Chicago is a city that knows how to show off its best features. Its stunning skyline, centuries-old architecture, and vibrant neighborhoods make it a prime spot for guided tours. Whether you’re into learning about the city’s skyscraper history, sampling local foods, or uncovering its darker past, Chicago offers a variety of experiences that go beyond the usual sightseeing. We particularly like the Chicago River: 1.5-Hour Guided Architecture Cruise because it’s a classic, with a knowledgeable guide and the chance to see the city from its most iconic vantage point. Plus, the option to enjoy local food and drinks onboard makes it a full experience.
This list brings together the most interesting tours in Chicago, from captivating boat rides and walking explorations to food adventures and even spooky ghost hunts. Many are highly rated, and all promise an engaging way to see the city through different lenses.
Quick Overview
Our list includes a variety of Chicago architecture cruises like the Chicago: 1.5-Hour Lake and River Architecture Cruise and the Chicago River: 1.5-Hour Guided Architecture Cruise, designed for those who want to appreciate Chicago’s famous skyline and design innovations. For food lovers, options like the Chicago Walking Food Tour and Chicago Pizza Tour highlight the city’s culinary diversity, with generous tastings from deep-dish to local favorites. If history or thrill-seeking is your style, tours like the Gangsters and Ghosts Walking Tour and Medieval Torture Museum Ticket add a spooky, edgy twist.
Below, you’ll find detailed descriptions of each tour, helping you decide which fits your interests and pace.
1. Chicago River: 1.5-Hour Guided Architecture Cruise
At number 1, this classic Chicago architecture cruise offers a comprehensive 1.5-hour journey along all three branches of the Chicago River. Pre-purchasing tickets means you skip lines and settle into a comfortable spot—either on the outdoor deck or inside a climate-controlled cabin. The tour is led by an engaging, lively guide who explains how Chicago’s skyline became globally renowned, with buildings like the Wrigley Building and Tribune Tower often taking center stage. Guests consistently praise the knowledgeable narration and the full-service cash bar that adds a relaxed vibe. This cruise is perfect if you want a deep yet accessible understanding of Chicago’s architectural evolution. Bottom line: A rewarding, picturesque tour that appeals to both design enthusiasts and first-time visitors alike.
2. Chicago: Architecture River Cruise Skip-the-Ticket Line
Another highly-rated option, this skip-the-line cruise offers the same river journey as the first but with a slightly shorter 75-minute duration. It includes live narration about 40 landmark buildings, making it a great choice for those keen on quick but rich insights. Guests can relax with a drink from the cash bar, soaking in the elegant cityscape while learning about the city’s architectural stories. This tour’s popularity stems from its efficient access and expert docents who keep the commentary lively and informative. It’s ideal if you’re short on time but still want a well-rounded experience. Bottom line: Efficient, insightful, and a great value for architecture lovers pressed for time.
3. Chicago in a Day: Explore Food, History, and Iconic Architecture
This five-hour tour packs in a lot, making it perfect for first-time visitors who want a broad overview. Combining walking, food tastings, and landmark visits, the tour explores the Chicago Riverwalk, Millennium Park, and historic districts, all with a small group of just 12 people max. You’ll get to see Chicago’s skyscrapers and architectural icons like the Chicago Theatre, and enjoy generous bites from deep-dish pizza to Italian beef sandwiches. The guide’s storytelling makes the city’s past come alive, and the small group size ensures personal attention. The reviews highlight its balance of food, sights, and history, with “rich narration” and “ample tastings” that feel like an authentic local experience. Bottom line: An excellent option for those who want a quick but deep dive into Chicago’s culture and cuisine.
4. Chicago: 45-Minute Family-Friendly Architecture River Cruise
Ideal for families, this shorter 45-minute cruise offers a family-friendly commentary and a chance to see some of Chicago’s most famous landmarks. The live narration is tailored to all ages, making it engaging for kids and adults alike. The full-service cash bar is available for adults, but the focus remains on the sights and fun facts that captivate younger travelers. The quick trip ensures even the youngest family members stay interested without long fatigue. Based on reviews, it’s a favorite for those seeking a relaxed yet engaging Chicago experience with children. Bottom line: Smart choice for families wanting a memorable, short boat tour.
5. Chicago: 1.5-Hour Lake and River Architecture Cruise
For those who want a comprehensive view of the city, this cruise combines Lake Michigan and the Chicago River in a 1.5-hour journey. It’s the only cruise that links the lake with the river, passing through the legendary Chicago Lock. The tour features expert local guides who illuminate the city’s architectural secrets while enjoying flexible seating—either outdoor or climate-controlled. Many reviews mention the “full bar” with local beers and Garrett’s popcorn, adding a fun Chicago touch. This cruise is excellent for those interested in both shoreline and river architecture, providing a full picture of the skyline. Bottom line: A fantastic, all-in-one cruise for architecture enthusiasts and first-timers alike.
6. Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
For a completely different experience, this museum tour delves into medieval torture devices and techniques. Covering 6,000 square feet, it features wax sculptures and interactive displays, making it both educational and gruesome. The audio guide adds context, and the ghost-hunting app takes the experience into the spooky realm—perfect for Halloween or thrill-seekers. Visitors comment on its “interactivity” and “creepy, detailed exhibits,” making it a favorite for horror fans and history buffs who enjoy the macabre side of Chicago’s past. Bottom line: A dark, fascinating experience that’s as gruesome as it is informative.
7. Chicago Walking Food Tour With Secret Food Tours
This three-hour walking tour combines Chicago’s food scene with sightseeing in the Loop. Passing landmarks like the Chicago Public Library and the Chicago River, it offers an authentic taste of the city’s culinary traditions. You’ll sample deep-dish pizza, Italian beef sandwiches, and local specialties, enough for a full meal. The small group size (max 12) ensures lively conversation, and the guide shares stories behind the food and architecture. Guests love the “well-paced” itinerary and “fantastic food,” making it ideal for those wanting a culinary adventure with cultural context. Bottom line: Perfect for foodies who want to explore on foot and learn about Chicago’s flavors.
8. Chicago: Gangsters and Ghosts Guided Walking Tour
This two-hour walk explores Chicago’s darker history—from notorious gangsters like Al Capone to ghost stories around historic landmarks. The guide provides insider knowledge about the city’s crime scene and eerie tales of haunted sites like the Congress Hotel. It’s a fun, atmospheric tour for those interested in Chicago’s criminal past and ghostly legends. The reviews mention “entertaining” stories and a good balance of history and mystery. It’s especially suitable for evening entertainment. Bottom line: A lively tour for fans of crime stories and ghost lore.
9. Chicago City Tour with Architecture River Cruise Option
This flexible tour combines bus sightseeing with the option to upgrade to a boat tour. It hits major spots like Millennium Park, the Bean, and the Buckingham Fountain, with a small-group experience. The optional river cruise allows for a more detailed look at Chicago’s architecture, ideal if you want a broad overview with the flexibility to customize. Reviewers praise the “personalized” approach and “easy hotel pick-up,” making it convenient. It’s perfect for travelers who want a comprehensive view and the option to add the river tour. Bottom line: Versatile, well-rounded sightseeing with upgrade potential.
10. Bikes, Bites, and Brews: Chicago’s Signature Dishes Bike Tour
This half-day biking tour takes you through neighborhoods like Lincoln Park, Wrigleyville, and Gold Coast, sampling Chicago’s iconic foods—deep-dish pizza, hot dogs, and local craft beers. Covering about 13 miles at a moderate pace, it’s great for active travelers who want to combine exercise with food. Guides share fun facts about the city’s culture and history along the way. Reviewers mention “endless stories” and “good balance of riding and eating.” It’s an excellent choice for those who want to see many neighborhoods without missing out on local flavors. Bottom line: A lively, active way to experience Chicago’s culinary and neighborhood diversity.
11. Chicago: 360 CHICAGO Observation Deck Ticket
Offering one of the best panoramic views, this 94-story observation deck lets you skip the ticket line. The elevator whisks you up in 40 seconds, delivering stunning lake and skyline vistas, including views of four states. The deck’s interpretive exhibits help you learn about Chicago’s architecture and neighborhoods. It’s a straightforward, no-fuss experience for those wanting a quick, memorable photo op. Reviewers mention “breathtaking views” and the convenience of skipping long lines. It’s perfect for travelers, families, or anyone wanting a short but spectacular view of the city. Bottom line: A must-do for skyline lovers with limited time.
12. Chicago Murder Mystery Tour
This interactive walking experience turns sightseeing into a game, with players solving a fictional murder case set in Chicago neighborhoods. It includes costumes and souvenir mugshots, giving it a fun, immersive twist. Covering popular sites like Water Tower Place and Oak Street Beach, it combines history, mystery, and humor. Reviewers say it’s “entertaining” and a good way to explore different districts. It’s best suited for groups looking for a lighthearted, participatory experience. Bottom line: A playful alternative to traditional tours, ideal for families or friends.
13. 2-Hour Guided Segway Tour of Chicago
For a fun, active way to cover lots of ground quickly, this guided Segway tour takes you through Millennium Park, the Buckingham Fountain, and the Museum Campus. With training included, even beginners will feel confident. The small group (max 8 people) ensures a personal experience, and the guide shares colorful stories about Chicago’s landmarks. Reviewers highlight the “awesome guide” and the “fun way” to see the city. It suits travelers who want a hands-on, memorable sightseeing experience without the fatigue of walking. Bottom line: A unique, lively way to explore with a small group.
14. Chicago’s Chinatown Food and Walking Tour
This three-hour tour takes you through Chicago’s Chinatown, sampling dishes from dim sum to Sichuan cuisine. It includes visits to local restaurants and cultural landmarks like the Pui Tak Center. The guide shares stories about the neighborhood’s history and culinary influences, making it both a food and cultural experience. Guests mention “generous portions” and “friendly guides,” making it a favorite for food lovers eager to avoid tourist traps. Perfect if you want an authentic taste of Chicago’s Asian community. Bottom line: Delicious, cultural, and personable—ideal for fans of Asian cuisine.
15. Chicago Night Crimes Tour by Bus
This two to two-and-a-half-hour evening bus tour explores Chicago’s crime history, spotlighting Al Capone, Bugs Moran, and infamous scenes like the St. Valentine’s Day Massacre. The guide shares colorful stories while you ride past landmarks like Harry Caray’s and the John Hancock Center. It’s a lively way to learn about the city’s less glamorous side, with a focus on mobsters and mysterious incidents. Reviewers note the “entertaining stories” and “great guide,” making it a fun, atmospheric evening activity. Best suited for history buffs or those curious about Chicago’s notorious past. Bottom line: A captivating, evening tour for crime fiction fans and night owls.
16. Chicago Pizza Tour
Finally, the Chicago Pizza Tour is a three-and-a-half-hour guided bus experience exploring neighborhoods famous for their pizza. Visiting spots like Pizano’s and Pequod’s, it offers samples of deep-dish, thin crust, and coal-fired pies. The tour includes historical commentary on Chicago’s pizza culture, with enough tasting to satisfy a pizza lover’s craving. Guests rave about the “fun guide” and “diverse pizza styles,” making it a must for foodies eager to understand Chicago’s culinary identity. It’s great for those who want a relaxed, tasty exploration that can double as a meal. Bottom line: A delicious journey through Chicago’s pizza heritage.
How to Choose the Right Chicago Tour for You
Selecting the perfect tour depends on your interests, timeframe, and energy level. If architecture is your main focus, the Chicago River: 1.5-Hour Guided Architecture Cruise offers an in-depth look with stunning views. For a quick scenic overview, the Chicago: 45-Minute Family-Friendly Architecture River Cruise is perfect for families or those with limited time. Foodies should consider the Chicago Walking Food Tour or the Chicago Pizza Tour, both providing generous tastings and local insights. History or thrill-seekers might enjoy the Gangsters and Ghosts or Medieval Torture Museum, which add an interactive, spooky edge.
Practical tips: book early for popular boat and food tours, especially in summer or during special events. Consider your physical fitness—bike, Segway, and walking tours vary in activity level. If you want a flexible experience, the Chicago City Tour with Architecture River Cruise lets you combine different modes of exploration.
Final Thoughts
Chicago offers a wide range of tours, each highlighting a different facet of the city’s vibrant personality—from its soaring skyscrapers and lakefront vistas to its flavorful foods and mysterious past. For a classic experience, the architecture cruises like the Lake and River Architecture Cruise give you unbeatable views and fascinating stories. Food lovers will adore the Chicago Pizza Tour, which covers the city’s rich pizza traditions, while history buffs might prefer the Gangsters and Ghosts Walking Tour for its thrilling tales.
No matter your style, booking early ensures you won’t miss out, especially during peak months. Use this guide to pick the experience that will make your Chicago trip unforgettable and get ready to enjoy all the city has to offer.