If you’re thinking about making a move to Chicago for the first time, you’ve probably already heard a ton of opinions from friends, family, and YouTube videos (and we hope you checked out Ben’s YouTube channel as well).
We’re the Ben Lalez Team, and after helping over a thousand families find their perfect Chicago homes over the last decade, we’ve heard everything there is to know about the Windy City.
Today, we’re sharing an honest look at what makes Chicago an amazing place to call home, and what might make you think twice. There won’t be any sugar-coating here. Just real talk from locals who know this city inside and out.
Let’s get into our top 5 reasons to make the move, and the top 5 reasons why you might want to reconsider.
5 Reasons To Move To Chicago
1. A Neighborhood For Every Personality
Chicago isn’t just one city. It’s more fondly known for it’s 77 neighborhoods, and each one has its own character and community vibe.
For example, in River North you can feel the hustle and bustle, and in Lincoln Park you’ll enjoy the tree-lined streets. If you have an artistic spirit, give Wicker Park a visit. And if you’re a lakefront type of person, then Lakeview is the spot you want to check out.
Each neighborhood gives you a different experience, which means that with a little bit of research and exploration, you can find exactly what fits your lifestyle. We promise there’s a perfect Chicago neighborhood waiting for you.
2. World-Class Culture But Still Affordable
Chicago is a cultural powerhouse. You’ll find renowned museums like the Art Institute and Field Museum and an incredible theater scene. If you’re a music lover, there are music venues that host everything from jazz and blues to all of your favorite concerts.
Are you a foodie? Because you’ll find a world-class food scene in the city, from small and intimate diners to Michelin-starred restaurants. And if you love outdoor events, Chicago is a city of festivals. There are charming neighborhood street fests, and massive events like Lollapalooza and the Chicago Jazz Festival. Whichever types of festivals you like attending, Chicago has them all.
The best part is that you can enjoy all this at a fraction of the cost of New York or Los Angeles.
3. Real Estate Prices That Give You More For Your Dollar
When it comes to housing affordability, your budget stretches much further in Chicago than in other major cities around the U.S.
The average median home price in Chicago is around $355,000. Compare that to nearly $750,000 in Boston and over $970,000 in Los Angeles, and you’ll get a better sense of just how affordable Chicago can be. This means with the same budget, you can get more space, better finishes, and maybe even that yard you’ve been dreaming about.
The real estate market in Chicago is also incredibly diverse, offering all kinds of property types. From historic bungalows and classic greystones to modern condos and converted lofts, there are plenty of fantastic options for everyone.
4. Getting Around Is Convenient
One of Chicago’s best features is its public transportation system. The “L” trains and vast bus network make it easy to get around the city without owning a car.
The city’s grid system makes the system easy to figure out, and most neighborhoods are highly walkable. During the warmer months, the lakefront trail and growing network of bike lanes make cycling a great option too.
If you’re planning a weekend road trip, Chicago is close to lots of nearby towns. You have access to beautiful state parks and even neighboring big cities that are all within a few hours’ drive. You won’t have to drive further than a couple of hours if you want to explore more of what the Midwest has to offer.
5. Four Seasons Of Fun
Yes, Chicago winters are famous (more on that later), but having four distinct seasons means four climates where you can enjoy different activities.
In the summer, you can enjoy 26 miles of lakefront, outdoor dining, and parks filled with free concerts and movies. In the fall, you’ll get gorgeous autumn colors and crisp sweater weather to take some of your best Instagram photos. Winter has its own charm with ice skating and holiday markets. And of course, spring is when we all celebrate that winter has finally passed!
5 Reasons To Think Twice About Moving To Chicago
1. Winter Is A Big Drag
We need to talk about winter. Chicago’s winters aren’t just cold. They’re an entire lifestyle adjustment.
December through March means you’ll be dealing with freezing temperatures and lakefront winds that cut right through your bones. It takes a special kind of mental toughness to handle the wind chill when it hits negative numbers.
Daily life gets more inconvenient in the winter. You’ll have to deal with warming up your car, snow-covered sidewalks, and the infamous “dibs” system for parking spaces. Want to learn more about what dibs are, along with other surprising facts about life in Chicago for first-timers?
Winter is not for everyone, but it’s manageable. If you’re a person who deals with seasonal depression, winter in Chicago can seem like it drags on forever.
2. Higher Property Taxes
One thing that surprises a lot of people is that Chicago’s property taxes are significantly higher than the national average.
In Cook County, the effective tax rate is about 2% of your home’s value. That means on a $300,000 home, you’d be paying roughly $6,000 a year in property taxes. That’s essentially double the national average and much higher than what you’d pay in many other cities. We’ve written before about how to calculate your Chicago property taxes, so make sure to check out that article.
The property tax system in Chicago can be complicated, with various exemptions that can help save you some money if you know how to find them and use them. And because reassessments happen every three years, your tax bill can change significantly over time.
3. Big City Problems
Like any major city, Chicago has its big city challenges. Traffic can be pretty terrible during rush hours. Finding parking in popular neighborhoods might have you questioning your life choices. Commuting in a car can definitely test your patience.
You’ll find crime in some areas, but it varies depending on the neighborhood. We’re a big city, so some parts feel completely different from others when it comes to safety and city services.
Dealing with the city can be frustrating sometimes too. Getting permits for home improvements and dealing with Chicago-specific regulations will take time and preparation.
4. The Cost Of City Living Adds Up
Although Chicago is more affordable than other coastal cities, it’s still pricier than many other cities in the Midwest. Aside from housing costs, there are other expenses to consider.
Chicago’s sales tax is among the highest in the country at 10.25%. You’ll also find car insurance rates much higher than the national average.
If you’re buying a condo, you’ll have to pay HOA fees and that adds to your monthly housing costs.
And if you own a car, city stickers, parking permits, and occasional parking tickets is something you’ll have to deal with regularly.
5. It Takes Time To Really Feel At Home In Chicago
Feeling like a true Chicagoan will take you some time. The city has its own way of doing things and its own language. For example, we never call it the subway, we call it “The L.”
If you’re trying to meet people and build up a circle of friends, it can be tough, especially if you’re moving from a smaller community. Chicago neighborhoods can sometimes feel like separate towns with their own community cultures and vibes. This is just normal in big city life.
This also means that it takes time to really get to know your way around and find your favorite spots. And figuring out which neighborhood truly fits your lifestyle might involve some trial and error, but you’ll have fun exploring.
The Bottom Line
Chicago really has a lot to offer.
While it might not be for everyone, the city offers both big-city amenities and Midwestern friendliness with its own character. It is something that will definitely grow on you.
We recommend coming in with realistic expectations. Understand the challenges, but also look for the amazing opportunities that come with living in Chicago.
Try talking to people who live here. And if possible, visit Chicago at different times of the year and explore all the different neighborhoods before making your decision.
Whether you decide Chicago is right for you or not, we’re always happy to grab a coffee with you and share our insights. Contact us if you’d like to learn more about specific neighborhoods, or what it’s really like to live here.
The best decisions are informed ones, and we’re here to help you figure out if Chicago should be your next home!
