Chicago was incorporated as a city in 1837. It has since become the third-largest city in the US and a Midwestern hub of art, culture, sports, food, architecture, entertainment, beautiful parks, and more. Occupying more than 230 miles along the Lake Michigan coast, Chicago offers residents all the benefits of a big city modern living with the relaxed, down-to-earth mindset of the Midwest.
As of the writing of this guide, Chicago has a population of more than 2.7 million residents. Like most major cities in the US, the city is a melting pot with a diverse population. Chicago is 33% White, 28% Hispanic or Latino, 29% Black or African American, and 6% Asian.
It’s no secret that Chicago is cold—in the winter months, temperatures reach an average low of 22 °F—but in spring and the summer, it warms up to the 70s and 80s. While outdoor festivals, boating, and pool days are reserved for those latter seasons, the cold weather doesn’t stop Chicagoans from going outside and taking advantage of all their city has to offer.
Apartments in Chicago run the gamut from affordable to expensive, with everything from older, more historic buildings to modern options with popular rooftop pools, lounges, working spaces, dog spas, and any other amenity residents could crave.
Chicago has 77 different neighborhoods, each with their own distinct vibe. Live in The Loop, which has jaw-dropping architecture and the Chicago Riverwalk, then walk to Magnificent Mile for the city’s best shopping. Not too far away, Gold Coast and River North offer luxury storefronts and lots of art and design galleries. Explore the quirky street art, vintage boutiques, record stores, and independent coffee houses and bookstores in Wicker Park, or stay in Wrigleyville to be steps away from Wrigley Field. Those who love to be on the water can choose from a variety of neighborhoods bordering Lake Michigan, like Edgewater, Streeterville, or Lakeview.
While you’ll see a lot of cars driving through Chicago, most residents don’t drive. (Parking is incredibly expensive in Chicago, and locals can either walk or take public transportation to anywhere they need to go.) For those who do prefer a car to other options, rideshares and taxis are available.
The Chicago Transit Authority (CTA) has a very efficient public transportation system, with “L” trains servicing over 140 stations all over the city. An abbreviation of the word “elevated,” most trains are above-ground, with some at street-level or underground. Of its eight lines, the Blue Line and Red Line run 24 hours a day, seven days a week, traveling between Chicago O’Hare International Airport and Downtown Chicago and the North and South Side of the city, respectively. The CTA also offers 129 bus routes with stops all over Chicago.
Those who live outside of Chicago proper can hop on the Metra train for quick, affordable service to and from neighboring suburbs and Downtown Chicago. Most visitors fly in and out of Chicago O’Hare International Airport or Chicago Midway International Airport, with flights to major airports worldwide.
Chicago residents love to ride their bikes. With over 200 miles of bike lanes, 19 miles of lakefront bike paths, and 13,000 bike racks, Chicago claims the country’s second-highest percentage of residents who bike to work. When the weather is nice, take advantage of Chicago’s water taxis for a fun, cheap way to get to the most popular parts of the city via Lake Michigan or the Chicago River.
People travel from all over the world to indulge in Chicago’s renowned food scene. Boasting some of the best restaurants in the world, it has 24 Michelin-starred restaurants, 58 Bib Gourmand recommendations, and award-winning haunts by star chefs like Rick Bayless, Andrew Zimmerman, Stephanie Izard, Grant Achatz (of Chicago’s own three-star Michelin and one of “The World’s 50 Best Restaurants,” Alinea), and more. In true Midwestern fashion, the fame of restaurants in Chicago hasn’t made them stuffy or unwelcoming—patrons get friendly dining experiences and, even in the nicest of places, jeans are still the norm. The food scene is as diverse as its residents, with a dedicated Chinatown, Greek Town, Little Italy, and Polish Downtown, plus a slew of steakhouses receiving rave reviews. Chicagoans know how good they have it with restaurants, so make reservations weeks, or even months, in advance to dine at the city’s hottest spots.
When in Chicago, there are tons of dishes you have to try (don’t miss the Italian beef sandwiches!), but it’s most famous for deep-dish pizza and Chicago dogs. Deep-dish pizza is exactly as it sounds. Instead of a standard thin crust, this ‘za has one that’s two or three inches deep. It’s cooked in what looks like a cake or pie pan, with oil beneath it so that the crust fries just slightly. Then it’s layered with ingredients—the cheese goes on the bottom, different vegetables and meats are in the middle, and there’s a chunky tomato sauce on top—creating a pizza so thick that you have to eat it with a knife and fork. Try it at the place where it was invented, Pizzeria Uno, or at two other local joints known for their pizza pies, Giordano’s and Lou Malnati’s Pizzeria.
The Chicago dog is the city’s version of a classic hot dog, with an all-beef frank, a poppy seed hot dog bun, mustard, pickle relish, chopped onions, tomato, sport peppers, celery salt, and a pickle spear. Before you ask, no, they didn’t forget the ketchup! There’s no ketchup on a Chicago dog. The most famous ones are at Portillo’s, a Chicago street food favorite since 1963.
Like the restaurant scene, bars here offer impressive drink menus in unpretentious settings. Go to Lost Lake or The Violet Hour for award-winning cocktails, order a glass of wine at Spiaggia (it’s earned James Beard nods for “Outstanding Wine Program”), or grab a beer at any of Chicago’s 200+ breweries.
Chicago is the shopping capital of the Midwest, and it all centers around Magnificent Mile: the mile-long part of North Michigan Avenue, between Oak Street and the Chicago River, that’s lined with stores that would make Fifth Avenue shoppers squeal. With a mix of 460 stores, from standalone stores to multi-level malls hidden in towering high-rises, Magnificent Mile prides itself on having shopping options for every budget. Stroll from one end to the other—Magnificent Mile is always buzzing with excitement—and you’ll see the giant Louis Vuitton store, the flagship Crate & Barrel (it’s actually shaped like a barrel), Tiffany & Co., Saks Fifth Avenue, and the largest Polo Ralph Lauren in the world, as well as more standard options like H&M, TJMaxx, Nike, Ulta, and Levi’s. Parents and their doll-loving children won’t want to miss the giant American Girl Place, which has become one of the most-visited stores in Chicago. Just off of “the Mile,” Oak Street is Chicago’s luxury shopping district with names like Giorgio Armani, Escada, Prada, Jimmy Choo, Harry Winston, and more.
Other neighborhoods are known for more specific shopping. In the Chicago Loop, you’ll find both discount department stores and “Jewelers’ Row,” the city’s own diamond district. In that same neighborhood, State Street is home to one of the largest department stores in the world, Macy’s, which takes up a whole city block and has the largest Tiffany glass mosaic dome in the country. River North is known for its historic art and gallery district, its home design stores, and for having the world’s largest commercial building, the 1930’s-built Merchandise Mart, which is filled with showrooms for interior design. If you like to create your own definition of “fashion,” shop through the independent boutiques in Wicker Park.
Chicago has everything—arts, culture, history, good sports teams, beautiful outdoor spaces, and activities and attractions for all ages. Plus, with its reliable public transportation system, it’s easy to get to any of Chicago’s must-do experiences at any time of day. The city’s most well-known sites are a great place to start. Ride the elevator to the top of the Willis Tower, and see the view from its Skydeck. Stroll through Millennium Park to take a picture in front of Cloud Gate (“The Bean”), catch a concert or movie in the outdoor amphitheater, or just admire its gardens. The famous Navy Pier is a world of its own. Go there to grab food or a drink by idyllic Lake Michigan, explore Crystal Garden’s glass atrium with 80+ palms and light-strung foliage, ride the Centennial Wheel, or take your kids to the 4,000-foot Amazing Chicago’s Funhouse Maze.
If it’s arts and culture you seek, check out Chicago’s museum scene, where the word “largest” is a common theme. The Art Institute of Chicago has the largest collection of Impressionist art outside of the Louvre. The Field Museum has the largest Tyrannosaurus rex fossil ever discovered. At the Museum of Science and Industry, you can see an actual U-505 submarine. Shedd Aquarium is one of the largest aquariums in the world, while Adler Planetarium is the oldest one in the country. For the best classical music, theater, and opera in town, see what’s playing at The Goodman Theatre, Chicago Shakespeare Theatre, Chicago Theatre, Lyric Opera, or the Chicago Symphony Orchestra. Second City is still acclaimed for its improv—it’s where stars like Bill Murray and Stephen Colbert got their start. For a truly special Chicago experience, take the Chicago Architecture Foundation boat tour and see the city’s hidden gems from its sparkling green-blue river.
Chicago has plenty of outdoor areas to explore. Wander along the 18-mile Lakefront Trail, which sidles up to Lake Michigan’s shoreline—and if the sun is out, get a tan at North Avenue Beach. Chicago loves its Cubs, and whether you’re a baseball fan or not, you’re sure to enjoy taking in a game at the revered Wrigley Field. If you’re traveling with kids, take them to the free Lincoln Park Zoo or to Maggie Daley Park, where you’ll find enchanting play areas designed after classic children’s books, rock climbing, mini-golf, and the Skating Ribbon, which turns into an urban ice skating rink during the winter months. In summer, go boating on the Chicago River and Lake Michigan.
With so much to do and see in Chicago, the city is an attractive place for college students. Some of the nation’s top universities can be found here, including The University of Chicago, Northwestern University, Loyola University Chicago, University of Illinois Chicago, DePaul University, Wheaton College, and Chicago State University.
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