A city that blends bold architecture with deep-rooted culture, Chicago is where iconic skyscrapers meet the blues, jazz, and a legendary food scene. The tall, historic buildings that make up Chicago’s iconic skyline are the first thing to draw the eye, but it’s exploring the city that really sweeps visitors off their feet, from walking through the city streets to cruising down the river that cuts right through them. Chicago is a city that can be enjoyed from the water or the concrete in equal measure. Take an architecture tour on the water, stroll along the Riverwalk, and catch a show at Chicago’s historic theater. Every corner of the Windy City has a story to tell. And a bite to eat. Chicago’s food scene will have you constantly looking forward to your next bite, from deep dish pizza and Chicago-style hot dogs to jibarito and Michelin-rated restaurants. Whether you’re here for the music and views or the food and family fun, Chicago delivers an energy that’s both big-city and inviting.
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Must-See Attractions
Music Box Theatre
Step back in time at the Music Box Theatre, a 1929 movie palace still dazzling with vintage charm. Catch indie films, cult classics, or festivals in an atmosphere that feels like pure cinematic magic.
Chicago Loop
Downtown Chicago’s beating heart, The Loop is where soaring skyscrapers, iconic public art, and the city’s bustling energy collide. Home to landmarks like the Willis Tower and Millennium Park, The Loop is the city’s ultimate urban playground.
Chicago Riverwalk
Stretching along the Chicago River, the Riverwalk is a lively promenade filled with cafes, art, and stunning skyline views. Day or night, it’s one of the best ways to soak in the spirit of the city.
The 606
Once an old railway line, The 606 is now an elevated green trail perfect for walking, biking, and exploring public art. It’s where locals go to unwind and where you can take in city views from a fresh perspective.
The Green Mill
Step into jazz history at The Green Mill, a legendary club once frequented by Al Capone. With live music nearly every night, it’s a Chicago nightlife experience that’s soulful, stylish, and timeless.
Featured Tour
Chicago Architecture River Cruise
See Chicago from a whole new perspective as you cruise the river with an expert guide sharing the city’s architectural secrets. From historic landmarks to modern skyscrapers, every turn offers a stunning view of world-class design. The skyline shines brightest from the water, with photo-worthy angles you won’t find anywhere else. Relax, enjoy, and let the city’s story unfold right before your eyes.
Family-Friendly Fun
Lincoln Park Zoo
One of the country’s oldest zoos, the Lincoln Park Zoo is completely free and delights families with animals from around the globe. It’s a fun and educational escape right in the heart of the city.
Shedd Aquarium
From playful penguins to vibrant coral reefs, Shedd Aquarium brings the underwater world to life. Kids and adults alike will be amazed by the interactive exhibits and unforgettable marine encounters.
Millennium Park
A Chicago favorite, Millennium Park is where families gather to see Cloud Gate—better known as “The Bean.” With splash-worthy fountains, gardens, and free concerts, it’s the perfect spot for all ages to enjoy a greener side to the Windy City.
Places to Eat
Places to Stay
Best Time to Visit
As a Midwest city, Chicago may experience all four seasons, but there are two distinct times to visit: the warm, sun-soaked months surrounding summer and the cold, grey months that comprise winter. The city undoubtedly shines brightest from late spring through early fall, when outdoor festivals, lakefront strolls, and rooftop dining come alive. Summer brings buzzing energy with concerts, food events, and baseball season in full swing. For fewer crowds, late September to October is ideal, with crisp weather and colorful foliage. Despite what some might say, winter does have its own charms that make it worth a visit, from ice skating to holiday markets and the twinkling lights that pop up all over the city. Just be sure to dress warmly; layers and a long, down coat can do wonders for staving off the cold. And with plenty of indoor attractions—the Art Institute, Garfield Park Conservatory, the Harold Washington Library, and more—you never have to brave the cold for long. Chicago’s fun mix of endless activities and Midwest charm adds a touch of warmth to the Windy City in every season.
