Chicago is the third-largest city in the country, with a population of 2.7 million, and a metro area encompassing 10 million. Situated on the banks of Lake Michigan and the Chicago River, the city grew rapidly grew from a quiet portage point and fur trading outpost in 1833 (population: 200) into an industrial powerhouse and the center of American railway transportation. Home to the first skyscraper, the first Ferris wheel, and the one-time tallest building in the world, Chicago has long been a locus for innovation, education, and culture. It’s a famously diverse city: From its days as a haven for Eastern European immigrants, to its decades as the endpoint for many southern African Americans during the Great Migration, to its current embrace of Mexican immigrants calling the city home, Chicago has long welcomed cultures from around the world. Such diversity, combined with stable infrastructure, a diversified economy, and multiple world-class institutions of higher learning (The University of Chicago and Northwestern, among others) has contributed to a vibrant local culture, home to some of the world’s best restaurants, museums, music, and literature. Chicago’s nickname might be the “Second City,” but that doesn’t keep it from being one of the world’s most important centers for business, culture, and the arts.
Life in Chicago
Transportation
Chicago is the third most populous city in the nation, so it’s just not possible for everyone to drive themselves around. Public transportation is a must, and the Chicago Transit Authority does a fantastic job meeting the needs of Chicagoans. The CTA has comprehensive bus and train lines throughout the city, with an app available to track the system and your account. There are plenty of buses and plenty of bus routes, which also means there are lots of bus stops — if you’re trying to get somewhere in a hurry, a cab might be your best bet. And if you hear someone in Chicago talking about the "L," it’s not a route. The “L” refers to the elevated trains that connect the suburbs and outlying neighborhoods to downtown. (Another rail service, Metra, is aimed at suburban commuters and extends outside of Chicago as far as Wisconsin.)
If you’re hoping to avoid the traffic and bike your way around the city, you’re in luck — kind of. Forbes ranked Chicago as the sixth best city in the country for biking, largely because of the city’s plan to expand bikeways. There are currently about 200 miles of bike trails in the city, and if you run out of road (or steam) you can bring your bike on the CTA.
Where to play
The Magnificent Mile is where you can count on finding just about anything to do. Within this 13-block district — which follows North Michigan Avenue from the Chicago River to Oak Street — you’ll find more than 460 stores and nearly 300 restaurants, plus galleries, theaters, and museums. One of the places to find the most play is Navy Pier, which hosts concerts and events on top of its theme park attractions, including the Centennial Wheel. Then again, you could also head to a game: the Bears, the White Sox, the Cubs, the Bulls, or the Blackhawks all call the Windy City home. Better yet, take a tour of the city from where you can see its skyline best: Lake Michigan. Boat tours follow the shoreline while treating you to food and drinks.
Attractions
Chicago is home to perhaps more famous landmarks than any city in the country short of New York. At 1,451 feet, The Willis (formerly Sears) tower is the most noticeable, and a visit to the 103rd floor can offer you the best view of the city (and a case of vertigo, if you step onto The Ledge, a glass floor extending off the side of the building). One of Chicago’s premier attractions is its architecture, and a river cruise can be a fantastic way to appreciate some of the city’s magnificent buildings. Navy Pier on a summer day is a classic Chicago outing: A ride on the pier’s famous Ferris wheel can be fun for the whole family or provide the perfect spot for a romantic sunset date. Also lakeside is The Museum Campus, which connects 10 acres and three museums: The Adler Planetarium and Astronomy Museum, The Field Museum, and Shedd Aquarium, one of the nation’s best.
Dining
Chicago is famous for its deep dish — we’ll leave the argument about whether it’s actually pizza for another website — its iconic hot dogs (tomatoes, hot peppers, and celery salt required, and don’t even think about ketchup), and its sliced beef. But what many don’t know is that it’s the tamale capital of the U.S., home to the largest mass producer of the beloved Mexican standard in the country. For a true taste of Chicago’s melting pot, try a Mother-in-Law: a tamale in a hot dog bun, covered in chili.
Chicago’s dining scene isn’t solely dedicated to food you can eat with your hands, though. Its iconic steak houses — David Burke’s Primehouse, Gene and Georgetti, and countless others — serve up enormous cuts of beef, callbacks to Chicago’s history as the meatpacking center of the world. And in recent decades the city has become one of the top destinations in the world for fine dining, host to dozens of Michelin-starred restaurants, including Grant Achatz’s three-star phenomenon Alinea, south side warehouse lab El Ideas, and Parachute, an Avondale spot serving inventive takes on Korean cuisine. And that’s not even scratching the surface.
Bars
Since Prohibition, when Al Capone and other Chicago gangsters made fortunes transporting and selling illegal liquor, Chicago has always been one of the Midwest’s best places to find a drink. The city is full of bars, from classic basement dives like Rosa’s Lounge in Lincoln Park, to old-school Polish places like The New Polonia, to reservations-only cocktail lounges like The Ladies Room.
If you’re looking for a club — and in the birthplace of house music, you should be — Primary and Smartbar offer state-of-the-art sound systems and some of the best DJs on the planet, as well as drinks. For an inside look at the various intoxicating liquids you’ll surely be pouring down your gullet, consider a tour of one of Chicago’s many breweries and distilleries, like Goose Island, Half Acre, 5 Rabbit, North Shore Distillery, Few, or Koval (to name a few).
Or you can just belly up to the bar, order an Old Style, and try to stomach a shot of Jeppson’s Malort, the beloved, wormwood-inflected bäsk liquor that’s been making non-locals gag since the 1930s.
Culture
Chicago is home to some of the most-decorated cultural institutions in the country, and attempting a full list would be a fool’s errand. A few of the highlights include The Art Institute, which houses over 300,000 works of art (including Edward Hopper’s iconic Nighthawks, Picasso’s The Old Guitarist, and Grant Wood’s American Gothic) and draws over a million visitors per year; The Field Museum, one of the oldest and best natural history museums in the country; and the internationally acclaimed Chicago Symphony Orchestra. There is a lively tradition of large-scale public art, with sculptures like Anish Kapoor’s Cloud Gate (you might know it as “that giant mirror-thing in Millennium Park”) drawing art-lovers and tourists alike.
Musically, Chicago has birthed several distinct genres of music: most notably Chicago Blues, which emphasizes electric guitar and harmonica, and House, whose four-on-the-floor drums and skittering hi-hats exploded out of Chicago in the early ‘80s. In the ‘90s, Chicago also became a hotbed for alt-rock and indie-rock, with acts like Smashing Pumpkins, The Jesus Lizard, and Liz Phair gaining national renown, along with legendary producer Steve Albini. Currently, Chicago serves as home base for online tastemakers Pitchfork, whose Pitchfork Festival, along with Lollapalooza, brings thousands of visitors to the city every summer for live music.
And let’s not forget comedy. Since 1959, The Second City improv theater has served as a finishing school for aspiring comedians, many of whom — Harold Ramis, Stephen Colbert, Tina Fey, Amy Poehler, Amy Sedaris — have gone on to national fame. Satirical news source The Onion (originally from Madison, WI) also now calls Chicago home.
Events
There is a different festival in Chicago every week of the year — and probably even more than one. A handful of the many music festivals that put Chicago on travel plans include Lollapalooza, Pitchfork, Chicago World Music Festival, and the Chicago Jazz Festival. For food fests, there is the Taste of Chicago — which incorporates live music with chef exhibitions — and the Chicago Food Truck Festival. Looking for art? Try Expo Chicago, which fills Navy Pier with contemporary and modern artworks. Chicago also hosts the largest and longest-running free air show each year since 1959. Then there are the regular weekly events, such as the Millennium Park concert series that spans the summer months, or the Chicago SummerDance series in Grant Park. If you’re bored, you just aren’t trying.
Shopping
Chicago is rife with world-class shopping districts. But the main draw for shopping fanatics is the Magnificent Mile — 13 blocks along Michigan Avenue. The Mile is home to many of the best department stores, boutiques, and jewelry stores retail has to offer, such as Burberry, Chanel, OSKA, Bloomingdale’s, Saks Fifth Avenue, and dozens more. Another major shopping mecca is right in the Loop: Macy’s on State Street. This Macy’s has proven itself to be so significant to the local area — with its vaulted fifth-floor ceiling made from 1.6 million pieces of Tiffany glass — that it earned itself a spot on the National Register of Historic Places. The Loop also offers dozens of other big-name stores, such as Nordstrom Rack, Estee Lauder, Target, and Urban Outfitters. If you’re looking to explore some bohemian shops in one of the more artistic neighbourhoods in the city, then Wicker Park is an excellent place to spend an afternoon. It’s farther from the city center but is worth the trip.
Sports
Da Bears, Da Bulls… and also The Blackhawks, The White Sox, and the Cubs. Chicago is a powerhouse sports town, home to teams in every major American sport. And though the Bears — one of two surviving foundational teams for the NFL — haven’t been doing too well in the NFC North recently, local fans have had plenty to cheer about on the hockey front, as the Blackhawks have won three Stanley Cups in the last six years. The Chicago Bulls are perhaps the most famous franchise in the history of the NBA, thanks to one Michael Jeffrey Jordan and the six championships he brought to the city. You can see a 12-foot-tall statue of His Airness mid-dunk, outside the United Center where both the Bulls and the Blackhawks play.
If you’re a baseball fan, you know that Chicago is home to two teams of the oldest teams in the sport’s history: The White Sox, who play on the South Side of Chicago, and The Cubs, who play on the North Side.
Outdoors
One of the best things about Chicago is that it sits along the beautiful shores of Lake Michigan. The Lakefront Trail stretches for 18 miles along Lake Michigan, perfect for biking or taking a stroll, with volleyball and tennis courts, beaches, and baseball diamonds along the way. Try your hand at sailing, canoeing, kayaking, paddle boarding, and other waterborne activities along the lakeshore or on the Chicago River. To enjoy some of the most beautiful scenery on solid ground, head to the Morton Arboretum, which encompasses more than 1,700 acres of natural plants and trees and several trails. For more nature within city limits, the Lincoln Park Conservatory has exotic plants in four themed display houses — Palm House, Fern Room, Orchid House, and Show House — that stay green and gorgeous even through the cold Chicago winter.