The smartest way to explore Chicago is through its excellent city tours. Small-group minibus tours are perfect for seeing the main downtown sights without wearing out your feet, while bike tours – especially in summer – offer a breezy, fun alternative. I particularly love the history-themed walking tours, where passionate guides share stories of Chicago’s fascinating past, from gangsters to great fires. Food tours through neighborhoods like West Loop and Wicker Park are another favorite, letting you taste the city’s famous deep-dish pizza, hot dogs, and ethnic specialties. For flexibility, private custom tours work great for families or special interests. Let’s explore the best Chicago tours worth your time and money.
Good To Know
Chicago offers a variety of highly-rated city tours, including small-group minibus tours, unique themed tours, and private/custom tours for personalized experiences.
Tour options cater to diverse interests, such as architecture, history, food, and romance, ensuring a comprehensive and engaging exploration of the city.
Tours are led by knowledgeable local guides who provide valuable insights, enhancing the overall experience for visitors.
Accessibility features, including accommodations for wheelchairs and strollers, ensure inclusivity and make the tours accessible to a wide range of travelers.
High ratings, positive feedback, and flexible cancellation policies contribute to the overall quality and reliability of the city tour offerings in Chicago.
Chicago Small-Group City Tour With Optional Architecture River Cruise
The Chicago Small-Group City Tour with Optional Architecture River Cruise offers travelers a comprehensive way to explore the iconic landmarks and architectural gems of the Windy City.
Rated 4.8 out of 645 reviews and recommended by 95% of travelers, this tour provides a personalized experience in a comfortable, large-windowed minibus. Guests can choose to upgrade their tour with an open-top boat cruise focusing on Chicago’s renowned architecture.
Along the way, an expert guide leads the small group of 10 or fewer passengers through Downtown Chicago, with photo stops at must-see locations like the Museum Campus, Buckingham Fountain, and the Rookery Building.
The tour includes hotel pickup and drop-off, ensuring a seamless and enjoyable experience.
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Chicago City Minibus Tour
Exploring Chicago’s iconic landmarks and architectural marvels has never been easier than with the Chicago City Minibus Tour.
This 2-hour small-group tour ferries travelers around the Windy City in a comfortable 12-passenger minibus, making four photo stops at must-see spots like the Museum Campus, Buckingham Fountain, and Millennium Park.
With a knowledgeable guide providing live narration on Chicago’s history and culture, passengers can sit back and soak in the sights.
Boasting a stellar 99% recommendation rate from previous travelers, the tour is an excellent choice for first-time visitors and those seeking an engaging overview of the city.
At just $47.95 per person, it’s a budget-friendly way to experience the best of Chicago.
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Chicagos Ultimate City Bike Tour
Enjoy Chicago’s iconic landmarks and scenic waterfront on the thrilling Chicago’s Ultimate City Bike Tour. Rated 4.9 out of 5 stars with 169 reviews, this top-rated tour allows you to explore the Windy City’s must-see sites at a leisurely pace.
Cycle through Museum Campus, Circle Buckingham Fountain, and discover public art, parks, and museums. The relaxed route is suitable for all ages and fitness levels, with a maximum of 15 travelers per tour.
Bike, helmet, and a knowledgeable guide are included, and the tour ends back at the meeting point. With consistently positive reviews, this tour is a fantastic way to experience the best of Chicago on two wheels.
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The Devil in the White City: A Haunting History Tour
Although the name may suggest a thrilling haunted tour, “The Devil in the White City: A Haunting History Tour” primarily delves into the captivating history and legends surrounding the 1893 Chicago World’s Fair and the notorious serial killer H.H. Holmes.
Led by knowledgeable guides, the half-day tour explores key locations like the Prairie Avenue Historic District and the infamous “Murder Castle.”
While the tour offers a mix of history and ghost stories, some travelers feel it leans more towards the historical aspects.
Considering the walking involved, the tour may not be suitable for those with mobility limitations, and it may not fully satisfy expectations for a dedicated haunted experience.
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Chicago City Tour by L Train
Visitors can embark on a captivating Chicago City Tour by L Train, which offers a unique opportunity to explore the city’s iconic landmarks and learn about its rich history.
Rated 4.9 out of 5 stars with 96% of travelers recommending it, this tour provides an all-day CTA pass, a small treat, and a knowledgeable local guide.
Participants can expect a small group size of up to 12 travelers, ensuring personalized attention.
The tour includes stops at the Chicago Theatre, the Loop, and the Chicago Riverwalk, among other landmarks.
With free cancellation up to 24 hours in advance, this tour is an excellent choice for those seeking an immersive and informative Chicago experience.
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6 Hours of Chicago City Tour Sedan
The Chicago City Tour Sedan offers visitors a comprehensive way to explore the city’s iconic landmarks and attractions.
This private 6-hour driving tour is ideal for first-time visitors or those with limited time, covering major sights like Navy Pier, Michigan Avenue, Wrigley Field, and Millennium Park.
Travelers will ride in a luxury, updated sedan with a dedicated driver who provides local insights throughout the tour.
The package includes up to 70 miles of travel, with additional costs for exceeding the limit.
Priced from $960.00 per group (up to 2 people), the tour features a flexible schedule, free cancellation, and a lowest price guarantee, making it a convenient and affordable option for discovering Chicago.
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Private Custom City Tour in Chicago
A private custom city tour in Chicago offers travelers a personalized and flexible way to explore the city’s iconic landmarks and hidden gems.
With a 4.5/5 rating based on 3 reviews, this tour is fully customizable to visitors’ interests, whether they’re interested in architecture, history, art, museums, food, or neighborhoods.
Travelers will enjoy the comfort of a private vehicle and the expertise of a professional guide, with hotel pickup and drop-off included.
The tour is wheelchair and stroller accessible, and with a no-touch check-in policy, it’s ideal for first-time or time-pressed visitors.
Priced from $880 per person, it offers a lowest price guarantee and a reserve now, pay later option.
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Chicago Full-Day City Tour
On this full-day tour, guests discover the best of Chicago’s iconic landmarks and sights. The tour departs at 8 AM from Millennium Park, exploring attractions like Grant Park, Michigan Avenue, and more.
Customizable options include the Art Institute of Chicago, the 360 Chicago observation deck, and the Chicago Architectural Cruise. Professional transportation, a driver and guide, and food and beverage are included.
Children under 18 must be accompanied by an adult, and guests with disabilities should provide advance notice for accommodations.
Free cancellation is available up to 24 hours before the tour, though attraction tickets must be purchased through the tour company.
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Private Tour in Spanish of the City of Chicago
For those seeking a more intimate and personalized exploration of Chicago, the Private Tour in Spanish of the City of Chicago offers a unique opportunity.
Covering the city’s highlights, this 3-hour private tour includes a drink and souvenir. Starting at the Union Station Transit Center, the tour is led by a knowledgeable Spanish-speaking guide and can be customized to match guests’ interests.
While the tour isn’t wheelchair accessible, it’s stroller-friendly. Customers should provide their pickup location, typically a hotel or airport, and confirm the time in advance.
With a rating of 2.3 out of 5 stars based on 3 reviews, the tour has received both positive and negative feedback from past participants.
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Art of a City, Downtown Chicago Semi-Private Guided Walking Tour
Enjoy the rich artistic heritage of downtown Chicago on the Art of a City, Downtown Chicago Semi-Private Guided Walking Tour.
This 2.5-hour walking tour, limited to a maximum of 12 guests, takes you through the city’s iconic landmarks and hidden gems. You’ll skip the lines and enjoy exclusive access, led by a knowledgeable guide.
Highlights include the Art Institute of Chicago, the iconic Lions statues, and other significant architectural and cultural sites.
With a moderate fitness level required, this tour is perfect for those seeking an in-depth exploration of Chicago’s vibrant art scene.
Conveniently located near public transportation, this tour is a must-do for art enthusiasts visiting the Windy City.
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Private 3 Hour Walking Tour in Chicago City
Set out on a captivating 3-hour private walking tour of Chicago’s iconic landmarks with a knowledgeable local guide.
Explore the city’s architectural marvels, including the renowned Bean, Union Station, and the Wrigley Building, while enjoying the vibrant atmosphere of the Magnificent Mile.
Enjoy a local snack and an all-day CTA train pass as part of the inclusive package.
With wheelchair and stroller accessibility, as well as service animal accommodations, this tour caters to a wide range of travelers.
Rated 5 stars by all previous participants, this private tour promises an unforgettable experience in the heart of Chicago.
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Love Is in the Windy City – Chicago Walking Tour
Discover the romantic side of Chicago on this private walking tour that showcases the city’s iconic landmarks and hidden gems. Priced from $308.86 per person, the “Love is in the Windy City” tour takes you on a 3-hour journey through the heart of Chicago, starting at Millennium Park and ending at the picturesque Navy Pier.
Led by a local professional guide, you’ll explore the city’s most romantic spots, from scenic vistas to cozy cafes. While the tour isn’t wheelchair accessible, it’s suitable for most travelers.
Keep in mind, this is a non-refundable tour, so be sure to confirm your availability before booking.
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Art of a City, Downtown Chicago – Exclusive Guided Walking Tour
The “Art of a City, Downtown Chicago – Exclusive Guided Walking Tour” takes you on a captivating journey through the heart of Chicago’s vibrant downtown.
This 2.5-hour private walking tour offers an immersive experience, led by a professional guide. Explore the city’s iconic landmarks, from the Art Institute to the bustling streets, while learning about Chicago’s rich history and architecture.
The tour is wheelchair-friendly and accessible for strollers, making it suitable for visitors of all abilities. Priced at €49.98 per person, the tour includes all fees and taxes, ensuring a hassle-free experience.
With free cancellation up to 24 hours in advance, this tour provides flexibility and convenience for your Chicago adventure.
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Food Walking Tour in Windy City of Chicago
Traversing the vibrant culinary landscape of Chicago’s neighborhoods, this Food Walking Tour immerses participants in the diverse flavors that have shaped the Windy City’s gastronomic identity.
This 3-hour excursion starts at 11 am, meeting at the iconic Portillo’s and Barnelli’s location. With a maximum of 12 travelers, the tour offers an intimate experience guided by local experts who share well-researched insights into the city’s rich food history.
Guests can expect a variety of delectable tastings, wheelchair and stroller accessibility, and easy access to public transportation. Priced at $88 per person, the tour provides an exceptional value with inclusions such as food, a local guide, and gratuity, along with a flexible 24-hour cancellation policy.
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The Sum Up
Chicago offers a diverse array of city tours catering to various interests. From guided walking tours exploring the city’s architecture, haunted history, and culinary delights, to bike and minibus tours providing a rundown, there’s something to suit every traveler’s preferences. Whether you’re seeking an in-depth cultural experience or a leisurely sightseeing adventure, Chicago’s city tours provide an engaging and informative way to discover the Windy City’s vibrant charm.