A recent grad’s weekend adventure in the Windy City — with side commentary for future Chicagoans.

Chicago. The name alone makes people think of deep-dish pizza, towering skyscrapers, a skyline that rivals NYC, and… if your news diet includes Fox, maybe a crime documentary. But let’s clear the air — this city is vibrant, dynamic, and full of charm. You just have to know where to go, what to skip, and how to vibe with it.

I just graduated and I’m about to move to Chicago full-time for a new job (yay adulthood!). But before the big move, I took a weekend trip to see the city for myself. Here’s how it went — and what I learned.

Is Chicago Safe?

Let’s get this out of the way. Yes, Chicago has crime. So do all major cities. But unless you’re actively trying to find trouble (like wandering into West Garfield Park at 2 a.m. with your AirPods in), you’re going to be fine. Stay alert, be street smart, and you’ll enjoy your weekend just like you would in NYC or LA.

If you’re worried, stay in more central or north side neighborhoods where you’ll find more foot traffic, lights, and, let’s be real, brunch spots.

I Stayed Near the Magnificent Mile — Was It Worth It?

Absolutely. It’s central, walkable, and pretty safe. You’re near:

• The Riverwalk (great for an afternoon stroll and killer skyline photos)

• Millennium Park (yes, the Bean — take the pic, move on)

• Navy Pier (skip it unless you have kids or love overpriced hot dogs)

Things To Do on a Budget (or Close To It)

🏙️ Day One: Classic & Cool

• Walk the Riverwalk

• Chicago Cultural Center – Gorgeous architecture and free exhibitions.

• Art Institute of Chicago – Not cheap, but worth it. Half-day here = soul food.

• Grab a slice at Lou Malnati’s (deep dish heaven)

🌆 Day Two: Neighborhood Hopping

• West Loop – Trendy, foodie paradise. Try Time Out Market.

• Logan Square – Indie shops, murals, local brews, and a cool crowd.

• Chinatown – Walk through the gate, eat at Joy Yee or MingHin, and stop for bubble tea.

• Catch sunset at Adler Planetarium’s lakeside view – One of the best skyline spots in the city.

Food Recs That Won’t Break the Bank

• Portillo’s – Chicago dogs and chocolate cake shake. Yes, you read that right.

• Parlor Pizza Bar (West Loop) – Affordable brunch/lunch, vibey patio.

• Xoco (by Rick Bayless) – Tortas and churros. Thank me later.

• Devil Dawgs – For late-night eats near DePaul.

• Chicago Diner (Lakeview) – Veg-friendly comfort food.

Thinking of Moving? Here’s the Vibe Check on Neighborhoods

💼 For Young Professionals:

• Old Town – Historic charm + great bars.

• South Loop – Skyscraper views, walkable, near museums.

• West Loop – Expensive but oh-so-Instagrammable.

• River North – Clubs, condos, and cocktail bars.

🎉 Nightlife Crowd:

• River North – Bottle service and bass drops.

• Wrigleyville – Drunk Cubs fans and post-grad chaos.

• Logan Square – Dive bars, vinyl, and irony.

• Boystown – Drag shows, rainbow crosswalks, and dancing.

👨‍👩‍👧‍👦 For Families:

• Lincoln Square

• North Center

• Edgewater

• Roscoe Village

✊🏾 For Culture, Diversity & Community:

• Bronzeville – Historic, artistic, full of Black-owned gems.

• Hyde Park – Obama’s old hood, University of Chicago, diverse and beautiful.

• Albany Park – Immigrant-rich and deliciously international.

• Andersonville – LGBTQ+-friendly and cozy.

• Pilsen – Murals, tacos, and indie flair.

😎 If You’re a Trendy Gentrifier:

• Logan Square

• Avondale

• Humboldt Park

• Bridgeport

😬 If You’re Too Trendy and Don’t Care About Fitting In:

• Little Village

• East Garfield Park

• South Shore

• (But seriously, be respectful. Gentrification is real.)

Where NOT to Live (Unless You’re Local or Know the Area Well)

Avoid moving into:

• Englewood

• Austin

• Roseland

• West Garfield Park …unless you have a strong reason or connection to the area. Safety and infrastructure vary widely here.

Final Thoughts

Chicago is layered. It’s not just deep-dish and skyscrapers. It’s jazz and jibaritos, lakeshore trails and late-night tamales. Two days isn’t nearly enough, but it was a start — and now I’m stoked to call it home.

If you’re visiting, come with an open mind, comfortable shoes, and an empty stomach. If you’re moving, think about what matters to you — nightlife, walkability, community, affordability — and you’ll find your perfect pocket of the city.

Got any favorite Chicago recs or hidden gems I should know about? Drop them in the comments 👇