Traveling to a new destination can sometimes feel overwhelming, especially with so many activities vying for your attention. It’s easy to get carried away while planning, just like I did before my trip to Chicago.
Before setting off for this iconic Midwest destination, I enthusiastically compiled an ambitious list of things to do. Let’s just say my itinerary was closer to a two-month adventure than a quick getaway. Thankfully, a friend of mine who calls Chicago home stepped in to guide me toward the city’s absolute highlights.
To simplify your planning, I’ve teamed up with my friend to put together a curated list of the coolest activities and experiences Chicago has to offer, perfect for first-time visitors (or anyone looking to rediscover the city).
Chicago boasts excellent train connections to major cities across the U.S. If you want to opt for a more sustainable mode of transportation, consider booking train tickets instead of flying. It’s a relaxing and eco-friendly way to kick off your trip!
Top Things To Do in Chicago
1. Discover Chicago from Above with a Bird’s Eye View
One of the most exciting ways to get to know a city is by starting with a bird’s-eye view. In Chicago, the 94th floor of the John Hancock building offers this experience in spectacular fashion.
The 360 Chicago Observation Deck provides unparalleled views of the cityscape, stretching as far as Lake Michigan. For those looking to elevate the experience (literally), try the TILT—a glass and steel platform that leans outward, giving you a vertigo-inducing perspective of the Magnificent Mile far below.
Tickets to the observation deck cost a little over $30 for adults, and TILT requires an additional fee. While the add-on may not fit every budget, it’s definitely an option for thrill-seekers. To save time, purchase tickets online ahead of your visit.
Pro Tip: The observation deck also features a bar where you can sip a drink while soaking in the panoramic views—a more relaxed way to enjoy the skyline.
2. Shop On Magnificent Mile
The Magnificent Mile, a renowned stretch of Michigan Avenue, is the ultimate destination for shopping enthusiasts and sightseers alike. This bustling area features everything from high-end boutiques to trendy fashion outlets, along with upscale restaurants and elegant hotels.
As you wander, you’ll come across iconic landmarks like the historic Chicago Water Tower, the impressive Wrigley Building, and the towering John Hancock Center. Each structure adds a unique charm to the avenue, making it a treat for both shoppers and architecture admirers.
For a bit of adventure, try out an escape room experience at The Escape Game, located nearby. It’s a fun break from shopping and perfect for groups looking for a challenge.
Did You Know? The Magnificent Mile ranks as one of the most expensive neighborhoods in the United States, with luxury rivaling Fifth Avenue in New York and Rodeo Drive in Beverly Hills. Living here comes with a hefty price tag!
While exploring, keep an eye out for the vibrant painted dog sculptures scattered throughout the area. These art pieces, depicting German Shepherds, were created as a tribute to police officers who have been injured or killed in the line of duty—a meaningful touch to the lively streetscape.
3. Chill at The LondonHouse Rooftop Bar
Imagine relaxing with a cocktail in hand while gazing out at the boats gliding along the Chicago River. If that sounds like your ideal evening, the rooftop bar at LondonHouse Chicago is a must-visit spot.
Housed in a historic 1920s building, LondonHouse is one of the city’s most centrally located hotels. Its tri-level rooftop offers sweeping views of the river, the Magnificent Mile, and even the shimmering expanse of Lake Michigan.
Whether you’re indulging in a signature cocktail or a refreshing mocktail, this rooftop experience is more than just drinks—it’s a chance to take in Chicago’s striking cityscape from one of its most iconic vantage points. A perfect way to wind down after a day of exploring.
4. Unwind in Millennium Park
First-time visitors to Chicago shouldn’t miss Millennium Park, a celebrated public space that combines striking art, lush greenery, and engaging activities. A highlight of any trip, this park offers something for everyone.
The iconic Cloud Gate, popularly known as “The Bean,” is one of the park’s most photographed features. Its reflective surface draws crowds daily, offering a playful perspective of the surrounding cityscape.
For those looking to escape the pace of city life, Lurie Garden provides a serene spot with its thoughtfully crafted landscape. Art enthusiasts can enjoy the rotating exhibits at the Boeing Galleries, which showcase fascinating outdoor installations year-round.
Chicago has so much more to offer beyond the well-trodden paths, with hidden gems that only locals know about.
Music lovers should check the schedule at the Jay Pritzker Pavilion, where free music festivals and performances take place. Even without a live event, the pavilion’s open lawn is an ideal spot for picnics, relaxation, or simply enjoying the setting sun.
During the holiday season, Millennium Park transforms into a festive wonderland. Activities like ice skating and rides on charming carousels make it a magical destination for winter visits. Whatever the season, this urban retreat offers a refreshing change of pace and endless opportunities to explore.
5. Wander the Chicago Riverwalk
The Chicago Riverwalk is much more than just a pedestrian path—it’s a dynamic waterfront destination that offers both relaxation and excitement. Stretching along the Chicago River, it’s a space where the city’s architectural beauty meets lively activities and serene moments.
What might first seem like a simple walkway reveals hidden treasures as you explore. Enjoy drinks at various outdoor bars, savor meals at riverside restaurants, or stop by the Chicago River Museum to learn about the history of this vital waterway. Along the way, you’ll also find intriguing outdoor art exhibits, adding a creative flair to the trail.
For those seeking a bit more action, consider taking a kayak tour or hopping on a boat cruise to view the city’s iconic skyline from a fresh perspective. Whether you visit during the day or at night, the Riverwalk offers a distinct and engaging atmosphere that’s hard to match anywhere else in Chicago.
During my stay in the city, the Riverwalk quickly became one of my favorite spots. Its mix of energy and calm made it a place I kept returning to, and I highly recommend adding it to your itinerary for an unforgettable Chicago experience.
6. Discover the Trendy West Loop
Chicago’s West Loop neighborhood offers a vibrant mix of history and modern charm. Once an industrial district filled with warehouses, it has transformed into a hotspot for food lovers, nightlife enthusiasts, and visitors seeking a unique side of the city.
The area’s standout attraction is Fulton Market, a trendy enclave where many of Chicago’s best restaurants and bars have set up shop. The industrial aesthetic remains, but it’s paired with chic design and a lively atmosphere that draws locals and tourists alike.
If you’re a coffee fan, make sure to visit Sawada Coffee, a quirky café tucked inside a building adorned with bold graffiti. Their signature drink, the “Military Latte,” combines matcha, espresso, and cocoa for a one-of-a-kind caffeine fix. Even non-coffee drinkers will find something to enjoy on their inventive menu.
The West Loop isn’t just about food and drinks; it’s a place where creativity meets culture, making it one of the most compelling neighborhoods to explore—or even stay in—during your Chicago adventure.
7. Have a Night Out at Noyane Rooftop Bar
While the LondonHouse rooftop might be the go-to spot for skyline views, Noyane offers an experience that rivals its allure. Perched atop the Conrad Chicago, this rooftop gem provides an inviting atmosphere that feels both modern and intimate—a perfect setting to wind down after a day in the city.
The space features sleek furnishings, a cozy fire pit, and a well-stocked bar ready to craft nearly any drink to suit your mood. Whether you’re sipping a classic cocktail or trying something adventurous, the ambiance at Noyane elevates every moment.
Hungry? Don’t miss the opportunity to try their Japanese-Peruvian fusion menu. The dishes are thoughtfully prepared, blending bold flavors with impeccable presentation to make your evening unforgettable.
Though its views might not rival the heights of some other rooftop destinations, Noyane’s exceptional vibe and culinary offerings make it a standout spot for an elegant evening in Chicago.
8. Ride the Ferris Wheel at Navy Pier
Venture out from downtown Chicago and make your way to Navy Pier, a sprawling 1-kilometer-long waterfront destination along Lake Michigan. This lively area is packed with attractions, making it easy to spend an entire day exploring its offerings.
From a sensory maze and botanical garden to a classic musical carousel and the Chicago Children’s Museum, Navy Pier has something for visitors of all ages. But the centerpiece is undoubtedly the Centennial Wheel, a 60-meter Ferris wheel that provides breathtaking views of both the Chicago skyline and the expansive lake. Its smooth, gentle rotations make it a delightful ride for families and solo travelers alike.
Tickets for a single ride cost $20 for adults and $12 for children, making it a splurge-worthy activity for those looking to capture unique perspectives of the city. To skip the wait, purchasing tickets online in advance is highly recommended.
Pro Tip: If you’re planning to explore multiple attractions, consider investing in a Chicago Go City Pass. It can save you up to 50% on admission to top sites, including Navy Pier experiences.
9. Wander Around the Old Town & Pop Into Its Cutest Little Cafe
Chicago isn’t just a city of towering skyscrapers. Beyond downtown, neighborhoods like Old Town offer a completely different charm. With its Victorian-era architecture, cobblestone streets, and a distinctly quaint atmosphere, Old Town feels like a slice of Britain transplanted into the Midwest.
The area is a haven for boutique shops, cozy pubs, and artisanal cafés, making it perfect for a leisurely afternoon. Among its highlights is the 3 Arts Club Café, tucked inside Restoration Hardware, a luxury home furnishings store. This café isn’t just a place to grab a coffee—it’s a visual masterpiece.
Step inside, and you’ll be greeted by crystal chandeliers hanging beneath a grand glass ceiling, a tranquil fountain in the center, and lush greenery adorning every corner. It feels less like a café and more like an event venue, making every visit an experience.
Despite its luxurious setting, the prices are surprisingly reasonable, and the menu offers excellent options for breakfast or a coffee break. Whether you’re sipping a cappuccino or indulging in a chai latte, sitting beneath those chandeliers is a moment of pure delight and one of the most memorable experiences Old Town has to offer.
10. Skydeck Chicago at the Willis Tower
This experience is not for the faint of heart or those uneasy with heights, but it’s a must-try for thrill-seekers visiting Chicago. The Willis Tower, once the tallest building in the world, stands at over 440 meters tall and remains one of the city’s most iconic landmarks.
Built in 1973, the tower held the title of the world’s tallest skyscraper for nearly 25 years. Its Skydeck, located on the 103rd floor, offers panoramic views of the city and beyond. Reaching this height takes just 60 seconds by elevator—a ride so rapid you can feel the change in pressure.
Once at the top, you’ll understand why this attraction is so popular. Beyond the jaw-dropping views, the highlight is stepping onto one of the glass balconies, which extend more than a meter from the building’s facade. Looking straight down through the glass beneath your feet is both exhilarating and unnerving, making it a unique way to experience the city.
Don’t forget to snap a photo—the Skydeck is one of the most photogenic spots in Chicago and perfect for Instagram-worthy shots. While the Skydeck offers incredible views, you might want to explore some of Chicago’s best free experiences, loved by locals, for a more authentic taste of the city.
Tickets start at $36, and purchasing them online in advance is highly recommended to avoid long waits.
While the Skydeck offers incredible views, you might want to explore some of Chicago’s best free experiences, loved by locals, for a more authentic taste of the city.
Pro Tip: Save on multiple attractions by getting a Chicago Go City Pass, which can cut up to 50% off admission prices for major destinations like the Skydeck.
11. Chinatown Eats – One Bite at a Time
Chicago’s Chinatown is a vibrant and flavorful destination that deserves a spot on your itinerary. This bustling neighborhood offers a rich cultural experience, where food lovers can indulge in a variety of authentic dishes and explore its unique charm.
Start your journey by sampling regional specialties at local restaurants, grabbing bites at small dim sum spots, or enjoying a calming cup of tea at one of the area’s traditional teahouses. The culinary options are abundant, and the flavors are as diverse as they are delicious.
Once you’ve had your fill, delve deeper into the cultural essence of Chinatown by visiting the American Museum of Chinese History. This museum provides an insightful look at the journey and contributions of Chinese immigrants, enriching your understanding of this dynamic community.
Chinatown is more than a place to eat—it’s a lively area where tradition and modernity blend seamlessly. Whether you’re savoring a comforting bowl of noodles or exploring its cultural landmarks, this neighborhood offers an unforgettable slice of Chicago.
12. Take in the Skyline from North Avenue Beach
To wrap up your Chicago adventure, head to North Avenue Beach, a beloved spot that combines relaxation with incredible views. Located in Lincoln Park, this beach is a go-to destination for locals and visitors alike, offering a picturesque escape from the urban hustle.
During the summer, the area is buzzing with swimmers, sunbathers, and beach volleyball enthusiasts. Yet, even in the cooler months, the lakeshore path remains lively with bikers, rollerbladers, and those out for a peaceful walk along the water.
The real magic, however, lies in the unmatched view of the city’s skyline. Whether you visit during the day to see the buildings gleaming against the blue sky or arrive at dusk to witness the sun setting behind the towering structures, North Avenue Beach offers a perspective that is nothing short of mesmerizing.
One of my most cherished moments in Chicago took place here. On my final evening in the city, I sat by the lake as the lights of the skyline reflected on the water. The scene was so moving that when a passing jogger stopped and remarked, “Isn’t it beautiful?” I could only nod, completely overwhelmed by the city’s charm.
This serene and awe-inspiring spot is more than just a beach—it’s a place where Chicago’s spirit comes alive. If you’re seeking a memorable way to end your time in the city, North Avenue Beach is the perfect choice.
