The Things to Do in Chicago I Loved on My First Visit

I had always heard about the endless list of things to do in Chicago, but it wasn’t until I stepped off the train at Union Station that the city’s energy really hit me.

The rhythm of footsteps, the sound of street performers echoing through the underground tunnels, and the sharp contrast of towering skyscrapers against the expanse of Lake Michigan—it all felt bigger and bolder than I expected.

As someone who’s spent years crisscrossing cities across Europe, Asia, and South America, I thought I had a grasp on what a major urban center could feel like. Yet Chicago managed to surprise me.

Within hours of arriving, I found myself standing beneath Cloud Gate in Millennium Park, joining dozens of strangers marveling at our distorted reflections. That was the moment I realized this wasn’t just another stop on my travel list—it was the start of a personal relationship with a city that wears its character on every street corner.

For a first-time visitor, figuring out the best things to do in Chicago can feel overwhelming. There’s the pull of world-class museums, the lure of deep dish pizza, the draw of Lake Michigan’s breezy waterfront.

And then there are the unexpected discoveries: a neighborhood café tucked in the Fulton Market district, or stumbling across ART on THE MART projected onto the riverfront buildings at night. My first trip was a mix of both—the classics I couldn’t miss, and the quieter moments that gave me a glimpse into the city’s heart.

Looking back, I can say with certainty that the things to do in Chicago aren’t just about ticking off attractions. They’re about experiencing the pulse of the city—the blend of cultures, the pride of locals, and the way the city balances global recognition with a deeply rooted Midwest soul.

And that’s exactly what I want to share here: the highlights, the hidden gems, and the personal moments that made me fall for this place.

Why Chicago Captured My Heart Right Away?

What struck me almost instantly was the city’s architecture. Walking through the Chicago Loop, the skyline felt like an outdoor museum—French Baroque facades alongside modern glass towers, each building with its own story. Standing along the Chicago River and gazing up, I couldn’t help but think of the city’s resilience after the Great Fire, and how that tragedy reshaped it into one of the world’s great architectural capitals.

And then there’s Lake Michigan. Coming from New York City, I thought I understood waterfront living, but this was different. The lake felt endless, more like an ocean than a city backdrop. Locals jogging along the Lakefront Trail or families gathering at Maggie Daley Park gave it a neighborhood feel, even though it stretched as far as I could see.

But what really got me was the warmth of the people. Midwestern friendliness is not a myth. I lost count of how many times strangers offered directions or suggested their favorite pizza spot without hesitation. Those casual encounters—whether in a line at Lou Malnati’s or while renting a Divvy Bike Share—added layers of connection that I didn’t expect in a city this size.

What surprised me most? The balance. Chicago has the scale and energy of New York but without the constant rush. It felt more approachable, more livable. And for a traveler like me, used to finding edges of chaos in big cities, this balance was refreshing.

The Top Things to Do in Chicago (My Favorites)

1. Millennium Park & Cloud Gate (“The Bean”)

No matter how many times you’ve seen it in photos, nothing prepares you for standing in front of Cloud Gate. On my first morning in Chicago, I wandered into Millennium Park just as the sun was rising, and the reflective surface turned the skyline into a surreal painting.

I snapped the obligatory selfie, but then I stayed. I watched as locals on their morning jog paused to stretch nearby and tourists clustered under the mirrored arch. It felt communal—like everyone was part of this massive reflective artwork.

Millennium Park itself deserves attention too. The open lawns host concerts, and Buckingham Fountain nearby is a spectacle at night. For a free attraction, it’s hard to beat the value. If you go in December, the park transforms into a winter wonderland with ice skating—one of those fun things to do in Chicago that makes you feel like a local, even if it’s your first visit.

Insider tip: Arrive early in the morning or later in the evening. That’s when you’ll avoid the thickest crowds and get those dreamy reflection shots with fewer people in the frame.

2. Art Institute of Chicago

The Art Institute isn’t just a museum—it’s an experience. I spent nearly half a day here, and it still wasn’t enough. Walking through galleries that hold Monet’s “Water Lilies,” Hopper’s “Nighthawks,” and Grant Wood’s “American Gothic” was like flipping through the pages of an art history book, except I was standing inches away.

What hit me hardest was Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte.” I’d studied it in school, but seeing it in person—thousands of precise dots forming a whole scene—was breathtaking. The atmosphere inside the museum was contemplative, almost reverent, but not intimidating.

Practical advice: The museum is part of the Museum Campus and is included in the Chicago CityPASS and Chicago C3® tickets, which save money if you’re hitting multiple attractions. For anyone traveling with kids or couples looking for unique things to do in Chicago, the interactive exhibits make it enjoyable across all ages.

3. Navy Pier

I visited Navy Pier on a crisp evening, and it felt like Chicago was showing off. Families strolled by with popcorn, couples leaned against the railing to watch boats glide along Lake Michigan, and kids squealed with delight as the Centennial Wheel lit up against the twilight.

I couldn’t resist taking a ride myself, and the view—Chicago’s skyline glittering on one side, the endless stretch of water on the other—was one of those unforgettable fun things to do in Chicago that instantly made me feel connected to the city.

Navy Pier is more than an amusement stop. It’s a hub for entertainment with the Chicago Shakespeare Theater, fireworks shows in summer, and plenty of dining spots (I grabbed a slice of Lou Malnati’s deep dish here too). In December, the pier transforms into a holiday wonderland with Winter WonderFest, which made me think how perfect it is for families looking for things to do in Chicago with kids.

Tip: Go in the evening. The energy is livelier, the lights are spectacular, and the skyline reflections on the lake are breathtaking.

4. Chicago Riverwalk

The Chicago Riverwalk quickly became one of my favorite discoveries. By day, it’s a buzzing promenade with cafés, kayakers paddling under historic bridges, and locals enjoying a waterside lunch. By night, it transforms into something even cooler. ART on THE MART—the massive digital art projection on the Merchandise Mart—turns the riverfront into an open-air gallery.

I spent one evening just strolling, hopping between small wine bars and watching water taxis zip past. It’s the kind of place where you can simply sit, people-watch, and soak up the city’s rhythm.

For me, it was also the best way to understand Chicago’s architecture, with iconic structures like the Marina City towers and the French Baroque–inspired Wrigley Building looming overhead.

Insider reflection: This was the moment I stopped feeling like a tourist. Sitting by the river, latte in hand, chatting with a local about her favorite Chicago festivals—it felt like I’d slipped into the everyday flow of the city. For couples, this stroll easily counts as one of the most romantic things to do in Chicago at night.

5. Architecture River Cruise

If I had to pick just one experience to recommend, this would be it. The architecture river cruise wasn’t just sightseeing—it was storytelling. As we drifted along the Chicago River, guides shared tales of how the city rebuilt itself after the Great Fire, how the Willis Tower and John Hancock Center reshaped the skyline, and how neighborhoods like the Chicago Loop grew around these modern marvels.

I’ve admired skylines in cities like Shanghai and Dubai, but Chicago’s felt different—it was layered with history, pride, and creativity. Listening to the guide point out the details of Art Deco facades and modern glass towers gave me a deeper respect for the city. I learned that even public works like the bridges are celebrated feats of engineering.

Practical info: Cruises run most of the year, with summer offering the most comfortable rides. I took mine at sunset, and it was perfect—the golden light bouncing off buildings, the skyline slowly glowing as night fell. Whether you’re into history, photography, or just want one of the top 10 things to do in Chicago, this is the experience you shouldn’t skip.

6. Willis Tower Skydeck (The Ledge)

Standing 1,353 feet above the ground on the glass ledge of the Willis Tower Skydeck was easily one of the most adrenaline-pumping things to do in Chicago. My palms were sweating, my knees wobbled, and yet—I couldn’t stop smiling. The glass boxes extend four feet out from the building, so when you look down, it feels like you’re floating above the Chicago Loop.

It’s a unique experience, one that gave me a whole new perspective on the city. The view stretches across four states on a clear day, and seeing the grid of streets from above made me realize just how vast Chicago really is. For young adults or thrill-seekers, this is one of those fun things to do in Chicago that you’ll remember long after you’ve left.

Traveler’s tip: Visit close to sunset. Watching the city shift from golden hour into a twinkling sea of lights was unforgettable. If you’re planning your trip, note that Skydeck Chicago is included in Chicago CityPASS tickets, so you can save if you’re hitting multiple attractions.

7. 360 Chicago Observation Deck

While Willis Tower gives you the height, 360 Chicago offers something even more interactive—the Tilt attraction. Leaning out over the edge of the John Hancock Center with Lake Michigan stretching endlessly in the distance? Terrifying and exhilarating all at once. I’ve done observation decks around the world, but Tilt was one of the coolest and most unique things to do in Chicago.

The deck itself also has a more relaxed vibe than Skydeck. There’s a bar, so I grabbed a drink and just soaked in the views. Watching boats trail across Lake Michigan while spotting landmarks like Navy Pier, Wrigley Field, and even Millennium Park gave me a deeper sense of orientation in the city.

Insider comparison: If you only have time for one, Skydeck Chicago gives you the iconic Ledge experience, while 360 Chicago feels more atmospheric and fun—especially at night. Couples looking for things to do in Chicago tonight will appreciate the romantic glow of the city lights here.

8. Magnificent Mile

Even if shopping isn’t your thing, strolling the Magnificent Mile is a must. This stretch of Michigan Avenue is lined with high-end boutiques, flagship stores, and iconic architecture.

I wandered in and out of shops but found myself more fascinated by the buildings themselves—like the historic Tribune Tower and the neo-Gothic Wrigley Building.

Window-shopping here is as entertaining as people-watching. I grabbed a coffee from the Starbucks Reserve Roastery (which is worth a stop on its own) and just wandered.

Street performers added a soundtrack to the evening, while the city’s energy pulsed around me. It reminded me of Fifth Avenue in New York City, but with a Midwestern charm that felt more approachable.

Tip for travelers: If you’re visiting during the holidays, the Magnificent Mile Lights Festival in November is magical—one of the best things to do in Chicago in December. Families, couples, and solo travelers alike will find this area buzzing with festive spirit.

9. Chicago Theatre

I’ll never forget walking up to the Chicago Theatre at night. That iconic marquee, glowing against the dark sky, was a vision I’d seen in countless photos—and suddenly, there it was, right in front of me. I didn’t catch a full show, but I joined a guided tour and learned about its French Baroque interior, history of performances, and the role it plays in the city’s cultural identity.

Inside, the chandeliers and grand staircases felt like stepping back in time. The Chicago Theatre is more than just a performance venue—it’s a landmark that embodies the city’s love for the arts. For travelers searching for things to do in Chicago for adults or unique cultural experiences, catching a concert or comedy show here is perfect.

Personal note: Even if you don’t have time for a performance, seeing the marquee lit up is one of the top things to do in Chicago tonight. It’s one of those images that stays with you, long after your trip.

10. Lincoln Park & Zoo

After the buzz of downtown, I needed a breather, and Lincoln Park was exactly that. This massive green space stretches along Lake Michigan, and at its heart is the Lincoln Park Zoo—one of the best free things to do in Chicago today. I spent a morning wandering tree-lined paths, watching kids giggle at penguins and families picnic under the skyline.

What makes it special is the contrast. You’re standing in front of a lion enclosure, and just beyond it, you see the city’s towers rising in the distance. It’s a surreal blend of nature and urban life.

For couples, there are quiet gardens that feel romantic, while parents will find it a godsend when looking for things to do in Chicago with kids without spending extra.

Traveler’s tip: Combine your visit with a stroll to North Avenue Beach nearby. The view of the skyline from the sand is one of the most photographed spots in the city—and honestly, it’s even better in person.

11. Museum of Science and Industry

If you love interactive museums, the Griffin Museum of Science and Industry will blow you away. I went in thinking I’d spend an hour or two, but I ended up staying nearly half a day. The exhibits range from a real German U-505 submarine to a recreated coal mine, to a tornado simulation that actually lets you step inside swirling winds.

For me, the standout was the aviation wing. Standing under a World War II–era plane reminded me of why I travel—those moments where history feels tangible. It’s one of those fun things to do in Chicago for young adults, but I saw kids completely absorbed here too, proving it’s a hit across all ages.

Practical note: It’s located in Jackson Park, a bit south of downtown, so plan transport (CTA bus or rideshare). Entry can be pricey, but it’s included in the Chicago CityPASS. If you’re short on time, prioritize the submarine—it’s unforgettable.

12. Field Museum

Walking into the Field Museum of Natural History is like stepping into another world. The first thing you see is SUE the T. rex—towering and ferocious, but somehow welcoming too. I’d seen photos, but standing in the same hall as SUE felt monumental.

Beyond the dinosaurs, the museum houses Máximo the Titanosaur, ancient Egyptian artifacts, and cultural exhibits from around the globe. As someone who has visited museums from Paris to Mexico City, I was genuinely impressed by the depth here. If you’re building a list of the top things to do in Chicago, this deserves a spot near the top.

Insider reflection: I found myself drawn to the Native American collections, which offered a respectful and moving look at cultures often overlooked in other museums. Families will love it, but adults with an appreciation for history will find plenty of quiet corners to explore too.

13. Shedd Aquarium

There are aquariums, and then there’s Shedd. I walked in expecting tanks and fish—and walked out feeling like I’d traveled across oceans. From beluga whales gliding gracefully to colorful coral reef displays, the experience made me feel like a kid again.

One highlight was watching the penguins waddle across their exhibit, playful and curious. It reminded me how Chicago manages to offer world-class cultural spots while still making them accessible and fun. For parents, this is one of the best things to do in Chicago with kids, but I’ll be honest—I went solo and had a blast.

Pro tip: Pair your Shedd visit with a walk along the Museum Campus, where you’ll get unbeatable views of the skyline framed by Lake Michigan. If you’re visiting in summer, try to catch an evening event—these often include music, food, and after-hours access, which makes it one of the more unique things to do in Chicago at night.

14. Chicago’s Food Scene (Deep Dish Pizza, Hot Dogs, Italian Beef)

Chicago is one of those cities where you can’t separate the experience from the food. On my first night, I ordered a Chicago style deep dish pizza at Lou Malnati’s. The buttery crust, the thick layer of cheese, and the tangy tomato sauce—it was a meal and a memory rolled into one. Some call it heavy, but after walking all day along the Chicago Riverwalk, I thought it was perfect.

I also tried an Italian Beef sandwich at Portillo’s—juicy, messy, and absolutely worth it. Add in a Chicago-style hot dog (no ketchup, always piled high with toppings), and you’ve got a food scene that feels like a cultural introduction.

What I loved most, though, was branching out beyond the classics. Dinner at Siena Tavern in River North showed me the modern side of Chicago dining, while Fulton Market introduced me to innovative spots like Pizzeria Portofino right by the water. For couples looking for cool things to do in Chicago, sharing a progressive dinner across neighborhoods is an experience in itself.

Traveler’s tip: If you’re short on time, sign up for a food tour. It’s one of the most fun things to do in Chicago for adults—you get history, walking, and bites of all the city staples in a few hours.

15. Wrigley Field (or Catching a Game)

Even if you’re not a die-hard baseball fan, catching a game at Wrigley Field is a rite of passage. Built in 1914, it’s one of the most iconic stadiums in America, home to the Chicago Cubs. I went on a sunny afternoon, and the atmosphere was electric—fans singing, kids with foam fingers, locals chatting about stats like they were old friends.

What struck me was the sense of community. Wrigleyville, the neighborhood surrounding the stadium, transforms into a massive block party on game days. Sports bars spill onto the sidewalks, and even if you don’t have tickets, being in the area is one of the most fun things to do in Chicago for young adults.

Pro tip: If baseball isn’t your sport, Chicago’s energy around games still makes it worthwhile. From Chicago Bulls basketball at the United Center to Chicago Bears football at Soldier Field, sporting events are woven into the city’s cultural fabric. For couples, it’s surprisingly romantic—cheering side by side with thousands of fans becomes one of those shared experiences you’ll talk about long after.

Hidden Gems & Pleasant Surprises

As much as I loved the headliners, what stuck with me were the smaller discoveries—the little surprises that don’t always make the “top 10 things to do in Chicago” lists.

One evening, I stumbled into the Salt Shed, a new live music venue that instantly became one of my favorite Chicago cultural spots. The energy was raw, the crowd local, and it felt worlds away from Navy Pier’s touristy vibe.

In Logan Square, I joined friends at Guild Row, a creative community hub where artists, chefs, and musicians gather. It wasn’t in any guidebook, but it gave me a glimpse into Chicago neighborhoods beyond the Loop.

Even wandering through Printer’s Row during the annual Lit Fest was magical—streets lined with book stalls, readings, and hidden courtyards buzzing with conversation. For couples looking for things for couples to do in Chicago this weekend, these types of community-driven events feel authentic and romantic at the same time.

And sometimes, it was as simple as watching ART on THE MART light up the skyline after dark or sitting by Buckingham Fountain as the jets danced to music. Those quiet, unexpected moments reminded me that some of the best things to do in Chicago are free.

Practical Tips for First-Time Visitors to Chicago

Timing matters here. From my visits, I found spring and fall to be the sweet spots. In May, the city is in bloom—perfect for walking through the Chicago Botanic Garden or along Maggie Daley Park. Fall brings crisp air and events like the Chicago Marathon, when the city’s pride is on full display. Summers are lively with Chicago festivals and lakefront activities, while December offers holiday magic with Candlelight Concerts, the Headless Horseman Festival, and festive shopping districts lit up for the season.

Getting around: Public transportation is reliable, and the Chicago L connects most major attractions. Shoreline Sightseeing Water Taxis are a fun alternative, giving you skyline views while getting from Navy Pier to the Museum Campus. Rideshares are plentiful, but I relied mostly on the L trains and walking—it’s the best way to soak in Chicago architecture.

Budgeting: Don’t think the city has to be expensive. Free things to do in Chicago today include exploring Millennium Park, watching street performances on the Magnificent Mile, or enjoying a night of ART on THE MART by the river. To stretch your dollars, look into passes like Chicago CityPASS or Chicago C3® tickets—they cover museums and observation decks at a fraction of the cost.

Safety: Chicago felt welcoming, but like any big city, I kept an eye on my surroundings, especially at night. Stick to well-lit areas, and you’ll be fine. Locals were always quick to help with directions if I looked lost.

Final note: Pack comfortable shoes. Between exploring the Chicago Riverwalk, the Magnificent Mile, and neighborhoods like Wicker Park or Fulton Market, you’ll walk a lot. But honestly, that’s where you’ll find some of the coolest things to do in Chicago—the hidden murals, the family-run restaurants, and the unexpected views of Lake Michigan that make the city unforgettable.

Conclusion: Why Chicago is Worth a First (and Second) Visit

Looking back, I realize my first visit to Chicago was more than just a checklist of attractions—it was a layered experience of culture, food, architecture, and people.

The best things to do in Chicago weren’t always the obvious ones. Sure, standing on the Skydeck at Willis Tower or taking a river cruise gave me those iconic skyline moments, but sipping coffee in a Fulton Market café or catching a local festival in Lincoln Park felt just as memorable.

What makes Chicago stand out is its balance. It has the scale of New York City, the friendliness of a small Midwestern town, and a cultural depth that keeps surprising you.

Whether it’s free things to do in Chicago today like strolling Millennium Park, or seasonal musts like ice skating in December, the city offers something for every type of traveler.

And honestly, it’s the kind of place you want to return to. I left with a long list of unique things to do in Chicago still waiting—like more Chicago neighborhoods to explore, another game at Wrigley Field, and more restaurants that locals insisted I try. It’s one of those cities that stays with you, nudging you back again with the promise of new discoveries each time.

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