Top 10 Things to See and Do in Chicago | The Ultimate 2025 Travel Guide

Chicago, the third-largest city in the United States, is a vibrant hub of culture, history, and gastronomy. Nestled along the shores of Lake Michigan, this city offers a wide array of activities to delight any visitor.

With its iconic skyline, unique neighbourhoods, and rich cultural scene, Chicago is a destination you simply can’t miss. If you’re unsure about the best time to visit, spring and summer are highly recommended for their pleasant weather. During these seasons, the city comes alive with festivals and outdoor events. On the other hand, if you’d prefer to avoid the heat, travelling in September or October is ideal.

From breathtaking observation decks to captivating museums and an exceptional culinary scene, here’s a guide to some of the best things to do in the Windy City.

The Art Institute of Chicago

To start your day, The Art Institute of Chicago is an excellent choice. This prestigious museum houses one of the most impressive art collections in the world, featuring everything from Renaissance masterpieces to contemporary art. Located in Grant Park, the museum offers a deeply educational and aesthetic experience best enjoyed in the morning, before it gets crowded, or throughout the day, as there is so much to explore.

In addition to its extensive permanent collection, The Art Institute is renowned for its temporary exhibitions, which showcase masterpieces from museums and private collections around the world. Among its most famous pieces are American Gothic by Grant Wood and Nighthawks by Edward Hopper. Every visit offers something new, as the exhibits rotate regularly.

The museum also provides a variety of educational programs and activities for all ages, from workshops for children to lectures and guided tours. Its gift shop and on-site cafés are perfect for picking up a souvenir or taking a break while exploring the galleries.

MCA Chicago

Continuing with museums, for those interested in contemporary art, a visit to the Museum of Contemporary Art Chicago (MCA) is a must. With its innovative exhibitions and artistic events, the MCA offers a fascinating window into the world of modern art.

The MCA houses a permanent collection that includes works by some of the most influential contemporary artists in the world, such as Jeff Koons, Cindy Sherman, and Kara Walker. Additionally, the museum is renowned for its temporary exhibitions, which offer fresh perspectives and challenges in contemporary art. These exhibits often explore current social and cultural themes, providing visitors with a thought-provoking and reflective experience.

The MCA building, designed by architect Josef Paul Kleihues, is a work of art in itself, featuring a minimalist and elegant design that perfectly complements the pieces it holds. Conveniently located in downtown Chicago near Lake Michigan and the Magnificent Mile, the museum is an ideal stop on any tourist itinerary.

Beatnik on the River

After a morning filled with art, it’s time to recharge, and Beatnik on the River is an excellent choice. With its bohemian ambience along the river, the restaurant delights diners with an eclectic menu that blends international flavours in a relaxed and exotic setting.

The interior of Beatnik is decorated in a boho-chic style, with design elements that transport diners to a tropical and exotic atmosphere. Dim lighting and soft music create a cosy ambience, perfect for a romantic meal or a gathering with friends.

Beatnik’s menu is equally impressive, offering a selection of dishes inspired by cuisines from around the world. From tapas and small plates to heartier options, every dish is crafted with fresh ingredients and artistic presentation. Be sure to try their innovative cocktails, which are the perfect complement to a special afternoon.

360 CHICAGO

For a breathtaking panoramic view, visit 360 Chicago at the John Hancock Tower. From the 94th floor, you can marvel at the expanse of the city and Lake Michigan. The TILT attraction, a glass platform that tilts outward from the building, offers an unforgettable thrill for the adventurous.

The observatory also features an interactive exhibit where you can learn more about Chicago’s history and architectural landmarks. On a clear day, you can even see up to four states from the observation deck: Illinois, Indiana, Wisconsin, and Michigan, offering a truly awe-inspiring perspective.

For those seeking a more laid-back experience, the bar and café at 360 CHICAGO is a fantastic spot to enjoy a drink while soaking in the dreamy views. It’s the perfect place to relax after a morning exploring the city and gear up for the next adventures of the day.

Chicago Gangsters and Food Tour

In the mid-afternoon, embark on the Chicago Gangster and Food Tour. This guided experience combines the rich history of Chicago’s infamous gangsters with a tasting of its outstanding cuisine. You’ll explore historical sites while savouring some of the best bites the city has to offer.

The tour takes you through historic neighbourhoods like River North and the Loop, where you’ll learn about infamous figures like Al Capone and stories from the Prohibition era. The expertise and professionalism of the guides bring the stories to life with fascinating anecdotes and intriguing details.

In addition to the history, the tour includes stops at some of Chicago’s most iconic restaurants, where you can sample classic dishes like deep-dish pizza, Chicago-style hot dogs, and other local favourites. It’s an experience that delights both history buffs and food lovers alike.

The Comedy Clubhouse

For comedy lovers, The Comedy Clubhouse is a fantastic choice. Managed by the first developing comedian union, One Group Mind, this club provides a platform for emerging talent and guarantees an evening filled with laughter and good humour.

The Comedy Clubhouse stands out for its inclusive and community-oriented atmosphere. Here, emerging comedians have the opportunity to hone their craft in a supportive environment, while audiences enjoy fresh and original performances.

The club also hosts open mic nights and comedy competitions, adding an exciting and unpredictable element to each show. It’s the perfect place to discover new talent and enjoy a fun, laid-back evening. Additionally, the club fosters a sense of community among both the comedians and the attendees, creating a warm and welcoming atmosphere that makes everyone feel right at home.

Tanta

For an afternoon snack, Tanta will delight you with its authentic Peruvian cuisine. From fresh ceviches to the traditional lomo saltado, Tanta offers a unique culinary experience in a modern and inviting setting.

Chef Gastón Acurio, internationally renowned, has crafted a menu that celebrates the diversity and richness of Peruvian cuisine. Each dish is prepared with fresh ingredients and traditional techniques, offering an authentic culinary experience that delights the senses.

The atmosphere at Tanta is warm and contemporary, with decor that reflects the vibrant spirit of Peru. It’s the perfect spot to discover new flavors and enjoy tapas or a cocktail in the heart of Chicago.

iOTheater

For a night full of laughter, iO Theater is the birthplace of improvisation in the city. Offering high-quality comedy shows and interactive workshops, this theatre is renowned for its welcoming atmosphere and hilarious performances. iO Theater is known as the launching pad for many famous comedians, including Tina Fey, Amy Poehler, Mike Myers, and Jason Sudeikis. Its improvisation shows are dynamic and always different, providing a unique experience with every visit.

In addition to the performances, iOTheater offers workshops and improv classes for those who want to try their hand at comedy. It’s a great way to learn new skills and have fun in the process.

The Ledge

Another great option for exploring the city is The Ledge. You’ll need to head up to the Skydeck at the Willis Tower to step onto a glass balcony on the 103rd floor. You’ll feel the city beneath your feet, as looking down offers a completely new perspective of the city. Additionally, you can enhance this unique experience with the “Pie in The Sky” opportunity, enjoying the famous Giordano’s pizza while taking in the stunning views.

The Skydeck offers not only a visual experience but also an educational one, with exhibits that detail the history of Chicago and its architecture. It’s fascinating to learn about how the city has evolved over the years while observing its landscape from such great heights.

Additionally, The Ledge is the perfect spot for taking stunning photographs to capture your unique experience. It’s an exciting and unforgettable challenge that will make you see the city like never before.

smartbar

If you’re looking for nightlife, smartbar is the place to be. Known for its vibrant electronic music scene and DJ nights featuring some of the world’s top talents, this club offers excellent acoustics and an energetic atmosphere. It’s the perfect spot to dance and enjoy Chicago’s nightlife.

smartbar has been a cornerstone of Chicago’s music scene for decades, providing a platform for both local and international DJs. Its high-quality sound system ensures that every night offers an exceptional auditory experience. The club also hosts themed events and special nights, providing a diverse and exciting experience for attendees. Whether you’re a fan of electronic music or simply looking for a fun night out, smartbar is sure to impress.

Chicago is a city full of life and diversity. From its rich history and architecture to its vibrant cultural and gastronomic scene, there is always something new and exciting to discover. Whether you’re interested in breathtaking views, world-class art, delicious food, or thrilling nightlife, this city has everything you need for a memorable visit.

Explore curated travel tips, exciting activities, and must-see destinations that will help make your journey truly unforgettable at our Hype Destinations section.