Discover the top experiences in Chicago, United States. From sustainable eco-tourism to hygge-inspired experiences, these carefully selected options embody everything we love about mindful, authentic travel.
1. Chicago Highlights Running Tour
Get your workout in while exploring Chicago’s most iconic sights on this guided running tour through the city. Led by a knowledgeable local runner, you’ll jog at a comfortable pace past landmarks such as Millennium Park, the Bean, Buckingham Fountain, and the Museum Campus. Along the way, your guide shares fun facts and historical insights about Chicago’s architecture, culture, and lakefront beauty. With frequent stops for photos and breathtaking skyline views, this experience blends fitness and exploration - perfect for active travelers who want to see the Windy City in a fresh and energizing way.
Provider: Viator
Sustainability Score: 9/10 | Hygge Factor: 8/10
2. Chicago Half-Day Bike Rental
Discover the freedom of exploring Chicago on two wheels with a convenient half-day bike rental. Ride along the Lakefront Trail for stunning views of Lake Michigan, or cruise through downtown neighborhoods and parks like Grant Park and Millennium Park. Perfect for sightseeing, photography, or a relaxed adventure, this self-guided experience lets you set your own pace and itinerary. With well-maintained bikes and easy access to Chicago’s top attractions, it’s a fun, sustainable, and flexible way to experience the city’s vibrant atmosphere.
Provider: Viator
Sustainability Score: 9/10 | Hygge Factor: 9/10
3. Chicago Architecture River Cruise
Explore the beauty and innovation of Chicago’s skyline on this expertly narrated architecture cruise along the Chicago River. Led by knowledgeable guides, the tour highlights more than 40 of the city’s most significant buildings, including the Tribune Tower, Willis Tower, and the Merchandise Mart. Learn how Chicago rose from the Great Fire to become a world leader in design and engineering while enjoying unobstructed views from the open-air deck. With its perfect mix of storytelling, history, and scenic calm, this cruise offers both insight and relaxation in the heart of the city.
Provider: Viator
Sustainability Score: 7/10 | Hygge Factor: 8/10
4. Behind-the-Scenes Chicago Pizza Tour
Discover why Chicago is world-famous for its pizza on this guided coach tour dedicated to the city’s most beloved dish. Travel through different neighborhoods to sample a variety of styles - from classic deep-dish to crispy tavern-style - and learn the stories behind each recipe and restaurant. Your expert guide shares fun insights into the city’s pizza history and the local pride that makes each slice unique. With comfortable transportation and plenty of delicious stops, this tour is the perfect combination of flavor, culture, and cozy indulgence.
Provider: Viator
Sustainability Score: 7/10 | Hygge Factor: 8/10
5. Chicago Magnificent Mile Walking Tour
Discover the heart of downtown Chicago on a guided walking tour along the city’s most iconic avenue - the Magnificent Mile. Learn how this bustling stretch of Michigan Avenue became a world-renowned destination for architecture, culture, and shopping. Your expert guide shares fascinating stories about the area’s transformation after the Great Chicago Fire, pointing out historic landmarks such as the Tribune Tower, Wrigley Building, and John Hancock Center. Along the way, enjoy stunning views of the skyline, Lake Michigan, and vibrant street life. This tour offers a perfect mix of history, beauty, and city energy, ideal for first-time visitors or anyone eager to see Chicago up close.
Provider: Expedia
Sustainability Score: 9/10 | Hygge Factor: 9/10
6. Museum of Contemporary Art Chicago
Step into one of the nation’s premier contemporary art museums and experience creativity in its most dynamic form. The Museum of Contemporary Art Chicago (MCA) showcases innovative works across mediums - from painting and sculpture to performance and digital installations - highlighting both established and emerging artists from around the world. Explore ever-changing exhibitions that challenge perspectives and celebrate artistic experimentation. Located near the Magnificent Mile, the MCA offers a modern, welcoming space to reflect, engage, and be inspired. Whether you’re an art enthusiast or a curious visitor, this experience connects you to the pulse of Chicago’s vibrant cultural scene.
Provider: Expedia
Sustainability Score: 9/10 | Hygge Factor: 9/10
7. Chicago Fulton Market Donut Adventure
Treat yourself to a delicious exploration of Chicago’s vibrant Fulton Market neighborhood on this donut-themed walking tour. Led by a local guide, you’ll visit some of the city’s best bakeries and donut shops, sampling a variety of creative and classic flavors along the way. As you stroll through this revitalized industrial district, learn about its transformation into one of Chicago’s top foodie destinations filled with innovation and charm. With plenty of tastings, stories, and cozy café stops, this tour is the perfect mix of indulgence and discovery for travelers who love local flavor and good company.
Provider: Expedia
Sustainability Score: 7/10 | Hygge Factor: 8/10
8. Chicago in a Day: Food, History, and Architecture Tour
Experience the full spirit of Chicago on this immersive full-day tour that captures the city’s flavor, culture, and creativity. Walk through downtown and historic neighborhoods with a local guide who shares stories of the city’s past, from its rebuilding after the Great Fire to its rise as a hub of innovation. Along the way, sample classic Chicago bites like deep-dish pizza and hot dogs, and admire architectural marvels such as the Wrigley Building and Millennium Park. With time for both sightseeing and savoring, this tour perfectly balances learning, tasting, and connecting with the city’s vibrant atmosphere.
Provider: Viator
Sustainability Score: 8/10 | Hygge Factor: 8/10
9. Chinatown History and Culture Walking Tour
Step into one of Chicago’s most vibrant neighborhoods and explore the fascinating history and culture of Chinatown. Led by a knowledgeable local guide, this 2-hour walking tour takes you through colorful streets lined with traditional architecture, family-run shops, and authentic eateries. Learn about the stories of early Chinese immigrants, the symbolism behind the neighborhood’s landmarks, and the community’s enduring influence on Chicago’s identity. With its blend of history, culture, and sensory experiences, this tour offers an intimate and educational glimpse into one of the city’s most unique and welcoming areas.
Provider: Viator
Sustainability Score: 8/10 | Hygge Factor: 8/10
10. Chicago River Architecture Tour
Experience Chicago from a fresh perspective on a guided architecture cruise through the heart of the city. As you glide down the Chicago River, expert guides share the stories behind the city’s most iconic buildings and how Chicago became the birthplace of modern architecture. See landmarks like the Wrigley Building, Marina City, and Willis Tower up close while learning about the innovative designs that shaped the skyline. The calm water, gentle breeze, and dazzling reflections create a cozy yet awe-inspiring experience that captures Chicago’s creative spirit and history.
Provider: Viator
Sustainability Score: 7/10 | Hygge Factor: 9/10
Plan Your Trip to Chicago
Ready to explore Chicago? These experiences represent the best of sustainable, hygge-inspired travel. Each option has been carefully selected for its commitment to environmental responsibility and authentic local experiences.
Remember to travel mindfully, support local businesses, and leave only footprints behind. Safe travels!
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