hour comedy extravaganza from the venue's mainstage revue. 

  • Shopping
  • Liquor stores
  • Avondale
  • price 2 of 4

What is it? A place of worship for hops-heads.

Why go? You'll always find something new or unexpected on tap at this Avondale bar and bottle shop, which has gained a reputation for stocking the most sought-after releases from local and out-of-state brewers. 

Don’t miss: Follow the Beer Temple on Instagram to stay on top of what's newly in-stock. If you want to get your hands on the latest brews from Hop Butcher and other hard-to-find releases, you'll need to order quickly.

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  • Restaurants
  • Mexican
  • Lower West Side
  • price 1 of 4

What is it? A tiny Pilsen storefront devoted to the pig. 

Why go? The only decision you'll have to make when you visit this spot is how many pounds of pork you want to eat. Carnitas Uruapan's specialty is juicy pulled pork, served with corn tortillas, onions and salsa if you want to make your own tacos. The shop only stays open until 4pm on weeknights (5pm on weekends), so stop by early if you want to have authentic carnitas for dinner.

Don’t miss: Not leaving any part of the pig to waste, the limited menu also includes fresh, warm, delicious chicharrones (fried pork skin).

  • Restaurants
  • Pizza
  • Ashburn
  • price 1 of 4

What is it? A thin-crust-pizza paradise on the South Side. 

Why go? Believe it or not, most locals prefer thin crust to deep dish (which is predominately a tourist thing). And when it comes to authentic thin-crust Chicago ’za, the delightfully old-school Vito & Nick’s is ace. The spot has slung life-affirming pies in its cash-only Ashburn digs since 1932. (And no, they don’t do delivery.)

Don’t miss: Pair one of their expertly cooked cracker-thin tavern cut sausage pizzas with a pitcher of Old Style and consider yourself a real Chicagoan.

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  • Bars
  • Dive bars
  • Old Town
  • price 1 of 4

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.

  • Things to do
  • Literary events
  • Woodlawn

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 Osaka Japanese Garden.

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  • Shopping
  • Bookstores
  • Lower West Side
  • price 1 of 4

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.

  • Shopping
  • Antiques
  • Uptown
  • price 2 of 4

What is it? A store that's not for the faint of heart and is one hell of a conversation starter.

Why go? You never know what you'll find at this popular Andersonville antique store, which prides itself on stocking items that are "resurrected from the past." Taxidermy, diving helmets, military supplies and other interesting knick-knacks typically line the shelves.

Don’t miss: The anatomy items, medical stuff, skull bones (of all kinds) and skeletons.

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  • Restaurants
  • Ice cream parlors
  • Beverly
  • price 1 of 4

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. 

  • Sports and fitness
  • Baseball & softball
  • Wrigleyville
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What is it? Arguably the city’s most famous and beautiful place to see a ball game.  

Why go? Synonymous with the North Side for more than 100 years, the Friendly Confines has updated ever-so-slightly over the years. It eventually gave in and added lights in 1988; a jumbotron was erected in left field a few years back. But it’s the ivy that the lines the outfield walls, the manual scoreboard and general old-timey awesomeness that will keep the stands here filled whether the Cubbies are winning or losing. 

Don’t miss: For a true Wrigley Field experience, grab cheap(ish) tickets to the general admission bleachers section.  

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  • Sports and fitness
  • Stadiums
  • Armour Square

What is it? Home of the Chicago White Sox, formerly (and, to some, currently) known as Comiskey Park.  

Why go? Okay, so the South Side team doesn't command the rabid following of its neighbors to the north (although the whole city went nuts when it clinched the World Series in 2005). But the stadium is much more spacious than Wrigley, and it's almost always possible to walk up and purchase tickets.

Don’t miss: Sugar addicts, take note: A friggin’ three-pound banana split served in a novelty batting helmet is yours for the taking here.

Explore cinematic history at Doc Films
  • Movie theaters
  • Independent
  • Hyde Park

What is it? The University of Chicago's single-screen theater is the longest continuously running student film society in the country.

Why go? In the fall, winter and spring, this Hyde Park institution sheds light on some of the most obscure corners of film history, showcasing retrospectives of underappreciated directors, deep dives into highly specific movie genres and rarely-screened foreign films. Best of all, a ticket will only set you back $7.

Don't miss: Prefer to see something contemporary on the big screen? Stop by on Saturday nights, which are typically reserved for screenings of new and recent releases.

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  • Shopping
  • Music and entertainment
  • East Village
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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.

  • Movie theaters
  • Independent
  • Wrigleyville

What is it? Chicago's premiere arthouse theater. 

Why go? Aside from being one of the 50 most beautiful cinemas in the world, the Music Box's screens one of the best assortments of arthouse films, documentaries and foreign language pictures in the city. And if you prefer to turn your living room into a theater, Music Box Direct allows you to stream movies at home.

Don't miss: Performances on the theatre organ, which is played during weekend intermissions, monthly silent film screenings and other special presentations. 

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  • Restaurants
  • Seafood
  • South Deering
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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.

  • Bars
  • Lounges
  • Logan Square
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What is it? An expansive, bar-equipped arcade housed inside a former hardware store.

Why go? There are many arcade bars scattered throughout Chicago, but Logan Arcade boasts one of the largest (and best maintained) collection of games. You'll find classics like Ms. Pac-Man and Q*Bert alongside more modern machines like Mario Kart and a Jurassic Park shooter. Pinball wizards will flip over the selection of tables, including ones inspired by properties like Game of Thrones and Star Wars. Plus, you can sip a craft beer or cocktail between high-score attempts.

Don't miss: The Killer Queen cabinet, which allows two teams of five players to face off in a bee-themed battle that requires some intense cooperation to achieve victory.

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  • Things to do
  • Exhibitions
  • Loop
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What is it? The Chicago outpost of a chain of trippy "edutainment" destinations, packed with mind-bending photo-ops.

Why go? You'll be able to take a ton of cool Instagram photos at the Museum of Illusions, but you'll also have a chance to learn a thing or two along the way. Staff is present to explain the psychology and science behind each of the mind-bending displays.

Don't miss: The museum's infinity room, which surrounds guests with mirrors and shimmering lights.

  • Restaurants
  • Mexican
  • Archer Heights
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What is it? HQ for goat tacos in Archer Heights. 

Why go? This cozy birrieria has earned a cult following for its birria tatemada, which features goat that has been rubbed with an earthy mole and roasted. It's an utterly different approach from the stewing method used by nearly all of its Chicago competitors, and the result is something truly special. Zaragoza plates the meat with just a splash of consommé (which is vegetarian, another deviation from the norm); each juicy forkful is enhanced by a trace of burnt-end–like crust imparted by the roasted mole. 

Don’t miss: The thick handmade tortillas, made-to-order salsas and cinnamon-laced coffee are also lovely selections.

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  • Restaurants
  • Little Italy, UIC
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What is it? Al’s #1 Italian Beef has been keeping Chicagoans stuffed since 1938.  

Why go? While there are now several Al’s Beef locations around the city and suburbs, the original beef stand on Taylor Street is where you should visit this iconic Chicago restaurant. Here you can tangle with one of Chicago’s most classic foods, the Italian beef sandwich, in a cash-only neighborhood joint. You can order yours several ways, although dipped in juice with sweet peppers and giardiniera is the way to go.

Don’t miss: Eat yours utilizing the "Italian stance" (standing backed up with your feet spread apart and elbows over the counter) unless you want yours to end up all over your shirt.  

  • Bars
  • Breweries
  • Avondale

What is it? An Avondale brewery that focuses on German-style lagers. No IPAs here, but you'll find Pilsners, Kölsches and Schwarzbier.

Why go? Tons of Chicago breweries have outdoor patio spaces, but Metropolitan's riverside setup offers nicer views than most—and when the weather gets too cold, you can still soak in riverside vistas from floor-to-ceiling windows. 

Don't miss: Order a Krankshaft Kölsch, a smooth beer that has a touch of hops, some fruity notes and a crisp finish.

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  • Things to do

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 9pm to catch Art on theMART, the 25-story light projection show across the water.

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