Ah yes, Chicago. The City of Big Shoulders. The Jewel of the Midwest. The Windy City. No matter what you call it, Chicago is a true American city with a storied past and a promising future. But is it your kind of town?
If you’re considering packing up your life and heading to the City that Works, it’s time to ask yourself if the city will work for you. With that in mind, this Chicagoan has some words of advice for you, aspiring Windy Citizen.
1. Yes, the winters are cold. No one cares.
Many people, visitors and residents alike, talk about Chicago’s winters like they’re a frozen hell on earth. But they’re simply a fact of life here. Yes, you’ll want to get a good winter coat and a solid pair of waterproof boots to get you through the cold months, but the city’s frozen days have a way of making you even more appreciate of what comes next.
2. The summers make the frostbite worth it.
By the time you’ve fully thawed from the polar vortex, summer in Chicago will quickly make you forget all that. The weather is glorious and you’ll find yourself soaking up every possible moment in it, whether that’s lazing about at the beach, reading in a park or throwing back a beverage on a patio.
3. Chicagoans love the outdoors.
Even though the city doesn’t have an oceanfront or much terrain to speak of, it’s easy to take in nature’s beauty at the city’s many parks, conservatories, nature preserves and a gorgeous river.
4. The lake will become your best friend.
Who needs an ocean when you’ve got this thing? The lakefront offers many miles of beaches and a massive biking and running trail that outdoorsy types will flock to. And the backdrop of the city’s iconic skyline isn’t so bad either. It’s the sort of view that takes the breath away from even the most jaded Chicagoan.
5. We take our grub seriously.
We’re not just talking about deep dish and hot dogs, here. Chicago is brimming with some of the most phenomenal food in the world, an eclectic mix of fare that reflects the city’s diverse population. From four-star dining to greasy-spoon excellence, carnivore fantasies to vegan decadence, if you can dream it up, you can get it in Chicago.
6. You’ll want to live by a grocery store.
That said, proximity to a grocery store is important. With seemingly endless restaurant options, it can be easy to spend your whole paycheck on delivery, so you’ll want to make it as easy as possible to keep your fridge stocked, though apps like Instacart are making life easier for Chicagoans lacking in grocery access.
7. Yes, Chicago is a big sports town.
Remember Bill Swerski’s Super Fans? The recent success of the Blackhawks and Cubs can definitely make it feel like the entire city is just as sports-obsessed as the iconic “SNL” sketch indicated. This is a city that gets behind its sports teams. But if rooting for the Bears isn’t your ticket, the city has a lot more to offer you.
8. It’s a serious music town, too.
Chicago is also a music lover’s dream come true. The birthplace of the blues and some of the best house, rap, gospel and alternative music ever made, the city continues to breed promising new talent. Better yet, there are concert venues, featuring local and international stars alike, around every corner and some of the nation’s best music festivals take place here each summer. Get ready to host your college friends visiting from out of town!
9. …And a comedy town.
A laundry list of comedy’s biggest names — Bill Murray, Dan Aykroyd, Gilda Radner, Amy Poehler and Tina Fey got their start on the main stage of Chicago’s Second City. The next generation of funny men and women continue to rise through the ranks here at the city’s many options for improv, sketch and standup comedy.
10. …And an art town.
Home to one of the world’s most revered art museums, the Art Institute of Chicago, the art doesn’t stop there. Areas like Pilsen are known for their beautiful murals while galleries throughout the city showcase the budding talent of local artists. On top of that, companies like the Joffrey Balley and the Lyric Opera make it easy to take in world-class performing arts in town as well.
11. …And a theater town.
Thanks to incredible companies like Steppenwolf, the Hypocrites and many others, some of the nation’s best theater is born in Chicago. In fact, some have even called it the theater capital of America. Check out the storefront scene, which has very affordable ticket prices.
12. The architecture.
There’s a good reason that the Chicago Architecture Foundation’s boat tour is probably the only tourist activity locals will openly admit to actually enjoying: This city is home to an overwhelming number of stunning skyscrapers, churches and libraries dreamed up by some of the world’s best architects.
13. Ditch your car.
Seriously, Chicago’s trains and buses are your best friend and are pretty cheap and relatively widespread, especially if you’re living on the north side of the city. Between public transit, the city’s improved bike-lane strategy, bike-sharing, car-sharing and Ubers-a-plenty, Chicago has more than enough ways to get around.
14. If not, get ready to pay.
If you do decide to bring a car, you’ll want to mentally prepare for the stressors that come with it — traffic jams on the expressways, nearly constant fear of parking tickets and overzealous tow companies, sometimes-unpredictable street sweeping schedules and — thanks, winter! — digging it out when it snows.
15. It’s a renter’s city.
The price of buying within city limits can be pretty high, so you’ll definitely want to rent, at least at first. If you’re younger, you may want to live with a roommate, especially someone you already know or a friend-of-a-friend. If you’re short on time or coming from out of town, using an apartment-hunting service like Apartment People or Chicago Apartment Finders can be a huge time-saver — and they’ll be able to find you those hidden housing gems that fit your vibe.
16. This is a city of neighborhoods. Live in one.
Even without a car, you don’t need to live super close to where you work — and few Chicagoans do. A bit of a commute on the train can provide a nice chance to decompress from the day, reading a book or finally beating that next level of Candy Crush. And living in a neighborhood different from the one you work in helps you get away the daily grind and recharge. And, If you’re curious about the size of Chicago compared with other places in the world, check out this infographic.
17. Our neighborhoods are all distinctly unique.
Into sports and beer gardens? You’d love Lakeview or Lincoln Park. Love live music and dive bars? Ukrainian Village or Logan Square is for you. An aspiring foodie? You’d better check out the Near West Side. With 77 different officially designated community areas and various sub-neighborhoods within each of those areas, Chicago has something for everyone. To figure out what area will work for you, the Internet is your friend — use resources like DNAinfo’s neighborhood news pages, EveryBlock and Yelp to narrow down your options.
18. No, you won’t get shot.
Though headlines often focus on Chicago gun violence, most areas of the city are safer than they ever have been. Crime is a part of life in any city, of course, but the national news stories don’t tell the whole story. This is a city where you’ll get to know your neighbors.
19. You’ll never be bored.
Any given day in the city is packed with endless events and activities, many of them cheap or free. If you keep a close eye on event listings from Time Out and the Reader, you’ll soon have a calendar that’s overflowing with adventures. It just doesn’t get better than the free summer concerts at Millennium Park.
20. Before long, you’ll be one of us.
Unless you call it “Chitown.” Nobody says that.
We’re a pretty welcoming city. It doesn’t take very long to feel the love. Odds are you’ll be downing malort shots, complaining about City Hall politics and getting your tattoo of the Chicago flag like a local in no time. This is a city to be proud of.
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