The 10 Best Tours in Chicago

Chicago, a city renowned for its stunning architecture, vibrant food scene, and rich history, offers an array of tours that promise to immerse you in its unique charm. Whether you’re a foodie, an architecture enthusiast, or a history buff, the Windy City has something fascinating for you.

Here are the 10 best tours in Chicago that will transform your visit into an unforgettable adventure!

90-Minute Chicago River Architecture Tour

Glide along the Chicago River, surrounded by the city’s towering architectural marvels. This 90-minute tour offers a narrative journey through Chicago’s design history, with stories of iconic skyscrapers like Willis Tower and Wrigley Building. It’s a visual treat where architecture tells the tale of a city’s evolution.

Feel the breeze off the river as expert guides recount the architectural triumphs and tribulations of the Windy City. The buildings along the river in Chicago represent the city’s history, starting from the period after the Great Chicago Fire to its transformation into a city known for its tall skyscrapers. This tour invites you into the very soul of Chicago’s rich architectural history.

• Tour Fee: From $44.00
• Schedule: 1 hour 30 minutes
• Inclusions: Free Cancellation, Likely to Sell Out

Chicago Architecture River Cruise

Discover Chicago’s architectural splendors from the water. This hour-long river cruise sails past the city’s most famous buildings, blending stunning views with historical insights. Each building has a story, making this cruise a journey through Chicago’s architectural heritage. It’s a perspective of the city that’s both enlightening and breathtaking.

The cruise offers an intimate encounter with Chicago’s architectural giants, narrated by expert guides. You’ll pass by landmarks like the Tribune Tower and the Willis Tower, learning about their historical significance and the visionaries behind them. This tranquil voyage not only showcases the city’s structural beauty but also delves into the evolution of its urban landscape, making it an indispensable experience for any architecture enthusiast.

• Tour Fee: From $47.00
• Schedule: 1 hour
• Inclusions: Free Cancellation, Likely to Sell Out

Chicago Favorites Ultimate Food & Walking Tour

Indulge in Chicago’s signature dishes on this 3-hour walking tour. Savor deep-dish pizza, Chicago-style hot dogs, and more, while exploring the city’s culinary landscape. This tour is a celebration of Chicago’s rich cultural fabric, woven into its eateries and neighborhoods.

As you walk, your guide will share fascinating stories about Chicago’s history and how it has shaped the city’s food scene. You’ll not only leave with a satisfied appetite but also with a deeper appreciation of Chicago’s heritage. The tour provides a perfect blend of gastronomic excellence and cultural exploration, making it a must-do for anyone wanting to experience the true essence of the Windy City.

• Tour Fee: From $79.99
• Schedule: 3 hours
• Inclusions: Free Cancellation, Likely to Sell Out

Chicago Crime and Mob Bus Tour

Step back in time with the Chicago Crime and Mob Bus Tour. This 47-minute journey takes you through the hangouts of infamous mobsters like Al Capone. It’s a thrilling insight into the city’s gritty past, revealing stories of crime and intrigue at every turn.

This tour not only showcases famous crime scenes but also delves into the lives of the people behind them. The guides’ vivid storytelling paints a picture of a bygone era, making you feel as if you are part of Chicago’s tumultuous past. It’s a unique way to understand the city’s history, far beyond the pages of a textbook.

• Tour Fee: From $46.00
• Schedule: 47 minutes
• Inclusions: Free Cancellation

360 CHICAGO Observation Deck Admission (Hancock Center)

Elevate your Chicago experience literally as you ascend 1,000 feet to the Observation Deck. Here, the city’s architectural magnificence unfolds before your eyes, from the sprawling parks to the shimmering lake. It’s an ideal spot for photographers and sightseers alike, offering a bird’s eye view of the urban tapestry.

Engage with interactive exhibits that delve into Chicago’s rich history and culture. The deck isn’t just a viewing platform; it’s an educational journey. Learn about the city’s landmarks and their stories, adding depth to the stunning visuals. It’s a fusion of sight and insight, making the 360 CHICAGO experience both enlightening and exhilarating.

• Tour Fee: From $30.00
• Schedule: Flexible
• Inclusions: Free Cancellation, Likely to Sell Out

Gangsters and Ghosts Tour in Chicago

Explore the eerie side of Chicago with the Gangsters and Ghosts Tour. This 2-hour walking tour delves into the city’s haunted history and notorious underworld. You’ll be captivated by tales of ghostly sightings and gangster lore, making for a spine-tingling adventure through Chicago’s streets.

Stroll through the darkened streets and alleys where infamous mobsters once ruled with an iron fist. The tour also shines a light on Chicago’s most haunted locations. Hear about the spirits that linger in historic buildings and the mysterious events that led to these ghostly hauntings. Whether you’re a believer in the paranormal or just love a good spine-chiller, this tour offers an intriguing glimpse into Chicago’s ghostly legends.

• Tour Fee: From $35.00
• Schedule: 2 hours
• Inclusions: Free Cancellation

Big Bus Chicago Hop-On Hop-Off Tour

Experience Chicago’s highlights with the flexibility of the Big Bus Hop-On Hop-Off Tour. With 12 stops, you can explore attractions like Navy Pier and Millennium Park at your leisure. The open-top bus and live commentary offer a fun and informative way to see the city.

This tour is ideal for first-time visitors seeking an overview of the city or for returning travelers wanting to delve deeper into specific attractions. The flexibility to hop on and off means you can tailor your day to your interests, spending more time at the sites that intrigue you most. From the Loop to the Lincoln Park, the Big Bus Tour encapsulates the diverse spirit of Chicago.

• Tour Fee: From $48.60
• Schedule: 2 hours
• Inclusions: Free Cancellation

Skydeck Chicago Admission Ticket

Ascend to the Skydeck in Willis Tower for a spectacular view of Chicago. The Ledge, a glass balcony extending outside the 103rd floor, offers a thrilling perspective of the city below. This experience symbolizes Chicago’s towering ambition and spirit. The Skydeck provides an unmatched, sky-high adventure, making you feel as if you’re walking in the clouds above the bustling cityscape.

Capture the essence of Chicago’s urban majesty from this unique vantage point. As you stand on the glass-floored Ledge, the city’s architectural wonders, sprawling parks, and shimmering Lake Michigan unfold beneath you. This awe-inspiring view offers not just a photo opportunity, but a moment to truly appreciate the Windy City’s grandeur and the audacious spirit that built it.

• Tour Fee: From $44.00
• Schedule: Flexible
• Inclusions: Free Cancellation

Chicago’s Chinatown Food and Walking Tour

Immerse yourself in the vibrant atmosphere of Chicago’s Chinatown, a hub of rich cultural and culinary traditions. This 3-hour tour takes you through its colorful streets, bustling markets, and hidden gems. You’ll experience the authentic flavors of Asia, from sizzling Peking duck to delicate dim sum, as each dish tells a story of heritage and tradition.

Beyond the cuisine, this tour offers a deep dive into the history and culture of one of Chicago’s most fascinating neighborhoods. Your knowledgeable guide will share stories and insights about the area’s past and present, weaving a tapestry that connects the food to the people and their traditions. It’s a unique opportunity to engage with the community and understand the heart of Chinatown.

• Tour Fee: From $79.99
• Schedule: 3 hours
• Inclusions: Free Cancellation

Private 45-Minute Chicago Skyline Helicopter Tour

Take off on a luxurious journey that elevates your Chicago experience. From the comfort of your private helicopter, gaze upon the sprawling cityscape, with its gleaming skyscrapers and serene Lake Michigan. This tour gives you a unique vantage point to appreciate the city’s grandeur, away from the bustling streets.

Your pilot personalizes the experience, highlighting iconic sites like Willis Tower, Navy Pier, and Millennium Park. As the city unfolds below, capture unparalleled photos and enjoy intimate moments above Chicago’s vibrant heart. This tour isn’t just sightseeing; it’s a sky-high adventure that caters to your curiosity and sense of wonder.

• Tour Fee: From $849.00 (Per group)
• Schedule: 45 minutes
• Inclusions: Free Cancellation

Chicago is a city of endless exploration, and these tours offer the most vivid and memorable ways to experience it. From the heights of the sky to the depths of its historical streets, each tour promises a unique and enriching adventure. So grab your camera, pack your things, and get ready to discover the heart and soul of Chicago!