🏙️ Chicago is a city where centuries of history meet modern life on every street corner. Whether you're visiting for the first time or returning to discover more, there are endless Things to do in Chicago from world famous attractions and guided tours to unique local excursions and immersive cultural activities that will leave you with unforgettable memories.
Below, you'll find a helpful breakdown of top Chicago attractions, practical travel tips, and curated experiences to help you plan your visit. Book your tickets early, as the most popular tours fill up fast.
Chicago's architectural marvels, world-class museums, and lakefront beauty create an unforgettable urban experience. From towering skyscrapers to cultural institutions, the Windy City offers iconic attractions that showcase its rich history and vibrant spirit.
Discover Chicago's rich architectural heritage and historic sites
World-renowned museums and cultural institutions
Contemporary attractions and iconic modern landmarks
Chicago's culture blends Midwest friendliness with big-city sophistication. Experience deep-dish pizza traditions, world-class jazz and blues heritage, and vibrant neighborhoods each with their own distinct character and community spirit.
From luxury shopping on the Magnificent Mile to unique boutiques in trendy neighborhoods, Chicago offers diverse retail experiences. Discover everything from high-end fashion to local artisan goods and vintage finds throughout the city.
Chicago's extensive park system includes lakefront beaches, urban gardens, and recreational spaces. The city's commitment to green space provides residents and visitors with beautiful areas to relax, exercise, and enjoy outdoor activities year-round.
Beyond famous attractions, Chicago holds countless secrets waiting to be discovered. From hidden speakeasies to unique museums, these lesser-known spots offer authentic experiences that reveal the city's true character and local flavor.
Navigate Chicago like a local with insider knowledge about transportation, neighborhoods, and customs. These practical tips will help you make the most of your visit while avoiding common tourist pitfalls and embracing the city's authentic character.
Navigate Chicago's efficient public transportation system
Choose accommodations that match your Chicago experience goals
Embrace Chicago customs and local social norms
Discover Chicago through expertly guided experiences that reveal the city's architecture, history, and culture. From boat tours along the Chicago River to food walks through diverse neighborhoods, these excursions offer insider perspectives and memorable moments.
Book architecture boat tours well in advance during summer months as they sell out quickly, especially on weekends.
Navigate Chicago's attractions, dining, and transportation with our interactive map. Discover the best routes between destinations and find hidden gems throughout the city's diverse neighborhoods and iconic landmarks.
Use the map to plan efficient routes and discover nearby attractions, restaurants, and services during your Chicago visit.
Read what fellow travelers say about their Chicago experiences. These authentic reviews provide insights into must-see attractions, local favorites, and practical tips from visitors who have explored the Windy City's many offerings.
⭐⭐⭐⭐⭐ "Architecture and Deep-Dish Paradise"
Chicago exceeded all expectations! The architecture boat tour was absolutely stunning, and we couldn't get enough of the deep-dish pizza. Millennium Park and the Art Institute were incredible. Three days wasn't nearly enough time to see everything. – Sarah M., Canada
⭐⭐⭐⭐⭐ "Perfect Weekend Getaway"
Loved the mix of culture, food, and friendly people. Navy Pier was fun for the family, and the jazz clubs in the evening were fantastic. The CTA made getting around so easy. Already planning our return trip! – Michael R., United States
⭐⭐⭐⭐ "Great City for Food Lovers"
The food scene in Chicago is phenomenal beyond just pizza. We did a food tour through different neighborhoods and discovered amazing local spots. The lakefront is beautiful, and people are genuinely welcoming. – Emma K., United Kingdom
Q: What's the best way to book Chicago attraction tickets in advance?
A: Purchase tickets online through official websites for major attractions like Willis Tower Skydeck and museums. Many offer discounted advance pricing and skip-the-line access during peak season.
Q: When is the best time to visit Chicago?
A: Late spring through early fall offers the best weather and outdoor activities. Summer is peak season with festivals and events, while winter can be very cold but offers holiday attractions and fewer crowds.
Q: How do I get around Chicago without a car?
A: Chicago has excellent public transportation with the CTA train and bus system. The city is very walkable downtown, and rideshare services are readily available. Many attractions are accessible via the efficient L train system.
Q: How many days should I spend in Chicago?
A: Plan at least 3-4 days to see major attractions, experience the food scene, and explore different neighborhoods. A week allows for deeper exploration of museums, day trips, and more leisurely neighborhood discovery.
Q: Do I need to book restaurant reservations in advance?
A: Popular deep-dish pizza places and upscale restaurants often require reservations, especially on weekends. Many neighborhood spots accept walk-ins, but calling ahead is recommended for dinner during busy periods.
Q: What should I know about Chicago's tipping culture?
A: Standard tipping is 18-20% at restaurants and bars. Taxi drivers expect 15-20%, and hotel staff appreciate small tips for services. Architecture boat tour guides typically receive tips based on service quality.
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Start discovering Chicago with WandeGo — the city is waiting.
Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building. Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including: John Hancock Center: An iconic skyscraper that defines the Chicago skyline. Wrigley Building: Known for its distinctive white facade and clock tower. As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities. Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.
From USD 39 — ★ 4.8365893 (16994 reviews)
Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today. The Chicago River Architecture Tour is the most authentic and encompassing Chicago experience the city has to offer.
From USD 45 — ★ 4.708223 (10933 reviews)
Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.
From USD 28 — ★ 4.6527314 (3588 reviews)
Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views of Chicago's renowned skyscrapers from a unique vantage point. This tour offers an amazing opportunity to admire the city's breathtaking skyline and architectural wonders. Sunday – Friday Cruises departing prior to 8:00pm feature recorded narration of the city’s skyline, cruises departing after 8:00pm enjoy some music and the sounds of Lake Michigan aboard our Groove Cruise. November - April 9 tours are 30 minutes. Highlights: Spectacular views of Chicago's famous skyscrapers Onboard bar serving refreshing drinks Relaxing and enjoyable sightseeing cruise Experience Chicago like never before on this serene and scenic Lake Michigan boat tour. Remember to bring your camera to capture those social media worthy photos!
From USD 34 — ★ 4.44 (950 reviews)
Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline. Lively, knowledgeable tour guides bring Chicago’s rich history to life with fun stories and interesting facts. Relax and unwind on a scenic tour of the city from the unique perspective of the Chicago River and Lake Michigan. Welcome aboard!
From USD 46 — ★ 4.695712 (723 reviews)