The 18 All-Time Greatest Things to Do in Chicago

There are countless cool things to see, eat, and do in Chicago right now.

Photo by Jaclyn Rivas for Thrillist
Photo by Jaclyn Rivas for Thrillist
All Time Greats is the ultimate city bucket list. Whether you’re a local or a visitor, consider this the essential guide to getting the most out of Chicago. Looking for events happening this weekend? Check out our Chicago weekend guide.

At the risk of sounding hyperbolic, Chicago is the rare city that really does have it all. It has all seasons, from the sweltering humidity of summer to the polar vortices of winter. It has towering skyscrapers and cozy brownstones. It has tasting menus and frills-free street food aplenty. It’s got world-class museums, Michelin stars, Taylor Swift-worthy stadiums, and the most iconic comedy club in the nation. And it has a whopping 77 neighborhoods (with a 78th on the way!), sprawled across 234 square miles of prime lakefront in northeast Illinois.

The third largest city in the country, a broad-shouldered behemoth that likes to compare itself to New York and flaunt itself as the metropolitan epicenter of the Midwest, Chicago undoubtedly boasts a lot to do, see, eat, and drink. Foodies could spend weeks eating their way through the West Loop alone, or hopping from rooftop bar to rooftop bar in the Loop and River North. Culture connoisseurs have a plethora of museums and live entertainment to choose from, year round. And tours here, whether a self-guided stroll on an urban trail or a cruise through an architectural Grand Canyon, offer a wealth of sights and experiences. In this ever-evolving town, it’s impossible to see all that Chicago has to offer, but this bucket list should offer a great introductory taste of what makes this city so great. Here are 18 of the all-time greatest things to do in Chicago.

 Pequod’s Pizza
Pequod’s Pizza | Photo by Jaclyn Rivas for Thrillist

Where to eat and drink in Chicago

Fulton Market
The Fulton Market portion of the West Loop has really calcified as the nexus of Chicago’s famed food scene. Here, throughout a warehouse district formerly dominated by wholesale meatpackers, some of the city’s most acclaimed chefs and restaurants reign. Nowadays, anybody who’s anybody has a restaurant (or several) here, from Grant Achatz to Boka Restaurant Group. But just as One Off Hospitality Group pioneered the greater West Loop with Blackbird and avec, they did the same with The Publican. Open since 2008, in a vast and lofty dining room, this meaty wonderland is an apt homage to Fulton Market’s meatpacking heyday. Plus oysters. Plus beer. Plus farm-fresh vegetables that change near-daily. The clamorous restaurant feels like dining in a European beer hall, with an open kitchen churning out burly portions of country ribs, pork rinds, and roast chicken with golden frites. And it’s all as spirited and lively as it was on day one. For something more casual, head next door to Publican Quality Meats, a quasi-market, cafe, and butcher shop, where Chicago’s most acclaimed butcher, Rob Levitt, slings charcuterie plates and sandwiches.

Rooftop bars

Loop
As the birthplace of the skyscraper, it’s no wonder that Chicago takes great pride in its sky-high rooftop bar scene. Whether it’s the second floor or the 26th, rooftop bars come in all shapes, sizes, and styles, and although some are located in outlying neighborhoods (e.g. The Robey Chicago hotel in Wicker Park and The J. Parker in Lincoln Park), most are scattered around the downtown core. One of the most famed is Cindy’s, the elegant open-air terrace atop the Chicago Athletic Association hotel, where the high-end drinks are just as stunning as the views of Millennium Park and Lake Michigan. LH Rooftop is another must, for its unparalleled views of the Chicago River from the 22nd floor of the LondonHouse Hotel. Elsewhere, there’s Latin American-themed Boleo atop the Kimpton Gray Hotel in the Financial District, Cerise on the 26th floor of the Virgin Hotels Chicago, and Château Carbide, a lush Champagne-soaked oasis atop the Art Deco Pendry Chicago.

West Loop
Burgers are a dime a dozen in this beef-loving city. But few can hold a candle to the legendary double cheeseburger at Au Cheval. Ever since the neo-diner opened in the heart of the West Loop in 2012, it’s commanded hours-long wait times to snag seats. And that’s almost entirely due to said burger, whose popularity has regularly earned it praise as among the best in the country. Whether or not you believe the hype, or bemoan it, it’s a burger that’s well worth the extra effort to attain it. For something so seemingly simple, a pair of griddled patties topped with cheese and bacon on a buttery toasted bun, it’s oddly perfect. So much so that Au Cheval spawned a fast-casual spin-off brand, Small Cheval, with locations around the city.

Deep-dish at Pequod’s Pizza

Lincoln Park
One touristy taboo you do not want to do is waste your time in line for a downtown “icon” like Pizzeria Uno or Gino’s East. More like pizza theme parks, serving dense casserole-like pies layered with burger-thick sausage patties, you are far better served ticking your deep-dish box elsewhere. Like Pequod’s Pizza in Lincoln Park. Removed from the touristy downtown fray, this is the kind of dark and cavernous haunt that legitimizes the craft, and shows that deep-dish can be done right. After the original location opened in Morton Grove in 1970, the brand quickly earned acclaim for its caramelized crust, markedly different from the typically bready norm, achieved by lining the outer layer of the dough with mozzarella before baking. The Lincoln Park mainstay emerged in 1992, forever shifting the landscape of deep-dish in city limits, and offering a spin on stereotypical Chicago-style pizza that locals could actually get behind.

Molecular cocktails at The Aviary

Fulton Market
An evergreen addition on our list of best bars in Chicago, The Aviary is singular. That’s thanks to Grant Achatz, the most famed chef in the city, and the mind behind Chicago’s only restaurant with three Michelin stars, Alinea. For his first foray into mixology, he applies the same cheffy approach to cocktails, employing a laboratory-like bar where bartenders are trained like chefs and the drinks are so whimsical and molecular—served in wonky stemware like balloons and spheres, wafting in smoke like some sort of bougie potion—that they barely look potable. Cocktails here are ever-changing, and available in “tasting menus,” because Achatz.

River North
Somehow, Chicago’s foremost tiki bar has only gotten more and more popular—and more and more innovative—over the years since its clandestine debut in 2013. Hidden down a tiki torch-lined alley in River North, Three Dots and a Dash is a game-changing speakeasy-style tiki temple, with over-the-top libations, immersive ambiance, and an entry hallway lined with skulls that makes you feel like you’re queueing up for Pirates of the Caribbean. The bar boomed with popularity when it opened, riding the national tiki renaissance wave, but it’s only gotten better with age. That’s largely thanks to the guidance of beverage director Kevin Beary, who oversees an enthralling menu of lustrous drinks and punch bowls. Go with a group to order the Shotstapus, a series of rum-based shots served in tentacles. Try and snag a stool at The Bamboo Room, basically a boutique tiki bar within a tiki bar, where Beary serves more meticulous and elevated drinks rooted in rum and rhum agricoles.

Ukrainian Village
Come for Chicago’s most rightfully famed breakfast sandwich, and then come back for a dinner degustation. That’s the power move at Kasama, a newly Michelin-minted Filipino affair from husband-wife team Tim Flores and Genie Kwon, who offer casual cafe fare by day before pivoting to Chicago’s only Filipino tasting menu at night. No matter when or how you visit, you’re in for a treat, be it the egg and cheese breakfast sandwich with longanisa sausage, an ube and huckleberry Basque cake, or a 13-course spree of ever-changing modern Filipino fare.

Millennium Park
Millennium Park | Photo by Jaclyn Rivas for Thrillist

Arts and live entertainment in Chicago

Loop
One museum worth playing hooky for, the colossal Art Institute of Chicago is not only one of the best museums in the city, but among the best in the nation—and one of the best art museums on Earth. Clocking in at 562,000 square feet in downtown’s Grant Park, with upwards of 300 galleries and 300,000 pieces of art, the labyrinthine museum boasts everything from Chinese bronzes and intricate oil paintings to textile work, contemporary art, Japanese prints, knights in literal shining armor, and pieces from titans like van Gogh, Seurat, Picasso, and O’Keeffe. It’s impossible to see it all in a day, but you can do your darndest.

Loop
The most visited tourist destination in the entire Midwest (sorry, Navy Pier!), Millennium Park is the shining jewel of downtown Chicago—and it lives up to the hype. Morning, afternoon, or evening, there’s always something to gawk at and explore here, from the whimsical architecture and landscaping to free open-air concerts and movies at the Pritzker Pavilion lawn. Of course, you’d be remiss to come here and not take a reflective selfie in the Bean, a 110-ton stainless steel sculpture that marked British artist Anish Kapoor’s first public outdoor work in the US.

Live jazz at Green Mill

Uptown
A city steeped in musical lore, the Green Mill is a storied jazz parlor that’s as historic as it is lively. Al Capone used to be a regular here during Prohibition, and rumor has it that tunnels still linger beneath the floorboards, so you can safely expect plenty of old-timey gangster vibes. Bracing cocktails and soulful jazz performances make for a spirited evening in this well-worn watering hole—an absolute essential for any music aficionado in Chicago.

Improv at The Second City

Old Town
The place that birthed famed comedians like Tina Fey, Stephen Colbert, John Belushi, and Steve Carrell, The Second City is like the holy grail of live comedy. Filled with multiple stages and rooms, and an endless array of vintage ephemera and photographs, this vast Old Town complex is still the ultimate go-to for live comedy in Chicago. There’s something happening every night of the week, at varying price points and themes. You can find amazing sketch comedy here, but The Second City’s improv shows are particularly worthwhile, like Late Night Date Night and Improv Brunch.

South Loop
More than 40-feet long and 13-feet tall, and comprising 250 bones, Sue is not only the most complete T-Rex specimen ever found, but it’s also the largest. And it’s the anchor attraction at the larger-than-life Field Museum on Museum Campus. The massive, 480,000-sq.ft. natural history museum houses fossils and exhibits dating back hundreds of millions of years, from dinos like Sue to European kings and ancient Egyptian mummies. Altogether, there are millions of artifacts on-hand at the Field, displayed in numerous immersive galleries, shows, and events.

House music

Lakeview
Jazz and blues aren’t the only music genres popularly tied to Chicago. House music was created by Black DJs in the ‘70s and ‘80s, from an underground dance scene that blended a buffet of aural flavors like funk, disco, European synth, gospel, and electronic. Popularized by club-goers who were mostly Black, Latino, and queer, house music was a haven from racism and homophobia, and a bastion of late-night revelry. It started at a bygone club in the West Loop called The Warehouse, hence the “house” name, but it lives on at enduring nightclubs throughout the city, especially in and around Lakeview. Berlin and Smartbar are two of the most iconic, and now there are house music festivals around town, like the My House Music Festival in Pilsen.

Pullman Park
Pullman Park | Photo by Jaclyn Rivas for Thrillist

Tours and things to do outdoors in Chicago

Architecture river cruises

River North, Loop
If there’s one blatantly touristy thing like locals actually love, it’s an architecture river cruise. Embarking up and down the Chicago River, and out into Lake Michigan, these sailings are equally fascinating, enthralling, educational, and straight-up fun. There are a few companies that operate comparable cruises, like those run by the Chicago Architecture Center, but all offer an awe-inspiring float through some of the city’s most iconic architectural buildings. From this portion of the Chicago River, sandwiched between the Loop and River North particularly, it feels like sailing through the architectural equivalent of the Grand Canyon, passing by behemoths like the Merchandise Mart, the Marina City “corncob towers,” the one-and-only Willis Tower, and the newest “supertall” tower to join the skyline, the 1,198-foot St. Regis Chicago. There are also evening sunset cruises, as well as special events, and most have full bars on board.

Bucktown
Home to some 614 parks, there’s no shortage of greenery and outdoor space in Chicago, but one of the most unique additions in recent years is the ravenously received 606, a nearly three-mile elevated trail that weaves through Bucktown, Logan Square, and Humboldt Park. A former elevated rail line, it’s been gorgeously retrofitted into a pristinely landscaped pathway for runners, walkers, cyclists, and any other non-automotive mode of transport you can imagine. Hop on and off at your leisure, at numerous entry/exit points along the way, as The 606 conveniently connects neighborhoods, El stops, and thoroughfares.

Hyde Park
Chicago’s iconic architecture isn’t confined to supertall skyscrapers downtown. The hometown of Frank Lloyd Wright, one of the most famed architects in American history, there are numerous abodes throughout Chicagoland that exhibit the star’s Prairie style form. Among the most well-known, and the most accessible for visitors and tours, is the Frederick C. Robie House in Hyde Park. A masterclass in Wright’s signature Prairie style, famously horizontal facades rooted in nature that Wight described as “married to the ground,” the Robie House sports a brick and limestone foundation flanked with overhanging eaves, cantilevered roofs, and tranquil terraces. Inside, a large light-filled living area forms the crux of the property, separated from the dining room by a central chimney. Guided interior tours and self-guided exterior tours are available for booking, to provide a more intricate glimpse into this unique architectural era, and Chicago’s role in residential innovation.

Pullman
It may not be Yellowstone or Yosemite, but Chicago lays claim to a national park site all its own. Located in the Pullman neighborhood on the south side, Pullman National Historical Park became the city’s first national park site when it was designated by President Obama in 2015. And rightfully so, as the history here is extraordinary. Named for George Pullman, a railroad car manufacturer who helped establish Pullman as one of the first fully planned industrial districts in the nation, the park features prominent displays of architecture and innovation, as at the Pullman factory and the Randolph Pullman Porter Museum. The history of Black labor is also paramount, as Pullman was once the largest employer of Black Americans in the US, and the location of the first labor agreement between a Black union and a company. Exploring the neighborhood on foot is a great way to witness the planned community in all its singular glory, but there’s also an illustrious visitor center and distinct buildings to explore, like the ornate Victorian verandah at the Hotel Florence.

Lakefront
For 18 miles, the Lakefront Trail winds its way along Chicago’s shoreline, stretching from Ardmore Avenue on the north side all the way to 71st Street on the southern end. In 2018, a project was completed that separated the bike trail from the pedestrian trail, easing congestion and ensuring a safer experience for all visitors, be it an industrious commuter, a group of joggers, or parents with strollers. Along the way, the trail weaves through prominent attractions in their own right, like Navy Pier, Maggie Daley Park, North Avenue Beach, and Museum Campus. For an up-front view of this striking city, in all its architectural and natural beauty, there’s no better vantage point.

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Ro White is a contributor for Thrillist.