The first time I arrived in Chicago, I didn’t know if I was moving into a city or a movie set. Between the iconic skyline, the deep-dish debates and the shockingly windy lakefront (yes, the nickname is well-earned), I was immediately aware I wasn’t in the Midwest suburbs anymore.
If you’re thinking of living and working in Chicago, especially as a first-time visitor, it’s an experience full of charm, challenge and more than a few surprises, so let’s talk about what it’s really like to show up here with only your suitcase and your dreams.
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Starting With What You Know
Let’s not overcomplicate things. If you’re new to the city, you probably want to work while you figure the rest out, so hospitality gigs will become your best friend. Chicago is packed with coffee shops, bakeries and specialty cafés, and barista work is a solid entry point.
In fact, that’s how I landed on my feet. If you’re in the same boat, start your search here: Café jobs in Chicago – Barista needed. This is your ticket to a whole new city. If you can steam milk and handle small talk before 9 a.m., you’re already winning. Now onto the slightly more complicated part.
Cost of Living
Chicago isn’t cheap. You might not be hemorrhaging cash like you would in Manhattan, but you’ll still feel the pressure, especially when it comes to housing.
According to RentCafe, the cost of living in Chicago is about 15% higher than the national average. The average monthly rent sits around $2,381, and buying a home is a pipe dream for many first-timers, with prices averaging over half a million bucks.
That said, costs can be manageable if you know where to look. Roommate situations are common (Facebook groups and Reddit threads are goldmines), and public transit can help you skip the expense of owning a car if you’re okay with a few quirky delays.
Getting Around
The “L” train is short for “elevated,” but sometimes also “elusive.” If you’ve never relied on public transport before, this will be a learning curve.
Jokes aside, Chicago’s CTA system is actually one of the more reliable ones in the country, especially if you live near one of the main lines like the Red, Blue or Brown. The city is very walkable, too. And if all else fails, you can always hop on a Divvy bike.
My advice is to get a Ventra card early. It’ll save you time and sanity. Also, keep a mental note of which stops are shady at night. Just because the city has charm doesn’t mean you should let your guard down entirely.
Work Culture
Chicago strikes an interesting balance. People here work hard, but there’s also a refreshingly honest attitude about life outside of work. It’s not all side hustles and “rise and grind” nonsense. You’re just as likely to meet someone who clocks out and heads to a rec soccer league as someone who’s building a startup on the side.
That said, if you’re in hospitality or retail, be ready to hustle. Service standards are high, but Chicagoans tip decently, smile often and tend to appreciate good service. There’s a sense of shared struggle here that makes it easier to deal with being short-staffed on a Cubs game day.
Finding Your Crowd
Chicago is famously neighborhood-based, and the vibe shifts dramatically from one area to another.
Logan Square leans artsy and edgy, Lincoln Park is full of recent grads and stroller squads and Wicker Park sometimes feels like a living Pinterest board. If you’re trying to find your people, go where your interests take you. It’s that kind of town.
If you’re a bookworm like me, you’ll know that Chicago is the backdrop for a surprising number of dystopian tales and dramatic story arcs. One of my favorites is the relationship between Tris and Four in the Divergent series.
Set in a crumbling, faction-driven version of the city, their story adds a kind of haunting poetry to familiar spots like the Sears (ahem, Willis) Tower and Navy Pier. This piece on star-crossed lovers highlights that dynamic and reminded me that this city has long been a muse for storytellers.
It’s strange but kind of lovely to walk through downtown and imagine the skyline as part of a post-apocalyptic YA novel.
Weather
The winters here are rough. The wind cuts through your coat, your jeans and your soul. But the summers make it all worth it. Rooftop bars open up, and the lakefront turns into the city’s unofficial gym, beach and hangout spot. Plus, the sunsets over Lake Michigan are my actual therapy.
If you survive your first Chicago winter without crying into a space heater, congrats; you have something special to look forward to.
Final Thoughts
Chicago will be a vibe shift for most people. It teaches you resilience, rewards curiosity and gives you a solid story to tell. There’s something strangely empowering about this place.
It’s the kind of city that doesn’t pretend to be easy, but it’s always worth it. You show up, get your bearings, take a few punches from the wind, and before you know it, you realize you belong.
Ross, an exam specialist with a passion for education, writes comprehensive articles on exam results and admit cards. His expertise ensures students receive reliable information and useful tips to excel in their exams.
