Moving to a new city is a big decision, and Chicago – the famous “Windy City” – often finds itself on people’s shortlists. As the third-largest city in the United States (with nearly 2.7 million residents), Chicago offers a blend of urban excitement and Midwestern charm that few places can match. It’s a city of towering skyscrapers and lakefront parks, world-class museums and neighborhood street festivals. If you’re wondering, “Should I move to Chicago?”, this guide will break down what life in Chicago is like and the many good reasons that draw people here.

Related: Chicago Apartment Spotlight – Coppia

What Is Chicago Like?

Chicago is a vibrant metropolis located on the shores of Lake Michigan. It boasts a rich history, a diverse economy, and a culturally diverse population, making it an appealing destination for newcomers (blog.aptamigo.com). In Chicago, you get all the perks of a major city – think bustling downtown streets, iconic architecture, and endless entertainment – without the sky-high price tag of New York or San Francisco (blog.aptamigo.com). In fact, despite its size and status, Chicago doesn’t even crack the top ten most expensive U.S. cities, which is great news if you’re coming from pricier markets (blog.aptamigo.com).

Life in Chicago means experiencing four distinct seasons. Summers are warm and lively, with residents flocking to outdoor patios, rooftop bars, and the 26 miles of lakefront pathways and beaches (chicago.gov). Winters are cold and snowy – Chicagoans famously endure blizzards and frigid winds off the lake – but the city is well-equipped for it. Many say that enduring a tough winter only makes the summer that much sweeter. And once the weather warms up, the city truly comes alive: nearly every weekend brings a different street fair or music festival, and locals take full advantage of the sunshine.

Another hallmark of Chicago life is its neighborhoods. The city is often described as a “city of neighborhoods” – 77 distinct community areas and over 100 neighborhoods (chicago.gov), each with its own character. Whether you prefer the historic brownstones of Lincoln Park, the trendy restaurants of West Loop, the artsy vibe of Wicker Park, or the beachy feel of Lakeview, there’s a neighborhood that will feel like home. (For help picking an area, check out a handy Chicago neighborhood guide to learn each locale’s vibe, proximity to transit, nightlife, and more.) Chicago’s layout makes it possible to find a close-knit community in a big city – you can enjoy a residential, community feel while still being minutes from downtown excitement.

Culturally, Chicago offers an inviting mix of Midwestern friendliness and big-city energy. Strangers might say hello or offer directions on the street – a reflection of that famous Midwestern warmth (timeout.com). Chicagoans are generally seen as friendly, helpful, and genuine, striking a nice balance between big-city brusqueness and small-town hospitality (blog.aptamigo.com). This welcoming atmosphere can make it easier for newcomers (including young professionals moving alone) to settle in and meet people. Overall, life in Chicago means living in a dynamic urban center that still manages to feel approachable and community-oriented.

Good Reasons to Move to Chicago

If you’re considering a move, here are some of the best reasons why Chicago attracts so many new residents. From career opportunities to food to fun, Chicago delivers on all fronts.

Thriving Job Market and Diverse Economy

Chicago is an economic powerhouse of the Midwest, with a job market that spans a wide range of industries. The city’s economy is remarkably diverse – the most diverse of any U.S. metro area – including finance, tech, healthcare, education, manufacturing, and more (worldbusinesschicago.com). This means there are opportunities for young professionals in almost any field. Major companies have a strong presence here: Chicago is home to the headquarters of 24 Fortune 500 companies (think giants like McDonald’s, Boeing, Walgreens, and United Airlines, among others) (axios.com). The city has also emerged as a tech hub in recent years, launching renowned tech firms and attracting offices of companies like Google, Salesforce, and Uber (nmrk.com). In fact, Chicago’s tech sector grew 18% over the past decade, adding over 100,000 jobs in technology fields – great news if you’re in IT or startups (nmrk.com).

For those in finance and business, Chicago has long been a center of commerce. It hosts the Chicago Board of Trade and Chicago Mercantile Exchange, and it has the third-highest employment in finance and insurance nationwide (worldbusinesschicago.com). But beyond corporate careers, the diverse economy means entrepreneurs, creatives, and healthcare workers will also find robust networks and employers here. Simply put, career opportunities abound. Unemployment in the Chicago metro area remains low relative to national averages, and with so many industries present, the city isn’t overly reliant on one sector. This stability and variety can be a big draw for ambitious young professionals ready to launch or advance their careers.

Additionally, Chicago’s central location is a perk for business and personal travel. Two major airports (O’Hare and Midway) make it easy to fly anywhere, and Chicago’s position as a Midwest transportation hub means many companies base their operations here for logistical convenience. Whether you’re looking to climb the corporate ladder or join a scrappy startup, Chicago offers a fertile ground for professional growth.

Big City Living at a (Relatively) Affordable Cost

Another compelling reason to choose Chicago is the cost of living, which is more manageable than in many other major cities. While Chicago is not “cheap” by any means, it is significantly more affordable than places like New York, San Francisco, or Los Angeles. For example, median rents in NYC and SF are almost double what you’d pay in Chicago (timeout.com). As of late 2023, the average rent in Chicago was around $2,250 per month, high but still well below the averages in coastal cities. In practical terms, your dollar stretches further here: you can often afford a larger or nicer apartment in Chicago on the same budget that would get you a tiny shoebox in Manhattan.

Housing aside, everyday expenses like groceries, restaurants, and entertainment also tend to cost less than in the priciest East or West Coast cities. Chicago even has some advantages, like reasonably priced public transit (a train ride is only $2.50) and Illinois’s flat income tax, which can benefit certain earners. Many newcomers find that Chicago offers big-city amenities without the bank-breaking budget. It’s one reason why new generations of renters are choosing Chicago for its high quality of life combined with lower living costs compared to other large U.S. cities (blog.aptamigo.com).

Of course, within Chicago, costs vary by neighborhood and lifestyle. Trendy downtown areas (River North, West Loop, etc.) command higher rents, while more residential neighborhoods or those farther from the center (like Rogers Park or Hyde Park) offer better deals. The good news is that you have options. If saving money is a priority, you can find reasonably priced areas or look for deals (insider tip: apartment rents tend to be cheaper in winter when demand is lower). Overall, Chicago lets you enjoy the excitement of a major metropolis at a comparatively lower cost – a huge plus for young professionals who want an urban adventure without wrecking their finances.

Related: The Best Luxury Apartments with Fitness Centers in Chicago

Incredible Food Scene and Nightlife

Chicago is famous for its food, and rightfully so. If you’re a foodie (or just love to eat), this city will spoil you with choices. Chicago’s dining scene ranges from down-to-earth delicious to internationally acclaimed. On one end, you have the iconic local staples: deep-dish pizza, Chicago-style hot dogs (no ketchup, of course), Italian beef sandwiches, and Garrett’s popcorn – must-try comfort foods that Chicagoans hold dear. On the other end, Chicago is home to world-class restaurants, including 26 Michelin-starred eateries and dozens of James Beard Award winners (chicago.gov). In total, there are over 7,300 restaurants in the city, representing cuisines from all over the world (chicago.gov). Whether you crave authentic Mexican tacos in Pilsen, spicy Indian curry on Devon Avenue, or a cutting-edge tasting menu in West Loop, you’ll find it here.

The late Anthony Bourdain once touted Chicago as the only U.S. city that can truly rival New York’s food culture – praise that locals echo. Chicago’s food scene goes far beyond pizza and hot dogs. You can slurp ramen in a hidden Chinatown noodle shop, savor Michelin-starred fine dining at Alinea, grab a famous Italian beef at the original Al’s Beef, or munch on gourmet donuts at a hip coffee shop. The variety and quality are astounding. Importantly, dining out in Chicago is often more affordable than in NYC or LA, so young professionals can enjoy the restaurant scene more frequently without breaking the bank. Plus, many neighborhoods have their own cluster of cool bars and eateries, so you don’t always have to go downtown for a great meal.

When it comes to nightlife, Chicago holds its own as well. The city has a thriving bar scene – from sleek cocktail lounges in the River North nightlife district to historic dive bars in Logan Square. You’ll find rooftop bars with skyline views, craft beer pubs (Chicago loves its beer – it boasts more breweries than any other US city), and famous blues and jazz clubs like The Green Mill. Music lovers will also appreciate the live music venues around town; on any given night you might catch an indie band at a Wicker Park club or a house music DJ set (Chicago is the birthplace of house music) at a downtown venue. And if you’re into dancing or late nights, many Chicago bars and clubs are open until 4 or 5 AM – the city has a legendary late-night scene. Simply put, you’ll never be bored after dark. From happy hour to the early hours of the morning, Chicago offers abundant entertainment and social life for young adults.

Rich Arts, Culture, and Entertainment

One of the best things about Chicago is the sheer amount of culture and entertainment it packs in. If you move here, you’ll have access to some of the nation’s top museums, theaters, and music venues. For art and history lovers, Chicago’s museums are world-class: the Art Institute of Chicago (home to famous works by Van Gogh, Picasso, and Monet), the Field Museum (where you can meet Sue, the largest T. rex fossil ever discovered), the Museum of Science and Industry, and many more. There’s always something new to learn or explore, and locals get perks like discounted admission days (timeout.com). The city also has a vibrant gallery scene and public art installations (don’t miss “The Bean” sculpture at Millennium Park).

If you enjoy theater and comedy, Chicago is a dream come true. This is the birthplace of improv comedy – legends like Tina Fey and Stephen Colbert got their start at The Second City theater here (timeout.com). You can catch hilarious improv and sketch comedy shows any night of the week. Chicago’s theater scene is second only to Broadway: big touring Broadway productions and homegrown plays run in the downtown Theater District, and there are hundreds of smaller theaters across the city producing everything from avant-garde plays to Shakespeare. In fact, Chicago has more than 200 theaters and 250 live music venues, illustrating just how abundant the arts are (chicago.gov). Love music? This city’s musical heritage runs deep (blues, jazz, gospel, rock – you name it). Major music festivals like Lollapalooza, Pitchfork, and Riot Fest take over the city in summer, and throughout the year, you can catch performances by the renowned Chicago Symphony Orchestra or see big-name concerts at venues like the United Center (timeout.com). No matter your cultural interest – be it opera or underground indie bands – Chicago will keep you entertained.

Sports are also a huge part of Chicago’s culture and pride. If you’re a sports fan, you’ll fit right in cheering for the Chicago Cubs or White Sox (yes, the city has two MLB teams!), the Bears (NFL), Bulls (NBA), Blackhawks (NHL), or the Chicago Fire (MLS). Few cities have as many major league teams as Chicago, and the local fan spirit is contagious. Wrigley Field, home of the Cubs, is an experience in itself – a charming, century-old ballpark nestled in a lively neighborhood. Even if you’re not a die-hard sports fan, attending a game at Wrigley or the United Center is a classic Chicago bucket list item and a fun way to spend a weekend.

The bottom line: Chicago is rich in culture and fun. From high art to pop culture, from museums by day to concerts by night, you’ll always have something to do. Many events are even free or low-cost – for instance, the city hosts 36 annual parades and 40+ film festivals, and you can often find free concerts or movies in the parks (chicago.gov). Living in Chicago means you’ll never run out of new experiences, and you’ll become part of a community that’s passionate about its food, arts, sports, and traditions.

Beautiful Parks, Lakefront, and Outdoor Activities

Despite its urban density, Chicago is also an outdoor lover’s city, especially in the warmer months. The city’s official motto is Urbs in Horto – Latin for “City in a Garden” – and Chicago works hard to live up to that name. There are over 600 parks spread throughout the neighborhoods (chicago.gov), ranging from tiny pocket parks to expansive green spaces. The crown jewel is Grant Park and adjacent Millennium Park downtown, where you’ll find gardens, public art, and open lawns hosting summer concerts and movie nights. Chicago’s park system includes everything from tennis courts and soccer fields to nature sanctuaries and playgrounds (chicago.gov), giving residents plenty of room to relax or play sports.

Perhaps the greatest outdoor asset is the Lake Michigan lakefront. Chicago sits beside one of North America’s Great Lakes, and the city has wisely preserved miles of lakefront for public use. Along the shoreline, you’ll find 29 beaches – yes, real sandy beaches in the city, which are packed with volleyball games, swimmers, and sunbathers in summer (chicago.gov). An 18-mile Lakefront Trail runs along the water, popular for jogging, biking, and strolling with breathtaking skyline views. On warm weekends, you might rent a bike or take a jog with the sparkling blue lake on one side and the city on the other. You can also kayak the Chicago River, go on boat cruises, or even join paddle-boarding sessions on the lake. In many ways, Chicago becomes a beach town in the summer, and it’s easy to forget you’re in the heart of a metropolis when you’re out on the water (timeout.com).

Chicago’s outdoor scene also shines through its festivals and community events. In spring and summer, nearly every neighborhood throws its own street festival – from art fairs and music fests to food events like the famous Taste of Chicago. These festivals often take over the streets with live bands, food vendors, and locals mingling (usually with a craft beer in hand). It’s a fantastic way to spend a weekend and meet people. The city officially hosts 74 music festivals and 36 parades each year, plus farmers’ markets, outdoor fitness classes, and more (chicago.gov). Even in winter, you’ll find outdoor fun like ice skating rinks at Millennium Park and the Lincoln Park Zoo’s holiday lights. If you value access to green space and year-round activities, Chicago offers the best of both worlds: a bustling city and ample outdoor beauty.

Reliable Public Transit and Easy City Navigation

One often-overlooked reason to love Chicago is how easy it is to get around without a car. The public transportation system here is one of the best in the country. The Chicago Transit Authority (CTA) runs an extensive network of buses and the famous elevated trains (the “L”). The CTA trains reach every corner of the city, from the downtown Loop out to far-flung neighborhoods. You can live in many parts of Chicago and reliably commute by train or bus to work, to school, or to meet friends. Trains run frequently and 24 hours on some lines, and a single ride is quite affordable compared to other cities (still just $2.50 per ride). Many young professionals in Chicago don’t bother owning a car – it’s easy to be a pedestrian or cyclist, and there are Divvy bike-share stations all over for convenient biking. Chicago is even ranked among the top U.S. cities for biking, with hundreds of miles of bike lanes and trails (chicago.gov).

If you do drive, Chicago’s traffic is manageable by big-city standards (though rush hour can be heavy). But the ability to live car-free is a major perk. You can save money on gas and parking, and enjoy a short commute by hopping on the L or bus. The city’s layout is a straightforward grid, which makes navigation intuitive whether you’re walking, biking, or driving. And for longer trips, the transit links are superb: besides the two airports, Chicago is a national rail hub (Amtrak trains radiate out from Union Station) and a highway hub as well. In short, Chicago is well-connected, both internally and to the rest of the world. Young professionals appreciate the freedom to explore the city easily – you can have brunch in one neighborhood, an afternoon museum visit in another, and dinner across town, all without needing a car.

Midwestern Friendliness and Community Spirit

Moving to a new city can be intimidating, but Chicago’s people and community spirit help make the transition easier. There’s a genuine pride among Chicagoans about their city – you’ll see the four-starred Chicago flag on hats, t-shirts, even tattooed on locals – and they tend to welcome newcomers who also love the city (timeout.com). Unlike some places where long-time residents can be aloof, Chicago generally embraces transplants (after all, many people here came from somewhere else too). You’ll find it natural to strike up conversations at a neighborhood street fest or while waiting for the train. Neighbors often get to know each other, and many communities have active neighborhood groups and events that you can join.

The city’s Midwestern mentality is frequently noted: Chicago sits at the crossroads of the country, embodying a bit of East Coast hustle with a dash of Midwest warmth. That means people are often polite, willing to help, and have a no-nonsense friendliness. Don’t be surprised if a stranger holds the door and says “have a great day,” or if a coworker invites you to their weekend BBQ soon after you’ve met. This welcoming culture can be a huge relief for young professionals moving alone or anyone worried about making friends in a new city. Plus, there are plenty of social opportunities – intramural sports leagues, volunteer organizations, professional networking events – where you can meet like-minded people and become part of the community.

Chicagoans also share a certain resilience and camaraderie, forged perhaps by those rough winters and passionate sports fandom. Come winter, you’ll see residents band together, whether it’s helping push a stranger’s car out of snow or simply commiserating over the cold at a local cafe. By summer, everyone’s in great spirits enjoying the city together. In summary, if you move to Chicago, you’re not just getting a place to live – you’re joining a lively community of people who love their city and will be happy to show you why.

Ready to Call Chicago Home?

In answering “Should I move to Chicago?”, consider the compelling reasons above. Chicago offers career opportunities, a comparatively affordable cost of living, amazing food and culture, fantastic public amenities like parks and transit, and a welcoming community vibe. It’s a city where you can advance your career during the day, enjoy deep-dish pizza and comedy shows at night, relax on the beach or in a park on the weekend, and build a network of great friends along the way. Of course, like any big city, Chicago has its challenges – winters can be harsh, and the cost of living is still higher than in smaller towns – but for many, the pros far outweigh the cons.

If you do decide to make the move, you won’t be alone. Thousands of young professionals move to Chicago each year for its unique mix of opportunity and livability. And when you’re ready, AptAmigo is here to help make your transition easy. AptAmigo’s local apartment experts can help you find the perfect Chicago apartment for free, matching you with the ideal neighborhood and building for your needs. Moving to Chicago is a big adventure, but with the right guidance, it can also be an exciting and smooth process. Good luck, and maybe soon you’ll be enjoying a Chicago-style hot dog while gazing at the skyline from your new hometown!

Up Next: Chicago Apartment Spotlight – Flora

FAQs