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Graceland Cemetery
Photograph: Shutterstock/Carlos Yudica

The 59 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

Written by
Tim Lowery
,
Zach Long
,
Jay Gentile
&
Emma Krupp
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October 2021: The leaves are turning, there's a chill in the air and spooky decorations abound—it's officially fall in Chicago, folks. That means we've had to bid adieu to some of the summertime staples on this list, but rest assured that you'll still find plenty of ways to keep occupied as Chicago embraces a new season. This month, pay a visit to one of our favorite places to see fall foliage in the city and celebrate Halloween in Chicago at any number of blood-curdling haunted hauses scattered throughout the suburbs. Plus, check out a newly-opened exhibition on "The Office" and make the most of chilly weather at some of the coziest patios and outdoor dining spaces in Chicago (because winter will be here before you know it)!   

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. 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.

The best of the city in West Loop

  • 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, Mini Mott's delicious burgers, fried chicken from Cleo's Southern Cuisine and creative ice cream from Shawn Michelle's. And keep an eye out for events, concerts and artwork within the Market—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. Stop by this month to see "THINKING OF YOU. I MEAN ME. I MEAN YOU," a so-called "anti-retrospective" of conceptual artist Barbara Kruger's eye-catching work.

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? Garfield Park Conservatory's 10 acres of outdoor gardens—filled with scented blooms, ornamental trees, a glassy lily pond and other verdant attractions—are perfect for an afteroon amble through the flowers. Before you stop by to get your foliage fix, make sure to snag a reservation online.

Don't miss: The building’s haystack shape and walls of stratified stonework, creations of landscape architect Jens Jensen.

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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

  • 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.

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  • 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. Hop aboard the Chicago’s First Lady from its dock located along the beautiful Chicago Riverwalk for the socially-distanced 90-minute tour.

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

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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  • Things to do
  • Literary events
  • Uptown

What is it? Arguably Chicago's most iconic cemetery, home to the final resting places of famous denizens like Roger Ebert, Marshall Field and Daniel H. Burnham. 

Why go? Graceland offers a bunch of cool local history to explore any time of year, but its 119 acre expanses also happen to be home to more than 2,000 trees that erupt in splendid color once Chicago reaches peak fall foliage season. 

Don't miss: Before visiting, head to the cemetery's website and print out a free copy of a map to help you ID the graves of Graceland's most illustrious residents (and learn a bit more about the architects who designed their final resting places). 

  • 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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  • Things to do
  • Exhibitions
  • Magnificent Mile

What is it? An interactive pop-up dedicated to all things related to beloved NBC comedy The Office

Why go? You haven't really made liking The Office a part of your personality until you've posed at Michael Scott's desk, discovered Dwight's Jello-encased stapler hidden in a drawer or explored all the other nooks and crannies of this fairly true-to-show replica of Dunder Mifflin's Scranton branch. Once you've finished grabbing photo ops in the office, check out rooms dedicated to Pam and Jim's wedding and other key moments from the show. 

Don’t miss: Say what's on your mind at a pair of booths where you can set up your phone in a stand, take a seat in front of a window with blinds and record your own version of the show's documentary-style confessionals. 

  • Bars
  • Dive bars
  • River West/West Town
  • price 1 of 4

What is it? A tucked-away, homey music mecca on an industrial stretch of the city.

Why go? After 17 months of virtual concerts and programming, the Hideout has finally reopened its doors to the public for in-person shows on the patio. Remember to bring your vaccination card (or a photo of it; either way, you'll need to be fully vaccinated to enter) and buy your tickets ahead of visiting. 

Don’t miss: The return of Veggie Bingo (every Wednesday from 6 to 8pm) and the debut of the new weekly stand-up comedy show Yard Party.

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  • Things to do

What is it? Creepy haunted experiences full of zombies, ghosts, killer clowns and other scream-inducing horrors.  

Why go? You'll have to schlepp it to the suburbs to find the Chicago area's best haunted houses, but these seasonal attractions are back and better than ever after mostly taking the year off in 2020. 

Don’t miss: Basement of the Dead, a top-rated, heart-palpitatingly scary haunted house operating out of a 120-year-old building in downtown Aurora. 

 

  • Restaurants

What is it? Who says we can't push patio season just a little longer? These extra-cozy spots make it easy to have a drink or meal in the open air when temps start to drop (though you might want to bring a sweater).   

Why go? Because of last year's push for expanded outdoor dining, tons of Chicago bars and restaurants have outfitted their patios with heaters, firepits and other nifty features that will help you stay warm while imbibing and dining alfresco. 

Don’t miss: Gorge on tacos while huddled around a firepit at Pilsen Yards, a music-centric joint tht opened in the former Monnie Burke's space earlier this year. 

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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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  • Things to do
  • Festivals
  • River West/West Town

What is it? An annual pop-up that brings a pumpkin patch, corn maze and more fall attractions to a two-acre lot in Goose Island.

Why go? It might be more legit to hop in a car and pluck a pumpkin straight from the farm-grown vine, but you certainly won't find any other pumpkin patches within city limits; plus, it helps that you can score drinks from three bars scattered throughout the premises.

Don’t miss: A general admission ticket nets you access to the pop-up, but you can also opt for add-ons that let you take home a pumpkin, grab a drink or go axe-throwing.

  • 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 kind 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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  • Art
  • Sculpture
  • Suburbs

What is it? A large-scale outdoor exhibit titled "Human+Nature," with five works from the South African artist Daniel Popper spread across the Morton Arboretum's sprawling grounds in suburban Lisle.

Why go? The towering works—all 15 to 26 feet in height and made of glass-reinforced concrete, wood, fiberglass and steel—depict human figures interacting with their natural surroundings, creating some awe-inspiring sights tucked into the abundant greenery of the Arboretum.

Don't miss: The gentle-looking "UMI" sculpture lends a maternal feel to a glen of magnolia trees on the park's east side. 

  • Shopping
  • Markets and fairs
  • West Loop

What is it? When it was established in the late 19th century, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. Nowadays, the market functions as a hub for vendors to sell handmade crafts, resale goods, clothes and top-notch street food. 

Why go? You never know what treasures you might find, from candy pink cowboy hats to some of the city's most delicious tacos.  

Don't miss: It's free to enter the market, but bring a wallet stuffed with cash—many of the vendors don't accept cards. 

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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 and kayak rental companies also have launch points along the Riverwalk, if you prefer to get out on the water.

Don't miss: Enhance your walk along the water with a ginger cardamom iced chai from Chiya Chai Café, an outpost of the Logan Square cafe that's located in the Riverwalk's Community Marketplace.

  • Art
  • Architecture
  • Loop

What is it? A career retrospective of the German-born, Chicago-based architect Helmut Jahn—who designed local structures like the James R. Thompson Center and Terminal 1 (including its popular neon-lit walkway) at O'Hare International Airport—at the Chicago Architecture Center.

Why go? Jahn died earlier this year after being struck by a car while riding his bicycle in suburban Chicago, so the exhibit functions a poignant tribute to his architectural influence in Chicago and worldwide—especially as the Thompson Center downtown faces an ongoing preservation battle.

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

What is it? You have to listen 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 4 am Thursdays and Fridays and 5 am 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 van der Rohe 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 van der Rohe's 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
  • Old Town

What is it? A high-tech experience inside the Germania Club Building that brings Vincent Van Gogh's paniting to life with the help of 50 digital projectors.

Why go? The tickets to "Immersive Van Gogh" aren't cheap, but you've likely never seen anything quite like this exhibit, which animates some of Van Gogh's most famous works and sets them to a booming sountrack. The 35-minute presentation is filled with impressive moments—and plenty of great photo ops.

Don't miss: Stop by the "Immersive Van Gogh" gift shop on your way out to pick up shirts, masks and more swag covered in colorful brushstrokes.

  • 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 to view the furniture collection available for sale, where you'll find items from iconic designers like Vladimir Kagan, Jens Risom and Eero Saarinen.  

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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? Sure, you could pay for a ticket to a zoo, but more than 1,000 critters are waiting for you to visit them, free of charge (just make a reservation), 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. 

  • 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. 

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

What is it? A 700-ton German submarine that was captured during World War II and transferred to the Museum of Science and Industry in 1954.

Why go? The U-505 is one of only four surviving German U-boats, housed in a gigantic 35,000-square-foot enclosure. Equally as impressive as the giant hardware are the smaller artifacts that were recovered from within the ship, including a code-breaking Enigma machine, cigarettes and German phonograph records.

Don't miss: See even more vintage vehicles in the MSI's Transportation Gallery, including a Boeing 727 and a steam locomotive. There's also a traveling exhibition devoted to Marvel super heroes on display.

  • Restaurants
  • Chinese
  • Armour Square

What is it? The revival of a longrunning Chinatown institution, overseen by Kenny Yang of Strings Ramen Shops.

Why go?: With decor and neon accents inspired by he streets and markets of 1950s Hong Kong, Ken Kee is like two restaurants in one. Order crab rangoon, assorted congee and beef brisket casserole from the all-day menu, or opt for the Noodle Cart offerings (served from a dedicated kitchen). You can customize your noodle bowl to your liking, picking the broth, the noodles and all of the delicious toppings from a long list of options.

Don't miss: The Noodle Cart is likely to be the main attraction, but the deep menu of classic Hong Kong and American-Chinese dishes is worth your time, too. And there's nothing stopping you from ordering from both.

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  • Movie theaters
  • Independent
  • Wrigleyville

What is it? Chicago's premiere arthouse theater, which is currently hosting indoor screenings and offering streaming options for those who are staying home.

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're not ready to venture out to see a movie yet, Music Box Direct allows you to stream movies at home and help keep the theater afloat.

Don't miss: Missing the Music Box's made-with-real-butter popcorn? You can order it to-go, accompanied by boxed candies and beverages.

  • 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 Visitor Center 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.

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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  • 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.

  • Travel
  • Transport & Travel

What is it? These jet-black e-bikes have joined the Divvy fleet, allowing riders to go up to 15 miles per hour with the help of a small electric motor.

Why try it? Let's face it: the original bright blue Divvy bikes are heavy and cumbersome. These new e-bikes (which you'll find at stations throughout the city) make it easier to see more of the city atop a shared ride. The pedal-assist system adds some additional power everytime you move your legs, allowing you to get to your destination faster—and possibly without breaking a sweat.

Don't miss: Divvy e-bikes come with an attached lock, meaning that you can end your ride by locking it to a bike rake or sign post, though you may incur an extra fee. You can also place them in any Divvy dock.

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  • 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.

  • 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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  • 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 the lockdown. You can say hi to them in the Polar Play Zone exhibit.

  • Bars
  • Breweries
  • Lincoln Square

What is it? The far North Side warehouse where one of the city's largest breweries produces the majority of its beer.

Why go? Half Acre Balmoral's expansive parking lot patio offers room to enjoy signature brews like Daisy Cutter and Tome in the open air. Just make a reservation, show up with some friends and sip beers in the in the open air (or in heated tents, if temps are too low). Plus, a new menu of bar food is available for hungry drinkers.

Don’t miss: There are beers on tap here that are exclusive to this location, so be on the lookout. 

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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 popular 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.

  • 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). 

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  • Sports and fitness
  • Kayaking & canoeing
  • River North
  • price 2 of 4

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.

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

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

Why go? Guests can now book reservations inside the airy Lincoln Park restaurant, where an army of staff plate your dishes and re-fold your napkin. But if you'd rather get takeout, you can also purchase Alinea meals to go. The three-course meals start at $35 and are accompanied by reheating instructions—not bad for fine dining cuisine that's usually a triple figure investment.

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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  • Shopping
  • Toys and games
  • Sheffield & DePaul
  • price 2 of 4

What is it? A designer toy store and gallery in Lincoln Park that's filled with cute tchotchkes to display on your desk.

Why go? Rotofugi offers one of the most extensive selections of contemporary toys (for kids and adult collectors) in all of Chicago, whether you're looking for blind box vinyl figures, Japanese capsule toys or fancy sculptures.

Don't miss: The in-house art gallery, which hosts free shows for visitors to peruse. 

  • 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
  • Suburbs

What is it? A bar in Blue Island, Illinois (just across Chicago city limits) that has created its own drive-in theater.

Why go? You can show up for a free screening every Friday, Saturday and Sunday—parking spots are first come, first served. Food and drinks are available for purchase while you're enjoying the movie.

Don't miss: Every weekend's lineup of screenings has a theme, from kung-fu flicks to rock 'n roll movies. Check out the schedule to see all the coming attractions.

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  • 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.

  • 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 curbside pickup and in-store browsing.

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 that 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. 

  • Shopping
  • Music and entertainment
  • East Village
  • price 1 of 4

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.

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  • Restaurants
  • Seafood
  • South Deering
  • price 1 of 4

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.

  • Restaurants
  • Bakeries
  • Logan Square
  • price 1 of 4

What is it? A small pie and biscuit restaurant in Logan Square with an expansive backyard patio.

Why go? The various pies at Bang Bang Pie & Biscuits are delicious wherever you decide to eat them, but they somehow taste even better when you dig in on the rustic patio behind the shop (currently open on Thursday through Saturday). Snag a slice of key lime or peanut butter and soak up some sun between bites.

Don't miss: It's easy to get distracted by all the sweet treats, but Bang Bang's savory options are just as delicious. We love the fluffy biscuit topped with vegetarian gravy and an egg.

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  • Things to do
  • Exhibitions
  • Loop
  • price 2 of 4

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
  • price 1 of 4

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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  • Things to do
  • South Shore

What is it? The 18-mile-long path is the best way to soak up those lakefront views. 

Why go? Stretching from Hollywood Avenue on the north all the way to 71st Street to the south, the Lakefront Trail provides a path along the coast of Lake Michigan that connects tons of neighborhoods. Once you're on the trail, expect bicyclists zooming by, joggers pounding the pavement and pedestrians out for a leisurely stroll. 

Don’t miss: Whatever mode of transportation your choose, don't forget to stop for a moment and take in the amazing views of the Chicago skyline.

  • 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. 

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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  • Restaurants
  • Little Italy, UIC
  • price 1 of 4

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.  

  • Restaurants
  • Contemporary American
  • West Loop
  • price 2 of 4

What is it? Where fancy-burger fanatics flock in the West Loop. 

Why go? There's a good reason why you'll never be able to show up at Au Cheval and immediately be seated: The West Loop restaurant's signature cheeseburger has achieved a near-legendary status as a must-eat Chicago dish. Served with a knife protruding from the top of its puffy bun, the "single" version comes with two beef patties, while the "double" includes three. Au Cheval doesn't take reservations, so plan on finding a nearby spot to grab a drink while you wait to indulge.

Don’t miss: The matzo ball soup, stocked with roasted carrots and cippolini onions, is damn delicious too. 

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  • 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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