Best Things To Do In Chicago

Let’s be real—Chicago can feel a little intimidating at first. You’ve got the skyscrapers, the lake, the deep-dish pizza debates. But once you spend a day here, it’s like that friend who’s loud but genuinely kind; they just want you to have a good time.

So, whether you’re visiting for a weekend or finally exploring your own backyard, here are the best things to do in Chicago. No tourist traps, just the stuff that makes you smile and say, “Okay, I get it now.”

Walk the Lakefront Trail (Even if You’re Not a Runner)

You don’t need a gym membership in Chicago. You just need the Lakefront Trail, a 18-mile ribbon of concrete that hugs Lake Michigan. It’s where you’ll see the guy in neon spandex pass a mom pushing a stroller while a dad tries to teach his kid to ride a bike.

I once sat on a bench near Navy Pier and watched a seagull steal a stranger’s sandwich. The stranger laughed. That’s the vibe here.

Pro tip: Bring a blanket and a cheap book. You don’t have to walk the whole thing; just find a patch of grass and pretend you’re on vacation.

Eat a Chicago Dog (Hold the Ketchup)

You can’t say you’ve done Chicago until you’ve had a dog from a shack with a neon sign. It’s a Vienna Beef frank on a poppy seed bun, loaded with yellow mustard, relish, onions, tomatoes, pickles, sport peppers, and a dash of celery salt.

No ketchup. Seriously. If you ask for ketchup, the person behind the counter might just sigh and then hand you a napkin anyway because Chicagoans are nice like that.

Try it at Portillo’s or a corner cart by the El tracks. It’s messy, perfect, and costs about the same as a fancy coffee.

See the City from the River (Not Just a Tour Boat)

I know, I know—everyone says take an architecture boat tour. But here’s the thing: they’re right. Even locals do this on sunny Saturdays because the guides are hilarious and the buildings actually look like they’re showing off.

If you’re on a budget, grab a drink from a nearby café and sit on the riverwalk stairs. Watch the boats go by, and you’ll hear a dozen languages in ten minutes.

One evening I saw a guy propose on a rented kayak. The ring box fell in the water. The bride-to-be laughed so hard she almost tipped over. That’s Chicago romance.

Get Lost in a Neighborhood (Not Downtown)

Downtown is shiny and clean, but the real Chicago lives in neighborhoods like Wicker Park, Pilsen, or Logan Square. Walk down a street and you’ll find a bookstore run by a retired librarian, a taco joint with a line out the door, and a mural of a cat wearing sunglasses.

In Pilsen, every alley is a gallery. The street art here tells stories about family, struggle, and pure joy. Bring your phone for photos, but also just look up for a while.

My favorite memory? Sitting on a stranger’s front porch steps in Logan Square, eating an empanada, and waving at a dog in a passing car. The dog waved back with his paw.

Visit the Art Institute (But Only the Weird Parts)

You don’t have to be an art snob to love the Art Institute. Skip the Monets if they bore you—head straight for the Thorne Miniature Rooms, tiny dollhouse-sized rooms from different eras. They’re weirdly addictive.

Or find the American Gothic painting and take a selfie making the same grumpy face. The guards have seen it all and they’ll smirk politely.

If you’re low on time, just spend 20 minutes in the modern wing. There’s a giant red sculpture that looks like a paperclip on steroids. Kids love it. So will you.

Eat a Deep-Dish Pizza Like a Local

Deep-dish is not a pizza—it’s a casserole you eat with a fork. And that’s why it’s amazing. Go to Pequod’s for the burnt cheese crust or Gino’s East if you want to write your name on the walls.

Here’s the secret: you order a medium deep-dish for two people, then you eat one slice and wonder what you’ve done with your life. The leftovers are even better cold the next morning.

One time, I brought a deep-dish to a potluck and the host cried. Not exaggerating. Chicago pizza is that powerful.

Ride the L Train Like You Own It

The “El” is not a subway—it’s a squeaky roller coaster that rattles through alleys and backyards. You’ll see laundry hanging from windows and catch a glimpse of someone’s living room where they’re watching the same show you are.

Hop on the Brown Line at rush hour and pretend you’re in a music video. The lights flicker, the doors groan, and somebody’s always playing a saxophone at the platform.

If you’re lucky, you’ll get a car full of strangers laughing together when the train stops unexpectedly. It happens. We just deal.

Watch the Skyline at Sunset

For the best free show, go to the Adler Planetarium steps after 7 p.m. The city lights up like a million fireflies, and the lake turns pink and orange. You’ll see couples hugging, friends taking bad group photos, and at least one person playing a guitar.

Bring a thermos of hot chocolate in winter or a can of soda in summer. Sit there for ten minutes without looking at your phone.

I did this last fall, and a kid next to me said, “It looks like the buildings are on fire but in a nice way.” Kids get it. And so will you.

Grab a Drink at a Dive Bar

Forget the rooftop rooftop bars with $20 cocktails. Find a place with sticky floors and a pinball machine. Try The Maple Leaf in Lincoln Park or The Owl in Bucktown.

You’ll meet a guy who’s been drinking the same beer since 1998 and a bartender who calls you “hon.” It’s warm, it’s cheap, and the jukebox plays Tom Petty on a loop.

One night I watched two strangers bond over a broken pool table. By the end, they were exchanging numbers. That’s Chicago for you—unpolished, totally unexpected, and full of heart.