Chicago’s most rewarding tours fall into three main categories, each offering a distinct look at this magnificent city. The Chicago Crime and Mob Bus Tour stands out for its no-nonsense exploration of Al Capone’s era, bringing 1920s gangster history to life through real locations. History buffs will appreciate the Chicago River Architecture tour – a 90-minute journey showcasing the city’s architectural evolution through more than 50 stunning buildings. For food lovers, the Chicago Favorites Food Walking Tour hits all the right spots, featuring deep-dish pizza, Chicago dogs, and Italian beef in authentic neighborhoods.
Let’s explore these top-rated tours in detail.
Key Points
- Chicago offers a diverse range of tours, from crime and history tours to architectural and culinary experiences, catering to various interests and budgets.
- The Gangsters and Ghosts Walking Tour and the Chicago River 90-Minute History and Architecture Tour are highly rated, with over 7,000 participants and a 92% traveler recommendation, respectively.
- Culinary tours, such as the Chicago Favorites Ultimate Food and Walking Tour, provide opportunities to sample the city’s signature dishes, including deep-dish pizza and Chicago-style hot dogs.
- Customizable private tours, like the Private Custom City Tour, offer personalized experiences with knowledgeable guides and flexible itineraries based on individual preferences.
- Tour options cater to different accessibility needs, with some being wheelchair-accessible and accommodating strollers, ensuring a inclusive experience for all travelers.
Chicago Crime and Mob Bus Tour
Although located in the heart of downtown Chicago, the Chicago Crime and Mob Bus Tour transports guests back in time to the city’s notorious gangster past.
With a 90% recommendation rate from over 2,700 travelers, this 2-hour luxury coach tour is a must-do activity for anyone interested in Al Capone, The Untouchables, and other infamous figures from Chicago’s criminal underworld.
Guests will explore key locations, including the Biograph Theatre, Holy Name Cathedral, and the site of the St. Valentine’s Day Massacre, while an experienced guide shares thrilling stories.
The tour also includes access to a mini mob museum and historic video footage, as well as photo opportunities at crime scenes.
While not wheelchair accessible, the tour is stroller-friendly and welcomes service animals.
Travelers should arrive 15 minutes early, as the bus departs on time, and a $5 per person gratuity is recommended.
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Chicago: Customizable Private Chicago Scenic Driving Tour
Seeking a personalized sightseeing experience in Chicago? Consider the Customizable Private Chicago Scenic Driving Tour.
This 2-hour tour allows you to explore the city’s iconic landmarks and attractions at your own pace. Starting from $315 per group (up to 3 participants), the tour includes hotel pickup and drop-off, private transportation, and a knowledgeable guide.
The itinerary features must-see spots like Millennium Park, Wrigley Field, and the Museum Campus, with the flexibility to tailor the tour to your interests.
Enjoy scenic views of the city skyline and Lake Michigan, and stop for photo opportunities at sites like the Chicago Cultural Center’s Tiffany stained-glass dome.
With free cancellation up to 24 hours in advance and a 5/5 rating from previous travelers, this tour is an excellent way to discover Chicago’s highlights.
Don’t miss your chance to secure your spot, as this tour is likely to sell out quickly.
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Chicago: Gangsters and Ghosts Walking Tour
Explore Chicago’s notorious history of gangsters and ghosts on the captivating Chicago: Gangsters and Ghosts Walking Tour. This highly-rated 95% tour takes you through Chicago’s dark past, from the Roaring Twenties to present-day hauntings.
Over 7,000 travelers have enjoyed this immersive experience, which has earned a Badge of Excellence.
Led by expert historians, the 2-3 hour walking tour visits iconic sites like the Palmer House, Congress Hotel, and Death Alley. Along the way, you’ll uncover the stories of infamous figures like Al Capone and hear chilling ghost tales.
The moderate fitness required is well worth it for this engaging and informative look into Chicago’s gritty history.
While the base tour is a walking experience, an optional minibus upgrade is available. Reviewers suggest the tour could be enhanced with the use of headsets, especially in noisier areas.
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Chicago: Milwaukee Harley-Davidson Museum & Brewery Day Tour
The Chicago: Milwaukee Harley-Davidson Museum & Brewery Day Tour offers an engaging exploration of Milwaukee’s renowned motorcycle and brewing heritage. Priced at $125 per person, this 1-day tour departs from Millennium Park in Chicago and includes round-trip transportation.
Visitors can enjoy the history of Harley-Davidson bikes at the museum, learning about the company’s evolution since 1903. The tour also features a visit to the iconic Miller Brewery, where guests can sample the company’s famous beers and discover its brewing legacy.
In between these attractions, the tour allows time to explore the vibrant Milwaukee Public Market, showcasing the city’s diverse culinary offerings.
Though admission fees to the Harley-Davidson Museum and Miller Brewery are optional, the tour provides a seamless, hassle-free experience. With a 5/5 rating based on customer reviews, this day trip is an excellent choice for anyone seeking to uncover Milwaukee’s rich cultural and industrial heritage.
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Chicago River 90-Minute History and Architecture Tour
A popular sightseeing option for visitors to Chicago is the Chicago River 90-Minute History and Architecture Tour.
With over 7,197 reviews and a 92% traveler recommendation, this tour covers more than 130 years of the city’s architectural history.
Travelers can view iconic structures like the Willis Tower and Merchandise Mart while gliding past landmarks like the Chicago Water Tower and Marina City.
The narrated tour is led by professional guides and offers both indoor and outdoor seating.
Restroom facilities are available on board, and alcoholic beverages, drinks, and snacks can be purchased.
The tour can accommodate up to 300 travelers and concludes at the starting point on Michigan Avenue.
Reviewers praise the tour’s safety, informative guides, and scenic views, suggesting visitors sit on the upper deck or right side for the best experience.
Whether visiting in winter or summer, this architecture tour provides a hassle-free way to see Chicago’s top attractions.
Read our full review: Chicago River 90-Minute History and Architecture Tour Review
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Chicago Highlights Private Walking Tour With A Guide
Visitors seeking a personalized introduction to Chicago’s architectural wonders can embark on a 2-hour Chicago Highlights Private Walking Tour with a knowledgeable local guide.
This private tour offers an exclusive experience, allowing guests to customize the itinerary to their interests. The tour starts at the iconic LondonHouse Chicago, with optional stops at landmarks like the Wrigley Building, Palmer House Hilton, Carbide and Carbon Building, and Reliance Building, before concluding at the Chicago Cultural Center.
Along the way, the guide provides insightful commentary on the city’s rich history and architectural evolution. Guests can enjoy photo opportunities and guided tours, with the flexibility to explore at their own pace.
The tour is wheelchair accessible, and the cancellation policy offers free cancellation up to 24 hours in advance for a full refund. Visitors can also receive valuable recommendations for additional activities to enhance their Chicago experience.
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Chicago Lake and River Architecture Tour
For those seeking a more comprehensive architectural tour of Chicago, the Chicago Lake and River Architecture Tour offers a captivating 90-minute experience.
With over 2,000 reviews and a 93% traveler recommendation, this tour has earned a prestigious Badge of Excellence. Passengers will enjoy scenic views of the Chicago skyline along Lake Michigan’s 26-mile shoreline, as well as live commentary from knowledgeable local guides.
The tour includes 45 minutes on the Chicago River and 45 minutes on Lake Michigan, providing a well-rounded exploration of the city’s architectural marvels.
Travelers can take advantage of climate-controlled indoor and outdoor seating, a restroom on board, and the opportunity to purchase snacks and drinks.
While the tour isn’t wheelchair accessible, service animals are allowed, and it’s easily accessible via public transportation.
With an average rating of 4.7 out of 5, the Chicago Lake and River Architecture Tour is praised for its informative guides, breathtaking views, and engaging historical insights, making it a must-do activity for visitors to the Windy City.
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Chicago : Loop Private Walking Tour With a Guide
Enjoy the architectural wonders and rich history of Chicago’s iconic Loop district on this private walking tour. Led by a knowledgeable local guide, you’ll explore the area’s stunning buildings, from the neo-gothic Tribune Tower to the iconic Art Deco Carbide and Carbon Building.
Along the way, you’ll learn about the city’s fascinating past, from its humble beginnings to its rise as a global economic powerhouse.
Stroll through Millennium Park, home to the famous Bean sculpture, and marvel at the futuristic design of the Jay Pritzker Pavilion.
Explore the legacy of the Great Chicago Fire and its impact on the city’s architecture. Discover hidden gems, like the historic Rookery Building and the intricate mosaics of the Chicago Theater.
This personalized experience allows you to tailor the tour to your interests, ensuring an enriching and memorable exploration of Chicago’s architectural and cultural heart.
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Chicago Favorites Ultimate Food and Walking Tour
This immersive food tour takes travelers on a delectable journey through Chicago’s iconic culinary landscape. Rated 4.8 stars from over 1,400 reviews, the Chicago Favorites Ultimate Food and Walking Tour offers a well-rounded experience highlighting the city’s most beloved dishes.
Guests can expect to savor deep-dish pizza, Chicago-style hot dogs, an Italian beef sandwich, and the original brownie during the 1.5-mile walking excursion.
The tour also provides an opportunity to explore Chicago’s architecture, cultural history, and scenic promenades, with the option to rent a bike or kayak during warmer months. For colder weather, the tour utilizes the Chicago Pedway for comfort.
With a maximum group size of 16, travelers can enjoy personalized attention from the knowledgeable, English-speaking guide. Dietary accommodations are available, and the tour operates rain or shine.
Priced starting at $84.99 per person, this tour is a must for any foodie visiting the Windy City.
Read our full review: Chicago Favorites Ultimate Food and Walking Tour Review
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Chicago: Full-Day Guided City Tour by Bus
Embarking on the Chicago: Full-Day Guided City Tour by Bus, travelers will embark on an immersive exploration of the Windy City’s iconic landmarks and hidden gems. Priced at $132 per person, this comprehensive, full-day tour departs from the Millennium Park Welcome Center and is conducted in English.
With free cancellation up to 24 hours in advance, the tour offers the flexibility to plan ahead.
Throughout the day, guests will visit must-see attractions like Millennium Park, Grant Park, and the Chicago Water Tower. Optional add-ons include the Art Institute of Chicago, 360 Chicago, and an architectural boat tour, each with varying admission fees.
The tour includes round-trip transportation, a driver and guide, and all taxes and fees.
Travelers should note the tour’s suitability requirements, including the need for a passport or ID card and no wheelchair accessibility.
Weather-related cancellations or adjustments may occur, with alternative dates or refunds offered as needed.
This guided city tour provides an efficient and enjoyable way to experience the best of Chicago in a single day.
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Chicago River 45-Minute Architecture Tour From Magnificent Mile
Travelers can enjoy a 45-minute Chicago River architecture tour that departs from the Magnificent Mile. This highly-rated tour showcases the city’s iconic landmarks and rich architectural history.
With a 92% recommendation rate from 1,948 reviews, the tour earns a 4.7/5 rating based on traveler feedback.
The tour highlights key sights, including the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Guides provide live commentary on the city’s architecture and history, making the experience educational and engaging for all ages.
Passengers can choose between an open-air top deck or a sheltered bottom deck, with amenities like a restroom, climate-controlled lounge, and refreshments available.
The tour departs from 400 N Michigan Ave and returns to the same location. While no parking is available on-site, advance booking is recommended.
Accessibility features include stroller access, though the tour isn’t wheelchair-friendly. This architecture tour offers an excellent way to discover Chicago’s iconic landmarks from the river.
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Chicago: Food Tour on Devon Avenue
Venture into the vibrant cultural tapestry of Chicago’s Devon Avenue, where a delectable food tour awaits.
For $125 per person, this 3-hour guided experience takes you on a mouthwatering journey through the neighborhood’s diverse culinary landscape. Limited to just 10 participants, you’ll explore over 300 restaurants, savoring large-portioned meals at Ghareeb Nawaz and indulging in traditional South Indian desserts at Tahoora Sweets & Bakery.
Enjoy the rich Jewish heritage at Kol Tuv Kosher Foods and discover the world’s largest Indian supermarket chain, Patel Brothers. Along the way, you’ll gain insights into the local customs and cultural practices from passionate food vendors.
With free cancellation up to 24 hours in advance and flexible booking, this tour offers a versatile and unforgettable culinary adventure amidst the vibrant diversity of Chicago’s Devon Avenue.
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Chicagos Delicious Donut Adventure With Underground Donut Tour
The Underground Donut Tour in Chicago offers a delicious adventure for donut enthusiasts. With 1,196 reviews and a 99% traveler recommendation, this tour celebrates Chicago’s best donuts, including tastings at top shops like Doughnut Vault and Do-Rite Donuts & Chicken.
The 2-hour tour explores the Loop neighborhood, offering a variety of donut styles, from glazed to cream-filled. Vegan, gluten-free, and nut-free options are available, catering to diverse dietary needs.
Guided by enthusiastic hosts like Nick, Jackson, and Max, the tour provides a fun and informative experience, blending donut tastings with Chicago’s history. Guests consistently praise the tour’s social aspect and memorable moments.
Priced at $65 per person, the tour offers a free cancellation policy and a money-back guarantee if not satisfied. With a maximum of 20 travelers, the tour is wheelchair and stroller accessible, making it a family-friendly activity suitable for all ages.
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Chicago in a Day: Food and Architecture Private Walking Tour
Although Chicago is renowned for its impressive architecture and bustling food scene, experiencing both aspects in a single day can be a daunting task.
The “Chicago in a Day: Food and Architecture Private Walking Tour” offers a comprehensive solution. The 5-hour private tour, priced at $272.50 per person, covers downtown Chicago’s iconic landmarks and showcases the city’s culinary delights.
Guests will explore the picturesque Chicago Riverwalk, visit Millennium Park, and savor heritage cuisine in the Central Loop. The tour includes a variety of food samples, including deep-dish pizza, sandwiches, and loaded hot dogs, providing a well-rounded taste of Chicago’s renowned food culture.
A local English-speaking guide will share the history and significance of these culinary staples.
With wheelchair accessibility, free cancellation, and the option to reserve now and pay later, this private tour caters to the needs of modern travelers seeking an immersive experience in Chicago’s architectural and gastronomic wonders.
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Chicago in a Day: Food, History and Architecture Walking Tour
What better way to experience the vibrant heart of Chicago than the comprehensive “Chicago in a Day: Food, History and Architecture Walking Tour”? This 5-hour outing covers 3-4 miles, showcasing the city’s iconic landmarks, rich history, and tantalizing cuisine.
Capped at 12 travelers, the tour offers a personalized, informative experience led by passionate local guides.
Dive into Chicago’s cultural heritage with stops at the Chicago Riverwalk and Millennium Park. Learn about the city’s Prohibition-era legacy and architectural wonders.
The culinary journey is equally impressive, featuring deep-dish pizza, Italian beef sandwiches, Chicago-style hot dogs, and popcorn. Vegetarian options are available, though other dietary needs can’t be accommodated.
Accessibility is a priority, with the tour being wheelchair-friendly and child-friendly. Regardless of weather, the experience goes on, making it a practical choice for visitors.
With a 4.9-star rating and 98% recommendation rate, this tour is a must for anyone seeking an immersive exploration of Chicago’s vibrant culture and flavors.
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Chicago: Oktoberfest Malt Row Walking Brewery Tour
Experience the vibrant beer culture of Chicago’s Malt Row on the Oktoberfest Walking Brewery Tour. This 2-hour guided tour takes you through the heart of this bustling brewery district, showcasing the city’s thriving craft beer scene.
Explore local breweries and sample a variety of beers, from classic lagers to innovative seasonal offerings. Learn about the history and brewing process behind each unique brew as you sip and savor.
The tour also includes an Oktoberfest-themed tasting flight, allowing you to fully learn about the festive atmosphere.
Beyond the beer, you’ll discover the architecture and history of the Malt Row neighborhood, once a hub for malt production. Your knowledgeable guide will provide insights into the area’s transformation into a craft beer destination.
Whether you’re a beer enthusiast or simply looking to experience Chicago’s vibrant culture, this Oktoberfest walking tour is a must-do activity.
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Chicago River Architecture Tour With Small Boat Upgrade Option
Discover the architectural wonders of Chicago from a unique perspective on the Chicago River Architecture Tour. This highly-rated tour immerses you in the city’s iconic skyscrapers, landmarks, and design movements.
With 817 reviews and a 94% recommendation rate, this is a must-do activity for architecture enthusiasts and anyone seeking a fresh view of the Windy City.
The tour offers a choice between a standard walking tour or an upgraded small boat experience, allowing you to explore the Chicago River up close. Along the way, you’ll learn from a knowledgeable local guide and enjoy included refreshments.
The tour covers key sights like Navy Pier and the famous “Bean” sculpture, providing insights into the forces that have shaped Chicago’s impressive skyline.
Whether you choose the walking tour or the small boat upgrade, this Chicago River Architecture Tour promises an engaging and memorable journey through the city’s architectural legacy.
With free cancellation and accessible options, it’s a flexible and inclusive way to discover the best of Chicago’s dynamic design.
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Chicago: Icons Guided Architecture Walking Tour
Travelers seeking an immersive exploration of Chicago’s iconic architecture can embark on the “Chicago: Icons Guided Architecture Walking Tour.” This 1.5-hour excursion guides participants through the city’s renowned landmarks, showcasing a range of architectural styles from the 19th century to the present day.
Priced at $30 per person, the tour includes visits to seven notable buildings designed by renowned architects like Frank Gehry, Renzo Piano, and Adrian Smith. Throughout the experience, guests will learn about the historical context and design elements of each structure, culminating at the world-class art and architecture of Millennium Park.
The tour is led by certified professionals and includes admission to the Chicago Architecture Center’s galleries. Booking is flexible, with the option to reserve now and pay later.
Wheelchair accessibility and a 24-hour cancellation policy for a full refund add to the convenience. Reviews praise the knowledgeable guides and engaging experiences, making this tour a must for architecture enthusiasts visiting Chicago.
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Chicago Evening Crime Tour by Bus
This 2.5-hour Chicago Evening Crime Tour by Bus allows guests to explore the city’s notorious criminal past.
Exploring the lives of infamous mobsters like Al Capone and Bugs Moran, the tour visits iconic crime scenes and landmarks associated with Chicago’s Prohibition-era underworld. Guests will see the site of the infamous St. Valentine’s Day Massacre and the Enforcer’s Safe, as well as landmarks like The Burwood Tap and Biograph Theater.
Aboard a luxury coach, guests enjoy live narration by a professional guide, historic video footage, and a keepsake brochure.
The tour also includes exclusive access to a crime quiz. While there are no restroom breaks or eating/drinking allowed on the bus, guests can look forward to photo opportunities at the various sites and an optional deep dish pizza after the tour.
With a maximum of 39 travelers, this immersive experience is great for crime history enthusiasts seeking an engaging and educational night out in Chicago.
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Chicagos Modern Skyscrapers Guided Walking Tour
Chicago is renowned for its modern architecture, particularly during the mid-20th century. Visitors can explore the city’s iconic modern skyscrapers on a 1.5-hour guided walking tour. Priced at Kč 717 per person, the tour focuses on the skeleton frame modern skyscraper, a product of mass production.
Participants will learn about influential architects like Ludwig Mies van der Rohe, Bertrand Goldberg, and Harry Weese, and visit key sites such as the Reliance Building, Marina City, Daley Center, and IBM Building.
The tour also includes a walk along the Chicago River’s new Riverwalk, where guests can enjoy views of the modern structures lining the waterfront.
The tour is wheelchair accessible and led by English-fluent guides. Ticket purchases support the Chicago Architecture Center’s educational initiatives.
Guests should dress appropriately and wear comfortable shoes, as the tour operates rain or shine.
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Bikes, Bites, and Brews: Chicagos Signature Dishes Bike Tour
Cyclists and foodies alike can embark on a delectable journey through Chicago’s most iconic culinary destinations on the Bikes, Bites, and Brews: Chicago’s Signature Dishes Bike Tour.
This half-day tour covers approximately 13 miles (21 km), showcasing the city’s vibrant neighborhoods, from Wrigleyville to the Gold Coast. Travelers will be treated to samples of Chicago’s signature dishes, including hot dogs, deep-dish pizza, and craft beer.
Led by expert local guides, the tour provides historical and cultural insights into the origins of these beloved specialties. Rated 99% recommended by travelers, the tour accommodates a maximum of 16 participants and is suitable for most fitness levels.
With inclusions like bicycles, helmets, and food and drink samples, the tour offers a unique and immersive way to explore Chicago’s rich culinary heritage. Highly praised for its engaging guides and memorable experiences, this tour is a must-do for anyone seeking to discover the city’s iconic flavors.
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Chicago: Elevated Architecture Walking Tour
Embarking on the Chicago: Elevated Architecture Walking Tour, visitors can explore the city’s renowned buildings and infrastructure from a unique vantage point. Priced at Kč 861 per person, this 2-hour tour takes guests through the Loop, passing hundreds of structures while providing narration on their architectural significance.
Riding the iconic “L” transit system, participants gain a rare perspective from over 20 feet above ground, admiring details often missed at street level. The tour includes admission to the Chicago Architecture Center galleries, enriching the experience with the history and impact of the city’s transportation network.
Limited to just 10 participants, the tour offers an intimate setting for learning. With a live English-speaking guide, guests can ask questions and delve deeper into Chicago’s architectural wonders.
Supported by community initiatives, the tour contributes to local education programs and engagement projects.
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Chicago Private Custom City Tour With Hotel Pick up
For those seeking a personalized exploration of Chicago, the Chicago Private Custom City Tour With Hotel Pick up provides a unique and convenient way to experience the city’s top attractions.
Recommended by 98% of travelers and boasting a stellar 4.9-star rating from 191 reviews, this private driving tour is led by knowledgeable guides who share the history and highlights of landmarks like the Lincoln Park Conservatory, Millennium Park, and Museum Campus.
With flexible scheduling and the option to customize stops based on your group’s interests, the tour offers a tailored experience even for repeat visitors.
Accessible for infants and wheelchair users, the tour includes round-trip transit from downtown hotels and free cancellation up to 24 hours prior.
At $539 per group of up to 5 people, this private tour delivers exceptional value and convenience for those looking to make the most of their time in the Windy City.
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Chicago: Tiffany Art Glass Works Walking Tour
Visitors can join the Chicago: Tiffany Art Glass Works Walking Tour to explore the city’s impressive collection of Tiffany art glass installations. Priced at $3,000 per person, the 1.5-hour walking tour is limited to 10 participants and operates in English.
The tour departs from the North lobby of the Chicago Cultural Center, providing easy access to notable locations showcasing Tiffany’s work.
During the tour, guests will compare Tiffany glass with contemporary art-glass installations and learn about Louis Comfort Tiffany’s life and work from an expert guide. The experience also includes admission to the Chicago Architecture Center galleries.
With flexible reservations and free cancellation, travelers can book their spot and pay later. Reviews highlight the tour’s informative and engaging nature, making it a must-do for art enthusiasts visiting Chicago.
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Chicago Lakefront and Museum Campus Small-Group Segway Tour
Travelers who want to explore Chicago’s iconic lakefront and Museum Campus can join the small-group Segway tour. This 2-hour experience showcases the city’s top landmarks, including Buckingham Fountain in Grant Park and stunning views of the skyline along Lake Michigan.
With a maximum of 8 participants, the tour offers a personal and intimate sightseeing adventure. Guided by a professional, the tour includes Segway training and safety equipment. Participants must be at least 12 years old, weigh between 100-260 lbs, and have moderate physical fitness to stand unassisted and ascend stairs.
While not wheelchair-accessible, the tour is suitable for first-time Segway riders, with high ratings for the guides’ training and entertainment. For $65 per person, travelers can efficiently see multiple sights in a short time, perfect for those new to Chicago.
The tour departs from a central location and returns to the starting point, with food and drinks not included. This Segway tour provides an enjoyable and informative way to experience the city’s lakefront and Museum Campus highlights.
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The Sum Up
Chicago offers a wide range of tours that cater to various interests, from crime and mob history to architecture and art glass. Whether you’re looking for a guided walking tour, a scenic driving experience, or a Segway adventure, there’s something for all in this vibrant city. With so many options, you’re sure to find the perfect tour to suit your preferences and make the most of your time in Chicago.