Chicago, the Windy City, is a melting pot of culture, entertainment, and natural beauty, offering something for every kind of traveler. From the culinary delights of Michelin-starred restaurants to the electric atmosphere of major sporting events, concerts, and festivals, Chicago is a city that never sleeps. Here are the top five things to do in Chicago, covering the best of its dining scene, sports, music, museums, and beaches.

#5 – Tourist Attractions
Chicago is filled with fantastic tourist attractions that cater to all interests. Millennium Park is home to the iconic Cloud Gate sculpture—known as “The Bean” – where citizens and tourists gather with friends and family to take pictures. Navy Pier is another standout attraction, offering rides, restaurants, shops, and beautiful views of Lake Michigan, along with the city’s iconic Ferris wheel.
Fun fact: WEGO’s prom will be held there!
#4 – Explore the City’s Rich Cultural Heritage at Its Museums
Chicago boasts some of the world’s most impressive museums. The Art Institute of Chicago is a must-visit for art lovers, showcasing masterpieces by Picasso and Van Gogh. The Field Museum offers a journey through ancient civilizations and natural history, while the Adler Planetarium takes visitors on a cosmic adventure through the stars and beyond.

#3 – Zoos and Aquariums
Chicago is home to several zoos and aquariums, including Lincoln Park Zoo, Brookfield Zoo, and the Shedd Aquarium. Each location features a wide variety of animals and interactive exhibits, from marine life to land mammals, all set in beautiful park surroundings. These destinations are ideal for families, animal lovers, or anyone looking for an educational yet entertaining experience.

#2 – Sporting Events
It is impossible to talk about Chicago without mentioning sports and the value they hold for true Chicagoans. From the legendary ‘85 Bears to the curse-breaking 2016 Cubs, the Windy City has its fair share of historic sports champions. The dominance of the 1990s Bulls, led by Michael Jordan, brought six championships in just eight seasons.
Sporting events hold deep significance for many residents, uniting the diverse population of the 312. These live events provide a cultural touchstone for the city, bringing people together even during rough seasons. Through every win and loss, fans remain loyal and proud.
#1 – Restaurants
Whether you are a lifelong resident or visiting for the first time, there is always something new and delicious to discover. Sampling the food scene is easily one of the best things to do in Chicago.
Prime & Provisions is a renowned steakhouse that combines modern flair with classic steakhouse traditions. The upscale atmosphere makes it perfect for special occasions. Reservations are recommended, especially during peak hours, with steaks ranging from $40 to $100. Beatnik on the River offers stunning views along the Chicago River and is known for its eclectic decor and globally inspired menu, featuring a mix of Mediterranean and fusion dishes. Again, reservations are highly recommended.
For a more affordable – but equally satisfying – option, Flub A Dub Chub’s specializes in classic Chicago comfort food. With hot dogs, Italian beef, and burgers that won’t break the bank, it’s perfect for a casual night out.
Chicago’s culinary scene reflects the city’s cultural richness – making dining out a memorable part of any visit.