Top Activities and Tours in Chicago

From guided tours to outdoor adventures — find the best activities and tours in Chicago with curated picks, local tips, and free itinerary planning tools.

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🎯 Activities and Tours in Chicago

  • Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO — Access top Chicago attractions, tours and activities with Go City's Explorer Pass. Save on entry to your choice of up to seven top things to do. Hop-on a Big Bus tour for an introduction to the city, check out the panoramic views from the 103rd floor at SkyDeck Chicago or 94th fl
  • Flyover in Chicago — The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll e
  • Chicago River 45-Minute Architecture Tour from Magnificent Mile — 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 archit
  • Chicago Architecture River Cruise — 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 his
  • Original Chicago Architecture Interiors Tour: Dazzling Interiors — UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's exclusively offered interiors-themed tours in Chicago for more than a decade, and that's INSIDE CHICAGO WALKING TOURS. Our "Worl
  • Chicago's Chinatown Food and Walking Tour — Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked Top 10 in America by USA Today & Top 20 in the world by Tripadvisor, for a day of interesting stories and s
  • Chicago in a Day Walking Tour: Food, History & Architecture — Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging in delectable local cuisine. From deep-dish pizza to hidden gems, savor the flavors of Chicago
  • Chicago Architecture Center River Cruise aboard First Lady — The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview o
  • 360 CHICAGO Observation Deck Admission — The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers. Located in the heart of downtown on Mich
  • Downtown Chicago Walking Pizza Tour — This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold Coast & River North. Compare two American pizzas vs. two Italian pizzas to understand how pizza evolved as an immigrant food. Explor
  • Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings — Recently voted one of TripAdvisor's top food tours in the US. Discover the sweet side of the Windy City on the Underground Donut Tour, Chicago’s Delicious Donut Adventure. We’ll kick things off at the legendary Doughnut Vault, tucked beside the historic Merchandise Mart, where
  • Skydeck - Willis Tower Admission — Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping views and is full of interactive exhibits. To complete your
  • Chicago CityPASS® — Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your tickets, you’ll have plenty of time to explore the best sights. Chi
  • Chicago River 90-Minute Architecture Tour — 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 thr
  • Historical and Architectural Chicago Fireboat River & Lake Cruise — Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in between! Our flagship vessel is a retired Chicago fire boat, the
  • Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline — Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riverfront landmarks to groundbreaking modern skyscrapers. Explore the Loop’s civic, financial, and architectural core, adm
  • Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich — On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through so
  • Chicago Walking Tour: Historic Treasures of Chicago — Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the most memorable buildings, many of which are featured on this tour. After the World's Columbian Exposition of 1893, Chic
  • Chicago City Tour with Architecture River Cruise Option — Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned architecture including the world's first skyscrapers
  • 2-Hour Chicago Lakefront & Museum Campus Segway Tour — Looking for fun things to do in Chicago? Look no further! Join one of our professional guides on a scenic 6-8 mile Chicago Segway tour. Glide effortlessly through the fragrant garden paths of Grant Park to marvel at the iconic Buckingham Fountain. Enjoy the breeze as you explore
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