Considering Moving to Chicago? Ten Things You Need to Know!

The Second City. The Windy City. The City of Broad Shoulders. The Third Coast. Chicago has a variety of colorful and historic nicknames, and while each of them captures part of its unique identity, only those who call it home truly know that Chicago is all of these things at once – a global city that offers its residents amenities, lifestyles, and housing that rival any other city. While inhabitants of the East and West Coast often overlook Chicago, or think of it as the place to transfer flights while heading cross country, anyone who has decided to put down roots and stay awhile will argue that Los Angeles and New York don’t offer anything that you can’t get cheaper and friendlier in the Midwest’s capital.

Yes, it does snow and get cold in the winter. Yes, it is a bit flat and nondescript when compared to the mountainous vistas surrounding cities like San Francisco and Denver. But nestled on the shores of majestic Lake Michigan, Chicago’s unique history and blend of cultural influences offer individuals and families alike home that never gets boring or repetitive. World class restaurants like Alinea sit shoulder to shoulder with cozy dive bars where the locals cheer on the Bears, Bulls, Blackhawks, Cubs, and White Sox. Kids grow up enjoying unparalleled cultural institutions like the Field Museum, Museum of Science and Industry, Shedd Aquarium, Adler Planetarium, and Lincoln Park Zoo. Some of the best public schools and most prestigious universities in the country offer world-class educational opportunities for all ages. And major companies from McDonald’s to Morningstar to Google to Uber have national and regional headquarters here, offering plentiful career paths that maintain the thriving downtown and make Chicago a commercial center that powers the world.

Is your interest piqued? We don’t blame you. If you’re thinking about moving to Chicago, you’re making a smart decision. To help make it easier for you, we decided to collect some of the best reasons to consider for anyone thinking about putting their own roots down in “The 606”.

Not-so-interesting facts about Chicago:

  • Population (Chicago Metro): 2,705,944 (2018)

  • Population (Greater Chicago Area): 9.5 million (2018)

  • Unemployment rate in Chicago: 4.1% (August 2019)

  • Median Household Income: $55,198 (2018)

  • Average Commute Time: 58.5 minutes (includes suburban commutes into city)

Reason #1: From apartments to historic mansions, condos to townhomes, there is a home for everyone moving to Chicago


One of the biggest attractions of the Chicago real estate market is the diversity of neighborhoods, housing stock, and living options available for anyone thinking about making the move. From the high rise apartment and condo towers of the Loop, Gold Coast, and River North, to the leafy streets lined with single family homes of all shapes and sizes in family-friendly areas like Lincoln Park, Lakeview, and Lincoln Square, there’s something for everyone.

Residents looking for the quintessential city life when moving to Chicago often look to areas around the Loop, Chicago’s downtown and heart of its historic skyline. Brand new construction has exploded in these neighborhoods over the past two decades, with cutting-edge LEED-certified buildings rising next to historic skyscrapers that provide the perfect array of options for anyone with their heart set on a downtown apartment and the lifestyle that comes with it.

Meanwhile, while downtown catches the eye when driving into the city, any Chicagoan will tell you that the true heartbeat of the city can be found in the dozens of unique neighborhood areas that sprawl out for miles in every direction from downtown. To the north, the various lakefront neighborhoods feature both high rises and single family homes, with every side street offering quiet, safe blocks perfect for raising kids while still offering all the benefits of living in the big city. Historic ethnic neighborhoods like Andersonville (Swedish), Lincoln Square (German), Pilsen (Mexican/Eastern European), Little Italy, Greektown, Chinatown, and a dozen others all maintain their cultural roots while modernizing every day.

Reason #2: You’ll never have a boring day or night out

They say that New York is the City that Never Sleeps, but Chicago gives it a serious run for its money. With dozens of Michelin-starred restaurants, world-class theaters like Steppenwolf and the Goodman, concert venues and festivals like Huntington Bank Pavilion and Lollapalooza, and some of the biggest names and teams in professional sports (Michael Jordan and the Bears ring a bell?), you could spend the rest of your life in Chicago and still find things you haven’t experienced yet.

But it’s not just the big names and bright lights that offer entertainment in Chicago – as a city with a strong working class tradition, some of the best eats and drinks in Chicago can be found on quiet side streets or off far-flung CTA stops throughout the city. From neighborhood taquerias to cozy and friendly neighborhood pubs, to the popular street festivals that seem to dot the city on every single weekend in the spring and summer, to the world-class farmer’s markets that bring in fresh produce, meat, baked goods, and crafts from farms and vendors throughout the Great Lakes region, Chicago is just as popular among working class families as it is among corporate hotshots.

There are also limitless places to take family and friends who come to town – while we will cover these more further into our guide, one especially worth mentioning is Navy Pier. Protruding well into Lake Michigan and easy-to-find due to its large Ferris wheel offering jaw-dropping views of the skyline and the lake alike, Navy Pier is often considered a must-see for anyone visiting or moving to Chicago for the first time. It’s also home to an IMax theater, as well as the Chicago Shakespeare Theater, which offers world-class Shakespearean productions for adults and children alike.

Reason #3: Some of the best schools in the country, from elementary to university

When you say Northwestern or the University of Chicago, no matter where you are in the country, people know what you are talking about. The two iconic Chicago universities (one just north of the city in Evanston, the other in the historic Hyde Park neighborhood) are perhaps the most famous names in Chicago education, but they form just the tip of the iceberg. DePaul, Loyola, the rapidly rising University of Illinois-Chicago, and the Illinois Institute of Technology allow Chicago to rival more popular urban areas like Boston as a center for higher learning and research, as well as all of the other benefits that top universities bring to a city.

Even more impressive are the array of top-ranked public schools that open their doors to students of all ages in the city every day. With the Chicago Public Schools on a rapidly rising track of improvement over the past decade, CPS not only offers some of the best high schools and elementary schools in the nation, but also a variety of neighborhood public schools that provide quality public education right in the neighborhood for families of all means.

Reason #4: You’ve heard about the snow and wind, but the other six months should be what you’re talking about

Ask any Chicagoan, and they’ll tell you truthfully that it can get cold and snowy from November to April. It’s a fact of life in the Midwest, and the Windy City is no different. However, what many people don’t know is that during the rest of the year, Chicago comes to life with beautiful weather that brings the city and its residents to bustling vibrance.

Along Lake Michigan, miles and miles of sandy and clean public beaches just blocks (or an easy bus or train ride) from the various neighborhoods offer the chance to make every day a beach day. Lakeside cafes and bars offer cold drinks and tasty treats for adults and kids alike. The popular Lakefront Path is packed with bikers and joggers enjoying the fresh air and refreshing lake breezes, while the recently opened 606 elevated path offers a Midwestern take on New York’s popular High Line trail, running from near downtown to various neighborhoods on the West Side.

Meanwhile, throughout the city are acres and acres of public parks, forest preserves, and green space that feature everything from public swimming pools to recreational sports leagues and summer camp opportunities for youngsters. Following the original plan of Chicago’s legendary architects, Daniel Burnham and Frederick Law Olmstead, Chicago was conceived from the start as a city that offered its residents opportunities for peace and quiet just blocks from every door. The parks also host several famous music festivals, including Riot Fest and Lollapalooza, where on summer weekends thousands of attendees from across the country flock to hear live music from some of the biggest names in music. In the north, Lincoln Park stretches for miles along the lakefront, home of the Chicago History Museum, the free and family-friendly Lincoln Park Zoo, and the Green City Market, one of the oldest and largest farmer’s markets in the country.

Meanwhile, downtown Grant Park has always been Chicago’s meeting place, centered around the picturesgue Buckingham Fountain with its photogenic skyline backdrop.

If all that isn’t enough, there are also the two newest additions to Chicago’s parkscapes, Millenium Park and Maggie Daley Park, both located at the north end of Grant Park proper. Millenium Park is home to several architectural marvels, including the Lurie Gardens, the famous Cloud Gate (more commonly known as the Bean for its distinct shape), and the Pritzker Pavilion, a stunning bandshell that plays host to free concerts in the summer. Nearby, Maggie Daley Park includes a giant playground, climbing wall, and during the winter, a skating ribbon for everyone to enjoy.

Reason #5: But winter is pretty cool in Chicago too!

Sue the T-Rex

We’re serious! While Chicago gets a bad reputation for snowy streets and cold winds off the lake, you’ll be stunned at how the city makes the best of even the worst weather. From the beautiful holiday decorations and lights that sparkle up the neighborhoods, to the outdoor skating rinks that spring up throughout the city during its coldest months, true Chicagoans know that winter is no excuse not to enjoy yourself.

One of the most popular winter attractions for Chicagoans is the Christkindlmart, a German winter marketplace that takes over downtown Daley Plaza during the holiday season, offering unique crafts, gifts, mulled wine, and tasty treats that are fun for the whole family to enjoy. Meanwhile, forest preserves and parks throughout the city become wonderful places for breaking out your cross-country skis during a heavy snowfall.

Reason #6: All the culture you could ever ask for

Raised Bridge in Chicago

If the weather isn’t cooperating, never fear – the attractions in Chicago aren’t just out in the elements. Chicago offers dozens of museums and historic sites big and small, with many free all of the time or heavily discounted for city residents.

Downtown, the Museum Campus includes three world-class museums within shouting distance of each other. The Shedd Aquarium, Adler Planetarium, and Field Museum (natural history) can be visited time and time again while still offering something new each time, with rotating exhibits that always offer a new experience. Along Michigan Avenue, the Art Institute hosts one of the most impressive and valuable collections of classical and modern art in the world, made famous by the movie Ferris Bueller’s Day Off. On the South Side, the Museum of Science and Industry offers hands-on science experiences and exhibits that can have your kids busy for hours, if not days.

But those are just the big names in culture – equally central to Chicago’s identity are its music, theater, and cultural institutions dotted throughout the neighborhoods themselves. Major productions of musicals and plays rotate through world-famous venues like Steppenwolf, the Goodman, the Chicago Shakespeare Theater, and the Oriental Theater, along with dozens of smaller venues. The Second City Comedy Club, starting point for legendary names like Belushi, Murray, Aykrod, Fey, Colbert, Carell, and dozens of others offers shows every week that leave guests belly laughing until they cry. Music lovers, never fear – aside from the major music draws, historic venues like Kingston Mines for blues lovers or the Green Mill jazz club (a former speakeasy and haunt of legendary gangster Al Capone) offer intimate settings for live music as well. For dance and higher culture, the Lyric Opera, Joffrey Ballet, Hubbard Street Dance Chicago, and the Giordano are world-renowned for their ensembles and offerings.

Reason #7: Travel – both locally and globally – is a breeze!

While we’ve given you some great reasons to move to Chicago, we know that everyone wants to be able to get around, and get away, easily when they pick a place to put down their roots. In this aspect, Chicago is no slouch – public transportation in Chicago is among the most affordable, convenient, and well-maintained not only in the U.S., but in the world.

The Red, Brown, Green, Pink, Blue, Yellow, and Purple lines of the CTA elevated trains run outwards from downtown like spokes on a wheel, offering reliable and convenient access between any two points in the city for just $2.50 a trip. Meanwhile, over a hundred different bus routes criss-cross the city as well, running regular service even into the early morning hours. Divvy bikes, which can be rented by the hour or by the day, are great for cruising Chicago’s miles of dedicated bike lanes and paths (or just bring your own!). And just this past summer, Chicago added rental electric scooters, the same ones emerging in cities throughout the country and the world, offering an entirely new and fun way of getting around.

If you need to get out of the city, never fear – Chicago makes that simple too! O’Hare International Airport, one of the largest and busiest airports in the world, offers hundreds of flights a day, with direct connections as close as Milwaukee and as far away as Sydney or Dubai. Midway International Airport serves the South Side of the city, and gives you even more options. Meanwhile, Amtrak, Greyhound, and Megabus all offer convenient bus and train routes throughout the Midwest. No matter what your travel budget, you’ll be able to get there and back whenever you need to.

Reason #8: The people make the city great

Cubs Win

While many big cities get a bad reputation for being full of impatient, hurried, or downright mean people (here’s looking at you, New York), Chicago reflects the Midwestern values of the region that surrounds it. Chicagoans take pride on being friendly, helpful, and patient when compared to many of their big city brethren. Whether you need directions or a ride, help with installing siding on your home or a teacher or coach for your kid, Chicagoans take pride on wowing visitors and longtime residents alike with their welcoming attitudes and neighborly demeanors. When you move to Chicago, you may be moving to the big city – but you’ll get a lot of the best of small-town attitudes along with all the big city feel.

Reason #9: The best sports town, hands down

Chicago Skyline at Night

On any given street in Chicago, one thing that immediately catches your eye are the numerous sports bars and team flags that line neighborhoods north, south, and west. Chicago’s sports teams (and their crazed fans) are as central to the city’s identity as the landmarks, Lake Michigan, and deep-dish pizza. Soldier Field (the Bears), Wrigley Field (the Cubs), the United Center (the Bulls and Blackhawks), and Guaranteed Rate Field (the White Sox) all draw throngs of fans who support their teams with passion and fervor that rival any city in the country.

But you don’t need to have grown up in Chicago to find something to love about Chicago sports. From the joy of enjoying a hot dog, crackerjacks, and ice cream on a sunny summer day at the baseball games, to escaping out of the snow to see the Bulls and the Blackhawks compete to add more titles to their illustrious histories, enjoying Chicago sports is great for friends, family, and the kids alike. In addition, the Chicago Fire soccer team has relocated to Soldier Field, giving Chicagoans another team to support during the summer months. Whether you are a long-time sports fanatic, or looking to experience a big-time pro sports environment for the first time, Chicago offers as many options as any major city.

Reason #10: A city with a unique and unbelievable history

Chicagoans love the stories, people, and places that have come together to build the city that you see today. From gangsters to architects, tragedies to scandals, Chicago’s history stands apart from other American cities, with a cast of colorful characters known worldwide. Many have heard the story of Mrs. O’Leary’s cow, which according to legend, kicked over a lantern that started the Great Chicago Fire. While this is often considered an urban legend, the Fire is essential to understanding modern Chicago, which was redesigned and rebuilt into the modern architectural wonder we see today. From turn-of-the-century skyscrapers like the Wrigley Building, Tribune Tower, and Board of Trade building towering over downtown, to modern marvels like the Willis (most Chicagoans still call it the Sears), the Hancock Building, Aqua, and the Aon Center, the breathtaking skyline of today wouldn’t be possible without the Fire creating a blank slate for architects, builders, and designers over a century.

Meanwhile, the streets of Chicago have been walked and stalked by noteworthy figures of all stripes, good and bad. Legendary gangster Al Capone is synonymous with the 1930s era of gangsters that Chicago was often associated with, while authors like Carl Sandberg, Nelson Algren, Studs Terkel, and Sandra Cisneros built their literary reputations living in the city. Meanwhile, Chicago’s notorious political scene is not only responsible for larger-than-life figures like Richard Daley (senior and junior), but also for being home to President Barack Obama, who worked as a community organizer and politician in the city for years and called the Kenwood neighborhood home.