Chicago’s city tours fall into four main categories, all worthwhile depending on your interests. Walking tours pack in the most detail with knowledgeable guides explaining the city’s famous architecture and history. The Chicago Architecture Foundation’s river cruise is a must-do – you’ll get outstanding views of downtown skyscrapers while learning fascinating stories about their design. For families and first-timers, the hop-on-hop-off bus tours efficiently cover major attractions with minimal walking. Ghost tours through historic neighborhoods like Gold Coast and Lincoln Park offer spooky evening entertainment with substance. Let’s look at our top-rated tour choices for experiencing the Windy City.
Key Points
- For a comprehensive private city tour, consider the “Chicago 6-Hour City Tour by Sedan” which covers up to 70 miles and includes a knowledgeable driver/guide.
- The “Chicago City Tour with Architecture River Cruise” provides a well-rounded experience, combining a bus tour and an architectural river cruise for panoramic views of the city.
- The “Chicago City Tour: Elevated Architecture Tour” offers a personalized exploration of the city’s iconic skyline, highlighting various architectural styles in a two-hour tour.
- The “Ghosts & Hauntings Walking Tour” in Lincoln Park provides a one-hour guided experience focused on the area’s haunted locations and history.
- The “Ultimate City Attractions Bike Tours” offer a 3-hour active exploration of Chicago’s landmarks, covering 9 miles and accommodating most ages.
Chicago Private Custom City Tour With Hotel Pick up
Why not start your Chicago sightseeing experience with a private custom city tour that offers hotel pick-up?
This efficient tour covers the city’s highlights, including the Lincoln Park Conservatory, Millennium Park, and Museum Campus. With a duration of several hours, you’ll get to explore the city at a comfortable pace.
Boasting a 5.0 rating from 189 reviews, 98% of travelers recommend this personalized experience. At $539 per group (up to 5 people), it’s a great value, and you can even cancel up to 24 hours beforehand for free.
Whether you’re a first-time visitor or seeking a deeper understanding of Chicago, this private tour is an excellent choice.
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Chicago: Full-Day Guided City Tour by Bus
This full-day guided city tour by bus offers visitors a comprehensive exploration of Chicago’s iconic landmarks and attractions. Priced at €125.59 per person, the tour includes round-trip transportation, a driver and guide, and highlights such as the Cloud Gate, Grant Park, and the Art Institute of Chicago.
Customization options allow visitors to upgrade their experience with entry tickets to popular attractions like the 360 Chicago and the Chicago Architectural Cruise.
With a flexible cancellation policy and the option to reserve now and pay later, this tour provides an efficient and hassle-free way to discover the best of Chicago in a single day.
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Chicago City Tour With Architecture River Cruise Option
For those seeking an efficient and comprehensive way to explore Chicago’s iconic landmarks and architectural marvels, the Chicago City Tour with Architecture River Cruise Option is a top-rated choice.
Rated 4.8 out of 645 reviews, this combination bus and boat tour offers a well-paced itinerary led by knowledgeable guides. Passengers can expect to visit renowned attractions like the Museum Campus, Buckingham Fountain, and the Rookery Building, while also enjoying panoramic views of Lake Michigan and passing by landmarks like the Willis Tower and Millennium Park.
The optional river cruise provides an in-depth look at the city’s renowned architecture. With complimentary hotel pickups and a personalized experience, this tour is an efficient and enjoyable way to experience the best of Chicago.
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Chicago: Ghosts & Hauntings of the Windy City Walking Tour
Explore Chicago’s haunted past on the Ghosts & Hauntings of the Windy City Walking Tour.
This 1-hour walking tour takes visitors through Lincoln Park, where they’ll discover ghostly tales of gangsters and serial killers. The tour visits several haunted locations, including Oz Park, Golden Dagger, and the Red Lion Pub.
Participants may even encounter the Victorian woman in white at Lincoln Park Zoo. Guided by a seasoned expert, the tour covers a mile of Chicago’s most haunted real estate.
Priced at $32 per person, the tour offers free cancellation up to 24 hours in advance and accepts reservations with payment later.
With an overall rating of 4.4/5, this tour is a great choice for couples, groups, solo travelers, and families.
Read our full review: Chicago: Ghosts & Hauntings of the Windy City Walking Tour Review
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Chicago City Minibus Tour
The Chicago City Minibus Tour offers visitors a comprehensive introduction to the Windy City’s iconic landmarks and hidden gems. Rated 4.9 out of 5 with 308 reviews, this small-group tour takes guests on a 2-hour journey through the city’s key sights, including the Museum Campus, Buckingham Fountain, and Millennium Park.
With live narration from knowledgeable guides, travelers learn about Chicago’s rich history and culture. The tour’s four photo stops allow for memorable snapshots, and hotel pickup is available for added convenience.
Wheelchair-accessible but not suitable for infants, the minibus experience operates year-round, rain or shine, ensuring a smooth and enjoyable adventure for first-time visitors and seasoned Chicago explorers alike.
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Chicago: Ultimate City Attractions Bike Tour
Embark on an exhilarating 3-hour bike tour that showcases Chicago’s most iconic city attractions. Priced at $54.99 per person, the “Chicago: Ultimate City Attractions Bike Tour” takes you on a family-friendly journey along cycle paths, exploring the city’s skyline, lakefront, and renowned museums.
Hop on a provided bike and helmet, and let the live tour guide lead you through Millennium Park, Northerly Island, and Buckingham Fountain, while sharing engaging commentary on Chicago’s history and unique artifacts.
With a 4.8/5 rating based on 29 reviews, this tour is a must-try for first-time visitors seeking an active and informative way to experience the Windy City.
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Chicagos Ultimate City Bike Tour
For those seeking an engaging and informative way to experience the best of Chicago, the Chicago’s Ultimate City Bike Tour offers an exhilarating 3-hour adventure.
Covering 9 miles and iconic sites like the Museum Campus and Buckingham Fountain, this highly-rated tour provides a unique perspective of the city.
Operated by professional guides, the tour accommodates up to 15 travelers and is suitable for most ages and fitness levels.
Bicycles and helmets are included, and the primarily bike-path route is ideal for families.
With a 99% traveler recommendation and 5-star reviews, this tour is a must for anyone looking to explore Chicago at a relaxed pace while enjoying stunning views.
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Chicago: City Minibus Tour With Optional Architecture Cruise
Explore Chicago’s iconic landmarks on a comprehensive minibus tour with the option to add an architectural cruise along the Chicago River.
The tour covers downtown Chicago and nearby neighborhoods, highlighting the Chicago River, Buckingham Fountain, Museum Campus, Millennium Park, and Gold Coast.
Enjoy three photo stops, including the stunning city skyline. For a deeper dive into the city’s architecture, add the 75-minute outdoor cruise that provides insights into notable landmarks like the John Hancock building.
With a live English-speaking guide, small group size, and hotel pickup, this tour offers an efficient and informative way to experience the best of Chicago.
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Best of Chicago: Architecture & Highlights City Private Tour
This private tour offers an immersive experience that showcases Chicago’s iconic architecture and highlights. Priced from $245 per group of up to 12 people, the 3-hour walking tour earns a stellar 4.9/5 rating from 95 reviews, with 98% of travelers recommending it.
Guests start at the historic Chicago Theatre and explore the city’s hidden gems, learning about the architectural history from a knowledgeable, English-speaking guide. Along the way, they enjoy snacks like popcorn and chocolate tastings.
The tour culminates at Millennium Park, though an optional 2-hour food walking tour is available. Catering to first-time visitors, this experience is accessible for most travelers, including those with mobility aids.
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Love Is in the Windy City – Chicago Walking Tour
Chicago’s “Love Is in the Windy City” walking tour offers an intimate exploration of the city’s beloved landmarks.
The 2-hour tour, priced at $602.26 for up to 4 participants, provides a rundown of Millennium Park, Crown Fountain, Cloud Gate (The Bean), DuSable Bridge, and Navy Pier.
Guests can expect a guided tour of these iconic attractions, learning about their history and architecture from a local expert.
The tour’s flexible booking and free cancellation policy make it an attractive option for visitors seeking a personalized Chicago experience.
Whether you’re a first-time traveler or a seasoned local, this walking tour promises a memorable outing filled with art, culture, and stunning views.
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The Devil in the White City: A Haunting History Tour
Delving into the dark history of 19th-century Chicago, the “The Devil in the White City: A Haunting History Tour” offers visitors a chilling exploration of the city’s past.
Operated by Chicago Hauntings, the half-day tour takes guests through key sites connected to the 1893 World’s Fair and the notorious serial killer H.H. Holmes.
With a badge of excellence and 4.5 stars, the tour provides insightful commentary from knowledgeable guides as participants travel by bus and take guided walks.
While some travelers found the tour leaned more toward history than haunting elements, the tour’s highlights, including the “Murder Castle,” promise an engrossing look at Chicago’s haunting legacy.
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Chicago City Tour: Elevated Architecture Tour With Train Ticket Included
Offering a captivating exploration of Chicago’s renowned elevated architecture, the “Chicago City Tour: Elevated Architecture Tour with Train Ticket Included” provides visitors with a unique perspective on the city’s iconic skyline.
Rated 4.7 out of 54 reviews, this two-hour tour takes travelers on a journey through the city’s architectural highlights, including Brutalist, Mid-Century Modern, Beaux Arts, and Post Modernist styles.
With a maximum group size of 10, the tour offers a personalized experience led by professional and certified guides.
While not wheelchair accessible, the tour includes a fare for the Chicago Elevated Rail system, allowing participants to enjoy the city’s renowned transportation network.
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Windy City Ghosts: Hauntings of Chicago Walking Tour
Intrigue swirls through the streets of Chicago as the Windy City Ghosts: Hauntings of Chicago Walking Tour guides visitors on a spine-tingling exploration of the city’s paranormal past.
This 4.4-star rated tour delves into intensely researched true stories of history and documented accounts of hauntings. Professional and courteous guides bring the eerie tales to life while leading guests to the Tin Man Statue in Oz Park, the meeting point.
Though some reviewers desired more in-depth exploration of haunted venues, the tour’s highlights include learning about Chicago’s ghostly lore and engaging paranormal experiences.
At $25 per person, this 15-person maximum walking tour offers an atmospheric look into the Windy City’s supernatural side.
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Chicago 6-Hour City Tour by Sedan
The Chicago 6-Hour City Tour by Sedan provides a comprehensive exploration of the Windy City’s iconic landmarks and hidden gems.
Operated by Chief Chicago Limo, this private tour allows visitors to discover the city’s rich history and vibrant culture at their own pace.
With a duration of 6 hours and a maximum of 2 participants, the tour covers up to 70 miles within the city, ensuring a well-rounded experience.
Pickup options, parking, and a knowledgeable driver/guide are all included, making this an efficient and convenient way to see the best of Chicago.
Positive reviews highlight the tour’s ability to provide an enriching experience in a limited time, as well as the excellent service and luxury vehicle.
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4-Hour Chicago City Tour by SUV
For time-pressed visitors to Chicago, the 4-Hour Chicago City Tour by SUV provides an efficient and personalized way to explore the city’s top landmarks.
This private tour offers the flexibility to visit iconic sites like Navy Pier, Wrigley Field, Michigan Avenue, and Millennium Park at your own pace. With a private driver and up to 50 miles included, you can make the most of your time in the city.
The tour’s logistics are straightforward, with pickup and drop-off at a downtown location. And with free cancellation and a pay-later option, booking this tour is hassle-free.
Given the positive customer feedback, this tour seems like an excellent choice for a comprehensive Chicago experience.
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Private Tour in Spanish of the City of Chicago
Visitors seeking an immersive Spanish-language tour of Chicago can consider the Private Tour in Spanish of the City of Chicago. Rated 2.3 out of 5 based on 3 reviews, the tour lasts for a confirmed duration and operates daily from 9 AM to 5 PM between August 20, 2022, and October 13, 2025.
Pickup is available from Union Station, hotels, or airports. The tour includes a drink and Chicago souvenir but isn’t wheelchair accessible.
While past customers praised the guide’s professionalism, others reported issues with tour execution and communication. Interested travelers should confirm details with the local provider in advance.
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Chicago, Cloud Gate, Grant Park Full-Day City Tour
Although the Private Tour in Spanish may not have met all guests’ expectations, the Chicago, Cloud Gate, Grant Park Full-Day City Tour offers a comprehensive exploration of the Windy City.
Priced at $113.90 per person, the tour includes professional transportation, a knowledgeable guide, and admissions to top attractions like the Art Institute of Chicago and 360 Chicago.
With a maximum of 55 travelers, the tour provides a personalized experience. Participants should note the meeting point, departure time, and tour guide’s ability to adjust the itinerary as needed.
Children under 18 must be accompanied by an adult, and those under 8 require a booster seat.
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Private Custom City Tour in Chicago
Travelers seeking a more personalized exploration of Chicago can consider the Private Custom City Tour. Starting from $1,280 per person, this tour offers a tailored experience with a professional guide.
Pickup and drop-off at any location in the Chicagoland area are included, and the tour is wheelchair and stroller accessible. While gratuities aren’t included, the tour allows for free cancellation up to 24 hours in advance.
With an overall rating of 4.5/5 based on 3 reviews, this tour provides a private and customized way to discover the Windy City. The notable review highlights the guide’s expertise, though COVID-related restrictions impacted the full experience.
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Chicago City Private Walking Tour
A captivating Chicago city walking tour offers visitors an immersive exploration of the Windy City’s iconic landmarks.
This private 3-hour walking tour showcases the city’s most famous sights, including The Bean, Union Station, Wrigley Building, and the Magnificent Mile.
Led by a local English-speaking guide, the tour provides an insider’s perspective and includes a CTA train pass for convenient transportation.
Along the way, guests can enjoy a local snack.
Accessible to wheelchair users and stroller-friendly, the tour accommodates most travelers.
Bookings for parties under 4 can be made by phone, and groups will have a private experience.
With 5-star reviews, this comprehensive walking tour is an excellent way to discover the heart of Chicago.
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10 Hours Private City Tour in Chicago – Chartered Tour
This expansive 10-hour private city tour in Chicago provides an unparalleled opportunity to explore the Windy City’s most iconic landmarks and hidden gems.
With a professional driver, air-conditioned transportation, and all fees and taxes covered, this private tour offers a personalized and comprehensive experience.
Passengers can request infant seats, though the tour isn’t wheelchair accessible. Standard luggage is permitted, with extra fees for oversized items.
Booking is flexible, with free cancellation up to 24 hours in advance and a reserve now, pay later option.
Whether you’re a first-time visitor or a Chicago local, this private tour is an excellent way to discover the city’s diverse attractions and rich history.
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Recap
Chicago offers a diverse range of city tours, from private custom tours to full-day bus tours and walking tours focused on the city’s architecture, history, and haunted sites. Visitors can choose from a variety of options to best suit their interests and preferences, making the most of their time in the Windy City.