Chicago tours

Things to do in Chicago

Skyscrapers rise like modern cathedrals, jazz melodies float from hidden clubs, and the scent of deep-dish pizza drifts along bustling streets. Chicago is a city where innovation meets tradition — bold, diverse, and endlessly captivating. Choosing your Chicago tour that is private and customizable lets you step into the Windy City's story in a way that feels deeply personal — from its glittering skyline to its neighborhood soul. Top 10 Must-See Attractions on Your Chicago Tour Millennium Park Pause before the gleaming curves of Cloud Gate ("The Bean") and stroll through vibrant gardens where your guide can share insider stories of Chicago’s transformation. Willis Tower Skydeck Ride high-speed elevators during your journey to the Skydeck, then step out onto the thrilling glass-floored ledge for views stretching across four states. Navy Pier Breathe in the lake air as you explore gardens, amusements, and waterfront dining — all woven into your day at your own pace. Art Institute of Chicago Immerse yourself among masterpieces from Monet, Van Gogh, Hopper, and Warhol, guided through one of the world’s greatest art collections. Chicago Riverwalk Follow your guide along this lively urban waterfront where every bridge and building reveals another layer of the city’s character. Magnificent Mile Stroll along Michigan Avenue where historic landmarks and luxury boutiques line the grand boulevard of your Chicago experience. Wrigley Field Feel the magic of a century-old ballpark with your guide bringing to life the legends and lore of the beloved Chicago Cubs. Field Museum of Natural History Stand in awe of "Sue" the T. rex and explore ancient cultures and sparkling gems, tailored around your interests. Museum of Science and Industry Interact with hands-on exhibits and historic marvels like a WWII submarine, making this part of your Chicago journey one of discovery and wonder. Chicago Cultural Center Step under the largest Tiffany dome in the world and enjoy free exhibits or performances, easily woven into your customized tour. Explore Chicago Off the Beaten Path with Your Guide Pilsen’s Street Art and Murals Capture the colorful murals and deep cultural pride of Pilsen, guided through the heart of Latino creativity. Andersonville’s Global Flavors Taste your way through one of Chicago’s most vibrant neighborhoods where every bite reflects global traditions. Garfield Park Conservatory Escape into lush glasshouses where your guide can highlight rare plants and hidden corners known mostly to locals. Chicago Pedway System Discover the hidden side of downtown Chicago on foot, using the Pedway’s maze of tunnels and bridges as your personal shortcut. The 606 Trail Cycle or stroll along a former rail line turned greenway, connecting neighborhoods and public art projects on your private journey. Day Trip Ideas to Add to Your Chicago Itinerary Evanston’s Historic Lakeshore Enhance your day with a lakeside stroll through university gardens, charming neighborhoods, and art galleries. Oak Park’s Frank Lloyd Wright Legacy Follow your guide into the world of America's greatest architect — where innovation lives in every brick and timber. Milwaukee’s Beer and Culture Scene Venture just north to discover vibrant arts districts, lakeside beauty, and craft breweries — all tailored to your interests. Indiana Dunes National Park Add a breath of fresh air to your Chicago itinerary by exploring sweeping dunes and crystal-clear lake shores just an hour away. Travel Tips for Your Chicago Tour Best Times for Your Journey: Late spring and early fall offer sunny days perfect for outdoor explorations and lakefront adventures. Getting Around During Your Tour: Your guide will help you navigate public transit, river taxis, and charming neighborhood strolls for a seamless experience. What to Wear for Your Chicago Tour: Layer up — Chicago's breezes can surprise you even in summer. Comfortable shoes are a must for city walks and museum visits. Local Etiquette: Chicagoans appreciate politeness and quick movement in busy areas. A warm smile and a thank-you go a long way on your journey. Explore Chicago Your Way In Chicago, bold skyscrapers frame secret gardens, and every corner tells a new story. Whether you dream of exploring famous museums, uncovering vibrant street art, sampling iconic foods, or strolling the lakeshore, your Chicago tour becomes as vivid and unique as the city itself. With ToursByLocals, your Chicago journey becomes private, flexible, and shaped entirely around what you want to see and feel. Find your perfect guide and let Chicago’s energy, creativity, and warmth open itself to you — one unforgettable step at a time.