Thinking about moving to the Windy City? First off, don’t call it that. Only tourists do. But for background, the nickname refers to our weather and our windbag politicians, although people more often think about the weather when they think of Chicago. Here’s what it’s really like: The winter is brutal and long. The windchill is sometimes as low as minus 40 degrees, but the summers are glorious—that same wind makes it less humid.
Chicago is the third-largest city in the country (behind New York City and Los Angeles), but it’s simple to navigate. Our skyscrapers are concentrated in the downtown area called the Loop, while more residential neighborhoods fan out to the north, south, and west, with Lake Michigan to the east. If you’re coming from a smaller area, Chicago might feel like an easy place to learn the ropes of city living. Plus, affordable living costs and comprehensive, reliable public transit give Chicago a leg up on most other major cities.
We are the birthplace of the skyscraper and have influenced architecture on a global scale. But we also have plenty of nature: The lakefront trail is 18.5 miles long, and we have 600 parks. There are some cons of city living here, though. We have one of the highest tax rates in the country, crippling state debt, significant segregation, and concentrated areas of deadly gun violence.
To help you make your decision about whether to move to Chicago, below are 18 things you should know about living here.
1. We’re not second rate.
In addition to being known as the Windy City, Chicago is also called the Second City, but that doesn’t mean we’re not as good as other metropolitans. Some say the moniker refers to our population size, which was growing rapidly in the late 19th century and, at one point, came close to New York City’s. It could have also been made up by malicious New Yorkers when the two cities were competing against each other to host a World’s Fair. Regardless, the name stuck after a writer for the New Yorker, who hated the city, published, in 1952, a book about Chicago called The Second City. Chicagoans hated the book, and a few years after it came out, Second City improv reclaimed the nickname by using it for its nationally renowned comedy spot.
Don’t let a misguided stereotype color your perception of the city—Chicago is a leading city in so many ways. We are the birthplace of gospel music, improv comedy, and the skyscraper. Our city was the first to honor and recognize the LGBTQ community in its streetscape, doing so with rainbow pylons in Boystown. And we rank nationally as one of the best sports cities, restaurant destinations, and places to bike.
2. You can get anywhere in the city–on time–for $3.
No nightmare commutes here. Unlike in NYC and LA, you can easily get across town on time on a train or bus. Our subway is called the L, which comes from train cars running on elevated tracks. All L trains stop downtown in the Loop, where many people work.
Beyond that, the Chicago Transit Authority (CTA) has eight train lines and 140 bus routes that run often and on schedule. It’s cheap, too. A single pass costs $2.50, and a transfer to another train line or bus is just a quarter more. Former Chicago Mayor Rahm Emanuel boasted about our transit frequently, citing near-perfect stats for on-schedule trains and buses. His administration invested more than $8 billion into transit and upgraded older stations, like the Red Line’s 95th Street terminal and the Blue Line’s Belmont Gateway.
You might even find yourself wishing for a delay, since about 70 percent of transit stations have significant architecture or art installations. But the ride’s nice too: Being above-ground lets you peer down at backyard chicken coops or watch the busy LaSalle Street bridge as you cross the Chicago River.
Our transit is reliable, but that doesn’t mean we’d advise a daily commute from one end of the city to the other. There aren’t many east-west train lines, and Chicagoans often complain about long trips if they have to transfer to trains or buses. Another grievance is that the Red Line, which ends at 95th Street, doesn’t reach neighborhoods on the Far South Side.
3. Midwestern niceness is real.
Moving to the Midwest is like joining a club that wants you as a member. No one will shove you out of the way when they are in a rush. You can ask for directions, get a thorough answer, and not feel like you’ve annoyed the person you asked. If you take the L long enough, chances are you’ll run into that happy morning conductor who announces the day’s forecast, graciously explains delays, and sings “good morning” as you step off the car. All of the niceness adds up to a kind of camaraderie that makes it easier to get through the day together.
4. Discover a world in a city
You might be surprised to learn that Chicago is incredibly global and diverse. We have 28 sister cities, an initiative that was launched by former Mayor Richard M. Daley, to grow global business relationships and exchange cultures through educational programs. And the neighborhoods reflect the communities that built them: Pilsen’s Mexican food and murals, arts programming at the American Indian Center, stunning Northwest Side Polish-style cathedrals, the Stony Island Arts Bank’s archive of black culture and records in South Shore, Vietnamese noodle shops on Argyle Street, and Indian and Pakistani restaurants on Devon Avenue. If you want to learn more, we have 40 cultural heritage museums, and there are plenty of city organizations that regularly have film screenings, art shows, and history exhibits about various cultures.
5. Chicago is extremely walkable, and it’s hard to get lost.
We are a walker’s paradise! The terrain is flat and sidewalks are pristine. Plus, our easy-to-follow street grid makes navigation straightforward. The intersection of State Street and Madison Street is known as “zero, zero”—everything is calculated based on that. All addresses to the east or west of State are labeled according to if they fall east or west, and all addresses to the north or south of Madison are labeled if they fall north or south. The address numbers increase depending on their distance in miles from “zero, zero,” and there are about eight blocks to a mile, so something in the 800 block is about a mile away.
There are also plenty of places to walk other than the sidewalk. The 606, a former elevated rail line and now linear park, begins in Bucktown. Downtown, there’s the vibrant Riverwalk. The Lakeview Low-Line turned space underneath the L tracks into an artwalk, and the Burnham Wildlife Corridor in Oakland has miles of trails and art installations. And more is coming: A planned trail along the North Branch of the river near Irving Park, 312RiverRun, will have the longest pedestrian bridge in the city, and Pilsen’s Paseo Trail will transform four miles of an old railroad corridor into a linear park.
6. Biking is part of the culture.
Chicago is a great city for biking—there are over 248 miles of protected and conventional bike lanes, such as the one on Milwaukee Avenue, which gets flooded with cyclists during rush hours (and is called the “hipster highway” because of this). Even if you don’t have a bike, Divvy bike share provides 6,000 bikes at 570 docking stations. A single, 30-minute bike-share ride is just $3.
When it snows, major streets are cleared, but bike lanes often aren’t. But, while it’s not the easiest winter ride, bikers are still out pedaling. In 2018, on the coldest day in 34 years, when the temperature was minus 23, 191 people traveled on Divvy bikes. There’s just something about riding in subzero degree weather and seeing a fellow biker. It’s an instant connection, even just in passing.
7. Chicago’s violence isn’t always conveyed accurately in media.
Crime and violence in Chicago is a very complicated—and for many Chicagoans, very personal—issue that goes well beyond often misguided and overhyped stories in the media and national news. In 2016, there was a concerning spike in the city’s homicide rate. However, the following two years saw double-digit declines in homicides and shootings. Like every major city, Chicago has a difficult and painful history of redlining, segregation, disinvestment, and police brutality and abuse. It also has neighborhoods, especially on the city’s South and West sides, such as West Garfield Park and Englewood, that have been disproportionately impacted by the legacy of those problems. Racial oppression and concentrated poverty are more important factors to address than gangs, according to a University of Illinois at Chicago study on the city’s crime patterns and violence prevention. It found nearly 40 percent of Chicago residents live in areas with chronic and concentrated joblessness and poverty, a figure higher here than it is in NYC or LA. Historically, Chicago has prioritized policing over neighborhood investment. However, that strategy is starting to shift as organizations like Mothers Against Senseless Killings, Kids Off the Block, and Chicago CRED create neighborhood watches, start sports leagues, and find kids summer jobs.
8. Winter is long and brutal, but it brings Chicagoans together.
Winter doesn’t mean months spent indoors as long as you get a good coat: Most Chicagoans wear a style that looks like a sleeping bag with a hood. The weather is unpredictable, and winter is rarely over when you think it is, so it’s better to just prepare and accept it. Subzero temperatures for 52 straight hours? Fine! A snowstorm immediately followed by a sunny, warm day in April? Sure. Fifty degrees in February? We’ll take it.
No matter how cold it is, our city has tons to do. Wintertime events include Pitchfork’s Midwinter music festival, beer fests in heated tents, Lincoln Park Zoo’s festive light display, the wooden German market stalls of Christkindlmarket in Daley Plaza, and even a polar plunge into Lake Michigan. One long-held tradition sure to entertain is Dibs season. After a big snow, Chicagoans populate their shoveled-out street-parking spots with foldable lawn chairs, inflatable pools, vacuums, traffic cones and even the occasional recliner and end table.
9. And actually, the winter is beautiful.
On average, the city sees about 36 inches of snow a year. Our first snowfall usually happens in November, and then, there’s silence. In the stillness, all you can hear is the squeak of your boots on the snow. When there’s freezing rain, it coats everything in a layer of ice, which makes the trees look white instead of dark and dormant. The ice sticks like powdered sugar to even the tiniest branches. As winter progresses, the wind, waves, and low temperatures create eerie ice art on lakefront. All along the shoreline, tree branches turn into “crystal” chandeliers and bushes become globs of ice. Benches, light poles, and piers look like they’ve been carved out of ice too.
10. The city bursts with energy during the summer.
No one takes a summer day for granted. If the weather is warm (Chicagoans think 50 degrees is shorts weather), people will be at a park, a beach, or a neighborhood festival.
The Park District goes all out—it hosts hundreds of outdoor movies, concerts, yoga classes, volleyball leagues, stargazing walks, summer camps, fishing at Northerly Island, migratory bird watching, and plant sales. Tour de Fat celebrates bikes and beer, opening day for the Cubs and Sox is like a holiday, and there are endless music festivals (Lollapalooza, Pitchfork, Chicago Jazz Festival, and Riot Fest, to name a few). The beaches and outdoor public pools are packed, and the Lakefront Trail is a constant stream of runners and cyclists.
11. Our city lives for its sports teams and players.
Chicago has eight major league sports teams: the Cubs and White Sox (baseball), the Bulls and Chicago Sky (basketball), the Blackhawks (hockey), the Bears (football), and the Chicago Fire and Chicago Red Stars (soccer). If you’re into college sports, there’s Northwestern University, DePaul, Loyola, Chicago State, and UIC. Plus, the Chicago Marathon happens every fall.
It’s exciting to follow sports in a city with diehard fans, even if you’re not one. When the Bulls were on a hot streak in the ’90s, everyone talked about Michael Jordan and wanted to “be like Mike.” The Blackhawks won Stanley Cups in 2010, 2013, and 2015—the victories brought millions to the celebration rallies, where fans danced to the team’s “Chelsea Dagger” song. When the Cubs won the World Series in 2016, thousands of fans swarmed the streets around Wrigley Field to celebrate the end of the longest championship drought in professional sports. And for weeks afterwards, fans lined up for merchandise at Wrigleyville stores (a record $70 million in retail was sold in the first 24 hours after the win), and the championship parade was the seventh-largest gathering in human history.
But if you’re not enthusiastic about gamedays, don’t live in Wrigleyville, which is home to Wrigley Field and, really, the center of the city’s sports culture. Thousands come to the neighborhood to watch the Cubs and revel at the local bars and restaurants. Avoid the areas around Soldier Field, the United Center, Guaranteed Rate Field, and Wintrust Arena, too.
12. There’s always something free to do.
The city has thousands of events, activities, and places you can go to for free. If you’re an Illinois resident, there are designated days when museums, including the Art Institute and Shedd Aquarium, waive admission costs. The Lincoln Park Zoo, National Museum of Mexican Art, Garfield Park Conservatory, and Cultural Center are free every day. The iO Theater, known for improv, has free weekly performances. The Park District started a series of programming called Night Out in the Parks with thousands of free events in every neighborhood, like movie screenings, theater and dance performances, circuses, yoga classes, and nature walks.
13. We love pizza and hot dogs, but our restaurants have Michelin Stars too.
Outsiders believe our contribution to the dining scene begins and ends with the Chicago-style hot dog and deep-dish pizza. And we do love those staples. Go ahead and try an all-beef dog in a poppyseed bun topped with diced onions, sweet relish, tomato wedges, a pickle spear, spicy sport peppers, celery salt, and mustard. Or get down with a thick slice of cheesy deep dish with a buttery crust. But know that our food scene doesn’t end there.
We have famous tavern-style thin-crust pizza, chicken-fried steak, jibaritos, and Italian beef sandwiches. Chicago is a beer city, but we have a decent reputation when it comes to cocktails too. We’re a city of immigrants, so our global food is also worth checking out—go to Pilsen for Mexican cuisine, Devon Avenue for Indian and Pakastani, and Argyle Street for Vietnamese. To get started, take a look at Eater’s guide to Chicago food.
You should also know we’re home to the James Beard Awards—the Oscars of food. It’ll be held at the Lyric Opera through 2027 and has helped distinguish Chicago as a dining city. Bon Appetit voted Chicago the best restaurant city of the year in 2017, and our restaurants have earned 22 Michelin stars.
14. You can find a home for cheaper than you can in other major cities.
Compared to major coastal cities, you can generally get more space for less money. The median rent for a one-bedroom is $1,821, and a two-bedroom is $2,189. Rent might drop even further as more people buy homes (data suggests homeownership is increasing), a good thing, since rent is currently at a historic high. However, affordable housing for low-income renters is shrinking, and research shows that might be causing people to leave the city, according to a recent report.
If you’re looking to buy a home, the median sale price for a house is $260,000 and properties are spending less time on the market compared to last year. Millennials are the least likely to buy, but in Chicago, 31 percent of millennials own their homes, and the median age for first time homebuyers is 34.
15. It’s easy to find nature in the city.
Chicago’s lakefront is beautiful, but you don’t need to live near it to experience the city’s greenery. There are 600 parks, 70 nature and bird sanctuaries, and a total of 8,800 acres of green space. Chicago has a long history of making the city greener, and even committed to making sure every child was within a 10-minute walk of a park or playground. In the last eight years, the Park District has built or improved more than 1,000 acres of parkland and 377 playgrounds.
Some areas along the Chicago River have been transformed from industrial to recreational with projects like Wild Mile, 312 RiverRun, and Ping Tom Memorial Park. Plus, all around the city, old rail tracks are being turned into vibrant linear parks, like the 606 and the forthcoming Paseo Trail. Our parks have bird sanctuaries, nature preserves, walking paths, art installations, historic fieldhouses, conservatories, and even outdoor pools.
16. Living here will give you an education in architecture.
Chicago embraces its architectural history and is home to major players that shape design conversations. In 2015, the city launched a massive, three-month Chicago Architecture Biennial. The global architecture festival, soon beginning a third edition, invites practitioners and the public to engage in the field’s future through citywide exhibitions and programming. Another architecture festival unlocks the city’s sacred spaces, private mansions, and grand halls: For a weekend, the Chicago Architecture Center’s Open House gives visitors access to hundreds of sites rarely open to the public.
Getting to know Chicago through its buildings is like taking a course in architecture. The skyline is iconic, and is not only home to the first skyscraper, but also the country’s tallest skyscraper (if we’re ignoring One World Trade Center’s controversial symbolic spire). In 1871, the Great Chicago Fire burned down the city and turned it into a blank canvas for ambitious architects, including those who developed the first steel-framed high-rise, which led to the construction of skyscrapers today. Witness the works of Daniel Burnham, Holabird & Roche, Louis Sullivan, Dankmar Adler, Frank Lloyd Wright, Mies van der Rohe, as well as new visionaries like Jeanne Gang, who just landed on Time’s list of the 100 most influential people.
Our residential architecture throughout the city is fascinating too—check out the beautiful, castle-like greystones, the modest workers’ cottages, Chicago-style bungalows, the Bohemian Baroque craftsmanship in Pilsen, the Prairie School-style homes in Oak Park, and Victorian-era mansions on Beer Baron Row in Wicker Park. Each building reflects a part of Chicago history.
17. Travel to either coast is quick.
It’s easy to fly to anywhere in the contiguous U.S. when your homebase is Chicago. There are two major airports: Midway International and O’Hare International, which is the busiest airport in the country when ranked by the number of planes flying in and out each day. And more than 105 million passengers passed through both our airports last year. So if you need to get somewhere, there’s definitely a flight. Or a train! Amtrak runs out of Union Station and is the busiest hub in the Midwest.
18. It can be easy to find your place in Chicago.
Like so many other major cities, Chicago has its challenges. But spend time here and you’ll start to see why Chicagoans love their city: the clear and open lakefront, affordability, and abundant transportation options. Each neighborhood has something to love, from historic theaters to community gardens to baseball stadiums. There are secrets to discover that make living here fun—like where the chocolate-scented air comes from in River North, how to find the tamale man in Logan Square, and what part of Jackson Park has a cherry blossom grove. Chicagoans have a kinship that makes winter survivable and summer incredible, and that you’re welcome to be part of too. If you embrace Chicago, it will love you back.
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