Chicago’s best guided tours cut through the tourist confusion and get right to the city’s essential sights. The classic architecture boat cruise stands out as a must-do, offering the perfect blend of expert commentary and stunning views along the river. Downtown’s 2-hour Segway tours work surprisingly well, efficiently covering major landmarks while keeping groups small. Art Institute guided tours are worth the extra cost, helping visitors navigate this world-class museum’s massive collection. For those who prefer independence, the self-guided gangster history audio tour delivers great value and flexibility. Let’s explore our favorite guided experiences in the Windy City.
Good To Know
- Guided Segway tours of Chicago’s top landmarks like Millennium Park and Buckingham Fountain offer personalized experiences with knowledgeable guides.
- Exclusive museum tours provide skip-the-line access and in-depth explorations of the Art Institute and Field Museum’s natural history exhibits.
- Unique river and cocktail tours showcase Chicago’s iconic architecture while offering complimentary refreshments on historic boats.
- Self-guided tours, including those focused on Chicago’s notorious history and dark side, provide immersive experiences at the visitor’s own pace.
- Artistic and musical tours, such as the Ragtime & Jazz Eras Tour and Art of a City Tours, highlight the city’s rich cultural and artistic heritage.
2-Hour Guided Segway Tour of Chicago
Take a spin on a Segway for a 2-hour guided tour of Chicago’s top landmarks.
This highly-rated tour, recommended by 95% of travelers, takes you through the city’s must-see sights, including Millennium Park, Buckingham Fountain, and Museum Campus.
Led by knowledgeable guides, you’ll learn fascinating insights into Chicago’s history and culture.
The small-group format ensures personalized attention, and Segway training and safety gear are provided.
With 421 reviews and a Badge of Excellence, this tour offers a fun and unique way to explore the Windy City.
Priced from $65 per person, it’s a great value, and you can take advantage of free cancellation up to 24 hours in advance.
Read our full review: 2-Hour Guided Segway Tour of Chicago Review
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Skip-the-Line Art Institute of Chicago Exclusive Guided Museum Tour
For those seeking a more in-depth exploration of Chicago’s renowned Art Institute, the Skip-the-Line Art Institute of Chicago Exclusive Guided Museum Tour offers a captivating and efficient experience.
Boasting a 5-star rating and 99% traveler recommendation, this 2.5-hour tour provides skip-the-line access to the museum’s extensive collection.
Led by knowledgeable and engaging guides, the small group size of 8 people or less ensures personalized attention.
Highlights include the expertise of guides like Ben, Mandy, and Spiro, who are praised for their exceptional art history knowledge and storytelling abilities.
With wheelchair accessibility and proximity to public transportation, this tour is a must for art enthusiasts visiting Chicago.
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Guided Historic Small Boat River Architecture Tour in Chicago
Exploring Chicago’s renowned architecture from the vantage point of a historic wooden yacht, the Chicago River Architecture Tour captivates visitors with its informative and visually stunning experience.
Rated 4.9 out of 5 stars, this top-rated tour takes guests along the Chicago River, showcasing iconic landmarks like the Wrigley Building and Michigan Avenue Bridge.
With knowledgeable guides providing insightful commentary, guests can relax and enjoy complimentary refreshments while taking in the city’s breathtaking skyline.
Despite some feedback on the fast-paced narration and lack of shade, the tour’s smaller boat size, accessibility, and overall positive reviews make it a must-do for architecture enthusiasts visiting Chicago.
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Chicago Guided Cocktail Cruise Tour
Aboard the historic waterways of Chicago, the Chicago River Cocktail Cruise invites visitors to indulge in a captivating blend of architectural marvels and libations.
With a maximum capacity of 150 passengers, this tour offers a badge of excellence and a free cancellation option up to 24 hours prior.
Onboard, guests can enjoy restroom facilities, one or two complimentary alcoholic drinks, and additional beverages and snacks available for purchase.
The cruise departs from and returns to the End of The Ogden Slip dock, providing stunning views and informative narratives from knowledgeable guides.
While some found the experience heavier on architecture than cocktails, the majority praised the service, comfort, and overall enjoyment of this unique Chicago adventure.
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Chicago Self-Guided Audio Tour
The Chicago Self-Guided Audio Tour invites travelers to embark on a captivating exploration of the city’s iconic landmarks and hidden gems at their own pace.
With a private access link to audio guides for 15 attractions, explorers can tailor their journey using the provided itinerary map and interactive Google My Maps interface.
The tour’s flexibility allows users to choose their starting and ending points, plan routes in advance, and experience the city at their desired rhythm.
While the tour isn’t wheelchair accessible, most travelers can participate.
With regular content updates and a complimentary premium version for past dissatisfied customers, the Chicago Self-Guided Audio Tour offers an immersive and personalized sightseeing experience.
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Private Chicago Tour With Driver and Tour Guide. Hotel Pick up Included
For travelers seeking a comprehensive and personalized exploration of Chicago, the Private Chicago Tour with Driver and Tour Guide offers an immersive experience.
Lasting 4 hours, this private tour provides a private vehicle with a driver and a dedicated guide to lead you through the city’s highlights. With pickup options from your hotel or downtown, the tour covers all the must-see sights, allowing you to learn about Chicago’s rich history and culture.
Based on the 5-star reviews, the tour delivers a comfortable and accommodating experience, making it a must-do for visitors and newcomers alike.
The host’s commitment to customer satisfaction ensures a seamless and enjoyable experience.
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Chicago Millennium Park Self-Guided Walking Tour
Visitors exploring Chicago’s renowned Millennium Park can embark on a captivating self-guided walking tour using a dedicated smartphone app.
This experience allows them to discover key attractions like the iconic Cloud Gate, also known as “The Bean,” the serene Lurie Garden, and the striking Crown Fountain at their own pace.
The hands-free audio stories, offline maps, and user-friendly interface make the tour accessible and easy to navigate, even for first-time visitors.
With a flexible duration and the ability to revisit favorite spots, this self-guided tour offers a personalized and crowd-free exploration of Millennium Park’s architectural and natural wonders.
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Chicago Riverwalk Self-Guided Walking Tour
Guests embarking on a self-guided walking tour of Chicago’s iconic Riverwalk can expect an immersive journey through the city’s captivating history and stunning architecture.
This engaging experience features captivating storytelling, a comprehensive route, and seamless offline functionality. The tour can be navigated via the Action’s Tour Guide App, which provides hands-free audio tales that activate based on location.
With flexible pacing and no cellular or Wi-Fi required, travelers can explore at their own pace, pausing anywhere along the way. Ideal for couples, the tour offers personalized stops and memorable keepsakes, ensuring a truly remarkable experience along the Riverwalk.
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Skip-the-Line The Field Museum of Natural History Exclusive Guided Tour
Bypassing the queues, travelers embark on an exclusive guided tour of the renowned Field Museum of Natural History in Chicago.
This 2.5-hour private tour, limited to 8 people, provides a comprehensive look at the museum’s vast collections. Guests skip the lines and enjoy an expert-led journey through the exhibits, delving into the museum’s rich history and scientific discoveries.
The tour is wheelchair accessible and near public transportation, making it convenient for visitors. With no large bags allowed and a moderate fitness level required, guests can focus on the captivating experience.
Reviews praise the guide’s exceptional knowledge, transforming the visit into a truly enlightening adventure.
Read our full review: Skip-the-Line The Field Museum of Natural History Exclusive Guided Tour Review
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Discovering Vintage Chicago: A Self-Guided Audio Tour of the Loop
Although the self-guided audio tour of Chicago’s Loop may lack the in-depth historical insights that some travelers desire, it nonetheless offers a convenient and accessible way for visitors to explore the city’s vintage charm at their own pace.
The tour, which can be accessed through the VoiceMap application, provides offline access to audio, maps, and geodata, allowing users to navigate the area at their convenience.
While the tour doesn’t include transportation, food, or tickets to museums, it’s wheelchair and stroller accessible, and service animals are allowed.
However, recent reviews suggest room for improvement in terms of detailed information and technical reliability.
Read our full review: Discovering Vintage Chicago: A Self-Guided Audio Tour of the Loop Review
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Vice, Crime and Gangsters in Chicago: A Self-Guided Audio Tour
Immersing oneself in Chicago’s notorious history of vice and crime, this self-guided audio tour transports visitors through the city’s storied gangster legacy.
Using a private smartphone app, explorers can download offline maps and audio to navigate iconic landmarks like the Wrigley Building and Riverwalk while delving into the city’s seedy underbelly.
With flexible scheduling and the ability to set their own pace, travelers can fully enjoy this captivating journey.
Although not wheelchair accessible, the tour caters to most visitors and provides a unique perspective on Chicago’s past.
While reviews are limited, this intimate experience promises an unforgettable glimpse into the city’s notorious history.
Read our full review: Vice, Crime and Gangsters in Chicago: A Self-Guided Audio Tour Review
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Chicagos Dark Side Smartphone (GPS/APP) Audio / Self Guided Walking Tour
Set out on a captivating journey through Chicago’s dark past with the “Chicago’s Dark Side Smartphone (GPS/APP) Audio / Self-Guided Walking Tour.”
This immersive experience allows visitors to explore the city’s notorious history of vice, crime, and hauntings at their own pace.
With a 4.7-star rating based on 3 reviews, this self-guided tour takes you along the Riverwalk and under bridges, sharing stories of ghostly encounters and the city’s infamous serial killers.
Priced at just $6.95 per person, it’s a convenient and affordable way to explore Chicago’s dark side, accessible daily from 12:00 AM to 11:30 PM.
No reservations needed – just confirm your booking and begin your chilling exploration.
Read our full review: Chicagos Dark Side Smartphone (GPS/APP) Audio / Self Guided Walking Tour Review
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Ultimate Chicago Self-Guided Walking Audio Tour Bundle
Visitors to Chicago can enjoy the Ultimate Chicago Self-Guided Walking Audio Tour Bundle, which provides a comprehensive and captivating exploration of the city’s landmarks and hidden gems.
This self-guided audio tour features engaging storytelling, offline maps, and GPS-enabled hands-free operation, allowing travelers to start, pause, and explore at their own pace.
The tour covers the Chicago Riverwalk and Millennium Park, ensuring a thorough experience.
With the ability to download the tour before arrival and share it with a companion, this flexible and convenient option is accessible to most travelers with compatible mobile devices.
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A Storied Neighborhood: a Self-Guided Audio Tour With Bill Ayers
The self-guided “A Storied Neighborhood” audio tour with Bill Ayers takes visitors on an engaging exploration of Chicago’s Hyde Park neighborhood.
Covering 3 miles over 1.5-2 hours, the tour provides a mix of local history, personal anecdotes, and insights into the community.
Accessible through the VoiceMap app, the tour can be experienced at one’s own pace.
While the walking distance may challenge some, the tour offers a well-rounded perspective on the University of Chicago and surrounding areas.
With a rating of 3.5 stars, the tour is a solid option for those seeking an immersive self-guided experience in Hyde Park.
Read our full review: A Storied Neighborhood: a Self-Guided Audio Tour With Bill Ayers Review
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Skip-the-Line Field Museum Natural History Semi-Private Guided Tour (8ppl Max)
For those seeking a comprehensive exploration of the Field Museum’s renowned natural history collection, the Chicago Field Museum of Natural History Semi-Private Guided Tour (8ppl Max) offers a skip-the-line, in-depth experience.
This 2.5-hour guided tour, limited to a maximum of 8 guests, provides access to the museum’s extensive exhibits, from dinosaur fossils to ancient artifacts.
The tour includes all entrance fees, while gratuities and transportation are optional.
Though not wheelchair accessible, the tour is stroller-friendly and suitable for those with a moderate fitness level.
Guests should note that increased security measures may cause delays, and collections may vary throughout the year.
Read our full review: Skip-the-Line Field Museum Natural History Semi-Private Guided Tour (8ppl Max) Review
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Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour
Transporting visitors back to the roaring 20s, the Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour invites explorers to enjoy the city’s musical heritage.
Available through the VoiceMap app, this affordable tour allows flexibility to start, pause, and restart at any time. With offline access to audio, maps, and geodata, the self-guided experience requires only a smartphone and headphones.
The tour covers Chicago’s Ragtime and Jazz eras, with a meeting point at 2 W Cermak Rd. While tickets to attractions aren’t included, the tour operates daily, making it an accessible way to discover the city’s musical roots.
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Art of a City, Downtown Chicago Semi-Private Guided Walking Tour
Embarking on a semi-private walking tour, explorers can enjoy the artistic treasures of Downtown Chicago.
Led by knowledgeable guides, the 2.5-hour excursion is capped at 12 guests, ensuring an intimate experience. Participants will marvel at the city’s architectural wonders and world-renowned museums, including the iconic Art Institute.
Priced from €50.29 per person, the tour is accessible via nearby public transportation, though strollers are welcome. With a moderate fitness level required, the experience provides a rundown of Chicago’s vibrant downtown.
Operated by Babylon Tours Chicago, the tour offers a lowest price guarantee and flexible booking options, allowing visitors to explore the city’s art and culture at their own pace.
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Art of a City, Downtown Chicago – Exclusive Guided Walking Tour
Visitors can enjoy the vibrant art and architecture of Downtown Chicago on this exclusive guided walking tour.
Over 2.5 hours, a professional guide will lead your private group through the city’s iconic landmarks, sharing insights into their design and history.
The tour is wheelchair and stroller accessible, with transportation options available. Priced from $51.94 per person, it offers a low-price guarantee and flexible booking.
Whether you’re a first-time visitor or a local looking to explore your city anew, this tour provides an in-depth, personalized experience of Downtown Chicago’s artistic marvels.
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Frequently Asked Questions
How Do I Get to the Starting Point for the Tour?
To get to the starting point of the tour, visitors can check the tour operator’s website or contact them directly for information on the meeting location and transportation options, such as public transit or driving directions with parking instructions.
Can I Bring My Own Food and Drinks on the Tour?
You can usually bring your own food and drinks on guided tours, but it’s best to check with the tour operator beforehand. Many tours don’t allow outside food and drink to avoid disruptions or messes during the experience.
What Is the Cancellation Policy if I Need to Reschedule?
Most guided tour companies offer flexible cancellation policies, typically allowing participants to reschedule or cancel their tour at no extra cost if done so within 24-48 hours of the scheduled tour. It’s best to review each company’s specific policy before booking.
Are There Any Discounts Available for Seniors or Students?
Many guided tour providers in Chicago offer discounts for seniors and students. Customers should check with the specific tour company to inquire about any available discounts and the requirements to qualify.
Can I Take Photos During the Tour?
Yes, you can typically take photos during guided tours in Chicago. Many tour companies encourage guests to capture the sights and experience. However, it’s best to check with the specific tour provider for any restrictions or policies regarding photography.
The Sum Up
Chicago offers a diverse array of guided tours, from Segway explorations and river cruises to exclusive museum visits and self-guided audio strolls. Whether you’re interested in architecture, art, history, or cocktails, there’s a tour that caters to your interests and allows you to discover the city’s hidden gems. With a range of options, visitors can tailor their Chicago experience to their preferences and make the most of their time in the city.