Best things to do in Chicago that locals and tourists will love

Discover the best things to do in Chicago, from iconic meals and views to cultural musts and late-night shenanigans
By Jay Gentile, Zach Long, Tim Lowery and Morgan Olsen |
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No matter where your interests lie, you can always find something to get excited about in this no-nonsense Midwestern metropolis. Looking for culture? Spend a day exploring Chicago museums or stay out late and catch killer concerts in Chicago. 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. (There are 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.

Find out more about how Time Out selects the very best things to do all over the world.

47 best things to do in Chicago

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Photograph: Jaclyn Rivas
Attractions, Parks and gardens

See concerts and public art in Millennium Park

icon-location-pin 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. In the summer, the area is typically teeming with folks catching free concerts and movie screenings on the lawn at the Frank Gehry-designed Jay Pritzker Pavilion. (Psst: It's usually BYOB). When it gets cold, you'll find skaters sliding across the ice at the McCormick Tribune Ice Rink. 

Don’t miss: Crown Fountain, an interactive installation featuring two 50-foot-tall LED video structures separated by a reflecting pool. (Feel free to get wet and splash around if the mood strikes.) 

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Things to do

Hop aboard Chicago’s First Lady for an architecture tour

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 50-plus downtown buildings. Hop aboard the Chicago’s First Lady from its boat docking station located along the beautiful Chicago Riverwalk for the 90-minute tour.

Don’t miss: Of course there's a full-service cash bar inside. You can also bring your own (individually wrapped) food.

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Things to do

Get high at the Willis Tower Skydeck

icon-location-pin Loop

What is it? Where to see the city from 1,353 feet above the streets.

Why go? The observatory's Ledge attraction places visitors in a glass box that juts out over the side of the building, allowing for some pretty epic selfies and views. How epic? Views from the 103rd floor are expansive, allowing guests to see up to four states and 50 miles out. Damn.  

Don’t miss: Want to beat the crowds? Experience the skyline at night. It's open until 8pm October through February and until 10pm March through September.

 

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Theater

See a stellar play at Steppenwolf Theatre Company

icon-location-pin Lincoln Park

What is it? What people think of when they hear "Chicago theater." 

Why go? Founded in the basement of a Highland Park church, the Steppenwolf Theatre Company has grown to embody the hardworking ethos of the Chicago theater community. It was home to maybe the world’s most famous acting ensemble (Gary Sinise, John Mahoney, Laurie Metcalf, Martha Plimpton and William Petersen). And these days, the company occupies an expansive venue with three stages in Lincoln Park, where you can see groundbreaking shows nearly every night of the week. 

Don’t miss: The chance to see a big name onstage. In recent years, Steppenwolf has become a place where established actors (such as Rainn Wilson, Michael Cera and Michael Shannon) come to show off their chops on stage. 

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Art of Medieval and Renaissance Europe
Photograph: Courtesy The Art Institute of Chicago
Museums, Art and design

Eye masterpieces at the Art Institute of Chicago

icon-location-pin Grant Park

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. But did you know that the museum also houses a Medieval armory? Located just past the Renaissance Art on the second floor, you'll find an impressive collection of swords, crossbows and some gorgeous suits of armor.

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 kid.

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Photograph: Martha Williams
Bars, Cocktail bars

Tap your toes to late-night jazz at the Green Mill

icon-location-pin Uptown

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. The music typically goes until 1am (later on the weekends) and the lineup of performers includes B-3 organ players, jazz vocalists and classic big bands. Order a cocktail and settle in for a late, throwback night. 

Don’t miss: Taking a picture under the glittering marquee. 

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Photograph: Amy Cavanaugh
Restaurants, Hot dogs

Fill up on Chicago-style cuisine at Hot "G" Dog

icon-location-pin Uptown

What is it? Where crazy-creative spins on the the hot dog reign supreme. 

Why go? Beloved Chicago hot dog stand Hot Doug's shut down years ago, but owner Doug Sohn left a worthy heir to his encased meat throne. Located in Uptown, Hot "G" Dog is run by a group of cooks who formerly prepared the orders at Hot Dougs, serving a menu similar to the one offered at the old Avondale stand. You'll find great Chicago dogs, sausages made with alligator or goat meat and duck fat fries on the weekends. Arrive with an appetite.

Don’t miss: The duck sausage, with medallions of foie gras, truffle aioli and fleur de sel.  

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Photograph: Matthew Gilson
Restaurants, Contemporary American

Have a mesmerizing meal at Alinea

icon-location-pin Lincoln Park

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

Why go? In 2016, Lincoln Park stalwart Alinea underwent a massive renovation, swapping its dark, sexy interior for an airy, timeless space. Though Alinea’s tasting menus will set you back $190 to $395 a person, every course is a theatrical masterpiece delivered with flawless service: Prepare for lots of dry ice, exotic fruits and playful servingware.

Don’t miss: One of Achatz’s signature helium taffy balloons, which fill the dining room with smiles and high-pitched laughter.

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The Second City etc.
Photograph: Todd Rosenberg
Comedy, Comedy clubs

Double over laughing at the Second City

icon-location-pin Lincoln Park

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 institutions most talented performers in a series of loosely-connected, topical comedy sketches. 

Don’t miss: Once the show is over, stick around for the encore, where the cast tests out new sketches and get to show off their improv talents.

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Photograph: Neal O'Bryan
Sports and fitness, Baseball & softball

Root, root, root for the home team at Wrigley Field

icon-location-pin Wrigleyville

What is it? Arguably the 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: What’s a game without a cold brew and a hot dog? Be like a real Chicagoan, though, and skip the ketchup on the latter.

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Photograph: Ron Vesely
Sports and fitness, Stadiums

Catch a foul ball at Guaranteed Rate Field

icon-location-pin Armour Square

What is it? Home of the Chicago White Sox (and a favorite of local hero Chance the Rapper).  

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.

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Photograph: Courtesy Carnitas Uruapan
Restaurants, Mexican

Pig out on pork tacos at Carnitas Uruapan

icon-location-pin Lower West Side

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 5pm on weeknights (6pm 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.

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Attractions, Parks and gardens

Find serenity at the Garfield Park Conservatory

icon-location-pin East Garfield Park

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

Why go? Even when the weather outside is crummy, it's always warm inside the Garfield Park Conservatory. Admission is always free (though you're welcome to make a donation). Make sure you take a moment to walk around the tropical paradise of the Palm House, the conservatory's largest room, and take a peek inside the Fern Room, which attempts to recreate the vegetation in Illinois millions of years ago.

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

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Photograph: Martha Williams
Bars, Cocktail bars

Pretend you’re in the tropics at Lost Lake

icon-location-pin Avondale

What is it? A boozy island vacation in the heart of Logan Square. 

Why go? Escape to a place where the walls are plastered in palm leaves, the bartenders are clad in Hawaiian shirts and drinks are served with a barrage of colorful straws and garnishes. Helmed by bartender Paul McGee, Lost Lake makes a small storefront in Logan Square feel like a much-needed getaway, complete with a shifting menu of tiki drinks that range from strong, rum-forward concoctions to sippable, fruit juice-infused cocktails.

Don’t miss: Sharable large-format cocktails that everyone can enjoy.

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Photograph: Martha Williams
Restaurants, Pizza

Devour thin crust 'za at Vito and Nick’s Pizzeria

icon-location-pin Ashburn

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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Photograph: Martha Williams
Music, Rock and indie

Catch rising bands at the Empty Bottle

icon-location-pin Ukrainian Village

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: The free shows on Monday nights.  

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Half Acre
Photograph: Courtesy Half Acre
Bars, Breweries

Sip suds at Half Acre Brewery Balmoral

icon-location-pin Lincoln Square

What is it? An inside look into the creation of some of the city's most buzzed-about brews. 

Why go? As fun as it is to drink Half Acre's Daisy Cutter Pale Ale or its Pony Pilsner, it's even more fun to see how the beer gets into the can. The brewery's Balmoral facility in Lincoln Square hosts tours every Sunday at 11am. Just show up with $10 in cash and you'll get a behind-the-scenes look at Half Acre's process, as well as three samples and a pint glass to take home.

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

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Museums, Science and technology

Hang out with a mummy at the Field Museum

icon-location-pin Museum Campus

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.

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Queen!
Photograph: Erik Commer
Bars, Lounges

Get down to house music at Smart Bar

icon-location-pin Wrigleyville

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 weekly Queen dance party every Sunday. 

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Photograph: Marc Monaghan for the John D. and Catherine T. MacArthur Foundation
Theater, Interactive

Watch 30 plays in 60 minutes at the Neo-Futurarium

icon-location-pin Uptown

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: Tickets are $9 plus the roll of a six-sided die (really), so bring a lucky pal. 

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Photograph: Erica Gannett
Bars, Dive bars

Have a PBR at Rainbo Club

icon-location-pin Ukrainian Village

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.

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Attractions, Historic buildings and sites

Marvel at Frank Lloyd Wright’s architecture at the Robie House

icon-location-pin Hyde Park

What is it? What 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. 

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Lincoln Park Zoo lemur
Photograph: Chris Bijalba/Lincoln Park Zoo.
Things to do

See animals (for free!) at Lincoln Park Zoo

icon-location-pin 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, 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. 

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Photograph: Marina Makropoulos
Bars

Bar hop in Boystown

What is it? The heart of the city’s LGBTQ community is also prime pub-crawl territory.

Why go? Nestled in the Lakeview neighborhood, Boystown is the city’s most popular queer-culture destination. Take in all of the action but hitting a few watering holes, including the ever-popular, expansive and mingle-friendly Sidetrack, drag-show bar Kit Kat Lounge and refined cocktail bar Elixir. 

Don’t miss: The rainbow-colored pylons scattered along Halsted Street.

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Photograph: Adam Alexander/courtesy of The Trust for Public Land
Attractions, Parks and gardens

Travel across an elevated trail on the 606

icon-location-pin 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: Take a spin on your Divvy, go for a jog or simply use it to walk between a bar and a nearby restaurant during a warm night out.

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Photograph: Max Herman
Movie theaters, Independent

Become a cineaste at the Music Box Theatre

icon-location-pin Wrigleyville

What is it? Chicago’s gorgeous two-screen movie palace has been going strong since 1929.

Why go? For movie lovers who don't care for traditional Hollywood blockbusters, there's no better mecca this cinema that shows the latest art-house films and documentaries. Its design is stunningly ornamental and old school. And the retro fun doesn’t stop there: The concession stand even tops its popcorn with real butter.

Don’t miss:  Big-deal director Q&As, rowdy midnight screenings of cult classics and rare 70-millimeter presentations.

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Paul McCartney brings his Out There tour to the United Center, July 9, 2014.
Photograph: cousindaniel.com
Things to do, Event spaces

Cheer on “da Bulls” at the United Center

icon-location-pin United Center

What is it? Home to pro basketball and hockey, as well as big-ticket pop acts. 

Why go? You can't see Michael Jordan play at the United Center anymore (though you can get a picture in front of his statue in the venue's public atrium), but this West Side arena still hosts plenty of stars. During basketball and hockey season, the venue serves as home turf for the Bulls and the Blackhawks—two of the city's biggest pro sports teams. It's also a destination for major pop and rock concerts, including acts like U2, Drake and Madonna.

Don’t miss: The arena has partnered with local restaurants like Big Star, Leghorn Chicken and Lillie’s Q to provide dishes and drinks that handily outclass typical stadium fare.   

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Restaurants, Ice cream parlors

Get your licks in at the Original Rainbow Cone

icon-location-pin Beverly

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 sherbert ice cream.

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

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Photograph: Brendan Lekan
Restaurants, Seafood

Sample smoked seafood at Calumet Fisheries

icon-location-pin South Deering

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.

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Restaurants, Mexican

Get a taste for goat at Birrieria Zaragoza

icon-location-pin Archer Heights

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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Photograph: Martha Williams
Bars, Dive bars

Booze at Old Town Ale House

icon-location-pin Old Town

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.

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Photograph: Jaclyn Rivas
Restaurants, American

Fill your gut at Al’s #1 Italian Beef

icon-location-pin Little Italy, UIC

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.  

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Photograph: Kimberly Vardeman/Flickr
Restaurants, American

Sip cocktails atop 875 N Michigan Ave

icon-location-pin Streeterville

What is it? The Signature Lounge at the 96th boasts one of the best all-expansive, panoramic views of Chicago.

Why go? Instead of paying the $20 to get into the 94th-floor Hancock Observatory, take the bullet-fast elevator up to this 96th-floor bar in the sky and drop that cash on a stiff drink. Perched high over the city, long-popular bar located at the old John Hancock Center (which is now called 875 N Michigan Ave) has huge floor-to-ceilings windows to take it all in.

Don’t miss: The panoramic, vertigo-inducing views of the city never get old.

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Woolly Mammoth Antiques and Oddities Shop in Andersonville.
Photograph: Jamie DiVecchio Ramsay
Shopping, Antiques

Find something strange at Woolly Mammoth Antiques & Oddities

icon-location-pin Uptown

What is it? A store that's not for the faint of heart but 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 stuffs, skull bones (of all kinds) and skeletons. 

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Photograph: Marina Makropoulos
Restaurants, Chinese

Have dim sum at Phoenix Restaurant

icon-location-pin Armour Square

What is it? The Chinatown destination hosts one of the most authentic dim sum experiences in Chicago. 

Why go? During the week, Phoenix Restaurant serves Beijing Duck, Hong Kong Steak, seafood and more delicious Americanized Chinese dishes. On the weekends, though, it's all about dim sum, as carts laden with steamed barbecue pork buns, Malay steamed cake and egg tarts roam the room—just grab what you want and the servers will tally the bill for you.

Don’t miss: Save room for interesting options like tender baby octopus with a slight curry flavor and crispy eggplant stuffed with steamed squid.

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Photograph: Anthony Soave
Comedy, Comedy clubs

Chuckle to long-form improv at iO Theater

icon-location-pin River North

What is it? The house that improv legend Del Close and founding partner Charna Halpern built.

Why go? While most people think of Second City when they think of comedy in Chicago, iO Chicago (formerly the ImprovOlympic) has been performing more theatrical, long-form improv with highly developed characters and stories since 1981. With legions of famous alumni including Tina Fey and Amy Poehler, these days a newly expanded iO features four theaters, two bars, a beer garden, kitchen, and a training center.

Don’t miss: The show Whirled News Tonight, when the cast acts out news articles that the audience clips to a bulletin board.

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Photograph: Courtesy of Christina Cou
Things to do, Literary events

Go back at the Historic Pullman Foundation Visitor Center

icon-location-pin Pullman

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. 

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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Photograph: Kevin J. Miyazaki
Restaurants, Contemporary American

Scarf a tasty burger at Au Cheval

icon-location-pin West Loop

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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Photograph: Jaclyn Rivas
Bars, Dive bars

Dance the night away at the Hideout

icon-location-pin River West/West Town

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

Why go? Little more than an Old Style sign to denote its existence, but inside this former 1881 balloon-frame house, you’ll find a watering hole that’s truly unique. The Hideout feels like your cool uncle’s basement populated with a hip crowd checking out whatever’s going down on the twinkling lights-decorated stage.

Don’t miss: Though the venue mostly books live bands, the late-night weekend dance parties are fun, sweaty affairs.

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Chicago Lakefront Trail
Photograph: Alanscottwalker
Things to do

Bike (or walk) along the Lakefront Trail

icon-location-pin 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 and take in the amazing views of the Chicago skyline.

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Photograph: Clayton Hauck
Restaurants, Soul and southern American

Chill on the outdoor patio at Parson’s Chicken & Fish

icon-location-pin Logan Square

What is it? A fried chicken haven with a destination-worthy backyard patio.

Why go? Grab a spot beneath the red and white striped umbrellas at one of the city’s most popular summer patios, where you can dig into a mouth-pleasing assemblage of fried (or grilled) chicken paired with iconic summer cocktails like the Negroni slushy. Despite recent renovations, the patio still retains its Austin-esque hipster charm. You can also dine inside or chat up randoms at the cozy indoor bar when the weather isn’t cooperating.

Don’t miss: Parson’s now serve its own suds, Parson’s Beer, brewed in collaboration with nearby Revolution Brewing.

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Skylanding
Photograph: Neal O'Bryan
Things to do, Literary events

See Yoko Ono’s installation in Jackson Park

icon-location-pin 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, Music and entertainment

Dig through vinyl at Dusty Groove

icon-location-pin East Village

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. It's the kind of place you'd have to hit if you were soundtracking a Tarantino film. If the selection makes you feel overwhelmed, don't hesitate to strike up a conversation with the friendly staff—they can point you toward your new favorite record. 

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

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Photograph: Courtesy the Beer Temple
Shopping, Liquor stores

Drink all the brews at the Beer Temple

icon-location-pin Avondale

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, which has gained a reputation for stocking the most sought-after releases from local and out-of-state brewers. Browse the chalkboard menu at the bar, order in some food from a nearby restaurant or sit down in one of the back rooms and settle into a board game.

Don’t miss: The bar also hosts a bottle shop, where you can browse six-packs, bombers and more booze to take home with you.

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Photograph: Max Herman
Music, Folk, country and blues

Hear live blues at Kingston Mines

icon-location-pin Sheffield & DePaul

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 nightly and 5 am on Saturdays. Whether you’re hangin’ 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.

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Things to do

Enjoy the sun and sand on Montrose Beach

icon-location-pin Uptown

What is it? Proof that life's a beach, even in Chicago. 

Why go? The closer you get to the Loop, the more crowded Chicago's beaches can become. Which is why it sometimes pays to travel a little farther to lay out on the sand. The crowds at Montrose Beach in Uptown are usually a bit more manageable, and the amenities are comparable to the city's most popular stretches of sand. 

Don’t miss: Sick of lazing on the sand? Motrose also offers  volleyball courts and kayak rentals. 

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Photograph: Neseman Creative
Nightlife

Have your mind blown at the Chicago Magic Lounge

icon-location-pin Uptown

What is it? A love letter to all things magic.

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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