Chicago’s best tours deliver the city’s essentials without tourist traps or wasted time. The Chicago Architecture Foundation’s river cruise stands out as the city’s finest, with expert docents explaining 150 years of architectural innovation along the waterfront. Back on land, the 4-hour comprehensive city tour efficiently covers must-see spots like Millennium Park, Navy Pier, and historic neighborhoods. History buffs will appreciate the “Devil in the White City” tour, which brings the 1893 World’s Fair story to life through carefully researched locations.
I especially love the small-group food tours through neighborhoods like Wicker Park, where you’ll sample authentic Chicago specialties while learning about immigrant history. For families and those with mobility needs, the accessible hop-on-hop-off bus provides a practical overview with stops at major attractions.
Let’s explore our carefully selected top tours that showcase Chicago at its authentic best.
Key Points
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Chicago City Tour offers a highly recommended small-group experience with knowledgeable local guides, showcasing the city’s top landmarks and an optional architecture river cruise.
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Themed tours such as the “Devil In The White City” tour provide a unique exploration of Chicago’s dark history and haunted sites, with live English-speaking guides.
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Diverse exploration methods like the City Minibus Tour, Ultimate City Bike Tour, and Elevated Architecture Tour cater to various interests and preferences of travelers.
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Tours offer accessibility and customization, with private tours, wheelchair and stroller accessibility, and personalized experiences for families, couples, and first-time visitors.
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Chicago city tours provide competitive pricing with high satisfaction rates, flexible policies, and a range of options like the Foodie Tour and Architecture Tour to suit different budgets and interests.
Chicago City Tour With Architecture River Cruise Option
The Chicago City Tour with Architecture River Cruise Option provides a comprehensive introduction to the city’s iconic landmarks and architectural wonders.
Rated with a 95% traveler recommendation and a Badge of Excellence, this tour showcases Chicago’s top sights, including the Chicago River, Buckingham Fountain, and the Magnificent Mile.
Travelers praised the intimate small-group experience and the knowledgeable local guides, who offer engaging commentary and humor.
The optional river cruise provides an in-depth look at the city’s architectural history.
With convenient hotel pickup, free cancellation, and an affordable price, this tour is an excellent choice for first-time visitors or those seeking a well-rounded Chicago experience.
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Chicago: The Devil In The White City Bus Tour
Offering a chilling exploration of Chicago’s dark past, the Chicago: The Devil In The White City Bus Tour takes visitors on a 7-hour journey through the city’s haunting history.
Priced from $59 per person, the tour visits infamous sites like the Glessner House, the Marshall Field Jr. Mansion, and the Union Stockyards Gate, bringing to life the grim tales of serial killer H.H. Holmes and the 1893 Columbian Exposition.
With a live English-speaking guide, the tour promises an eerie yet captivating experience, including stops at the haunted Congress Plaza Hotel.
Visitors should prepare for graphic stories and an unsettling vibe as they explore Chicago’s grisly past.
Read our full review: Chicago: The Devil In The White City Bus Tour Review
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Chicago City Minibus Tour
One of the most popular city tours in Chicago, the Chicago City Minibus Tour provides a comprehensive 2-hour sightseeing experience for up to 10 guests.
Travelers enjoy comfortable transport in a 12-passenger, air-conditioned minibus, with four photo stops at major landmarks like Museum Campus, Buckingham Fountain, Magnificent Mile, and Millennium Park.
The tour features live narration about Chicago’s history and culture, and is recommended by 99% of previous participants.
While not wheelchair accessible, the tour is suitable for all weather conditions.
Priced at $47.95 per person with free cancellation, it offers an excellent introduction to the city, especially for first-time visitors.
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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 hidden gems.
For $132 per person, travelers can reserve the tour and pay later, with a free cancellation policy up to 24 hours in advance.
The tour includes round-trip transportation, a driver and guide, and visits to key sights like Millennium Park, Grant Park, Michigan Avenue, and Navy Pier.
Customizable options allow guests to add attractions like the Art Institute of Chicago, 360 Chicago, and a Chicago River Boat Architecture Cruise.
With a duration of 1 day and a starting point at Millennium Park, this tour provides a well-rounded introduction to the Windy City.
Read our full review: Chicago: Full-Day Guided City Tour by Bus Review
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Chicago Private Custom City Tour With Hotel Pick up
Travelers seeking a personalized exploration of Chicago’s iconic landmarks and hidden gems can embark on the Chicago Private Custom City Tour with Hotel Pick up.
This highly-rated tour offers a custom experience, allowing guests to choose their own destinations and stops. With a knowledgeable guide providing in-depth commentary on the city’s history, architecture, and culture, visitors can discover notable sights like Millennium Park, Wrigley Field, and the largest Starbucks in the world.
Comfortable transportation in a spacious Landrover ensures a smooth journey through Chicago’s traffic. Praised for its engaging guides and tailored approach, this tour is an excellent choice for first-time visitors and families seeking a memorable adventure in the Windy City.
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Chicago: City Minibus Tour With Optional Architecture Cruise
Visitors to Chicago can embark on a comprehensive city minibus tour that showcases the iconic landmarks and vibrant neighborhoods of the Windy City.
The 2-4.5 hour tour is priced from €45.63 per person and provides a small-group experience with a live guide offering expert commentary.
Highlights include views of the Chicago River, photo stops at the skyline and Buckingham Fountain, and explorations of The Loop and Gold Coast areas.
For an added experience, travelers can opt for a 75-minute architectural cruise on the river, learning about the city’s renowned buildings and engineering feats.
With high ratings for knowledgeable guides and memorable experiences, this tour is a must-do for visitors.
Read our full review: Chicago: City Minibus Tour With Optional Architecture Cruise Review
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Chicagos Ultimate City Bike Tour
For those seeking a unique way to explore the Windy City, Chicago’s Ultimate City Bike Tour offers an engaging and informative experience.
With a 99% recommendation rate and a Badge of Excellence, this 9-mile tour showcases the city’s highlights at a comfortable pace. Guests will enjoy the scenic ride along Lake Michigan, the Riverwalk, and Navy Pier, while professional guides provide quality information and interaction.
Suitable for most ages and fitness levels, the tour includes a bicycle, helmet, and knowledgeable staff. Reviewers praise the expertise and friendliness of the guides, as well as the safety and enjoyable pace of the experience.
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Love Is in the Windy City – Chicago Walking Tour
On a romantic stroll through the heart of Chicago, the “Love Is in the Windy City – Chicago Walking Tour” invites couples to enjoy the city’s captivating landmarks and vibrant atmosphere.
Priced at Kč 14,418 for a private group of up to 4 participants, the 2-hour guided tour showcases the iconic Millennium Park, the reflective Cloud Gate (The Bean), and the picturesque Navy Pier.
Along the way, a local guide provides insightful commentary on the city’s history and architecture, while allowing ample time for couples to capture memorable photographs.
With free cancellation and a “reserve now, pay later” option, this tour offers a delightful and convenient way to explore Chicago’s romantic side.
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Best of Chicago: Architecture & Highlights City Private Tour
The “Best of Chicago: Architecture & Highlights City Private Tour” invites small groups to embark on an immersive exploration of the city’s architectural and historical wonders.
Capped at 12 participants, the private walking tour showcases iconic landmarks like the Picasso Statue, Chicago Riverwalk, and Millennium Park.
Along the way, the knowledgeable local guide shares insights, while participants savor popcorn and chocolate tastings.
With a convenient meeting point and optional pickup, the 3-hour tour offers wheelchair and stroller accessibility, making it suitable for families.
Reviewers praise the guides’ enthusiasm and ability to personalize the experience, highlighting the tour’s value for those interested in Chicago’s rich history and architecture.
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Chicago: Ghosts & Hauntings of the Windy City Walking Tour
Chicago’s rich history extends beyond its iconic architecture, delving into the supernatural realm.
The “Chicago: Ghosts & Hauntings of the Windy City Walking Tour” allows visitors to explore the city’s haunted past. For $32, you’ll embark on a 1-hour walking tour led by experienced guides who share chilling stories of mobsters, serial killers, and ghostly encounters.
The tour visits locations like Lincoln Park, Oz Park, and the Red Lion Pub, where you might encounter a Victorian woman in white or other paranormal phenomena.
Suitable for all ages, this tour provides an engaging and informative experience for those interested in Chicago’s spookier side.
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Chicago City Tour: Elevated Architecture Tour With Train Ticket Included
For those seeking a unique perspective on Chicago’s renowned architecture, the “Chicago City Tour: Elevated Architecture Tour with Train Ticket Included” offers an immersive experience.
This two-hour tour highlights the city’s diverse architectural styles, from Brutalist to Beaux Arts, with a professional guide providing in-depth knowledge and engaging narratives.
Travelers will enjoy a 15-minute train ride on the Chicago Elevated Rail system, offering a birds-eye view of the city.
With a maximum group size of 10, this tour promises an intimate and personalized exploration of Chicago’s architectural heritage.
Though not wheelchair accessible, the tour allows service animals and is suitable for those comfortable with stairs and standing.
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Chicago: Ultimate City Attractions Bike Tour
This 3-hour Chicago: Ultimate City Attractions Bike Tour allows visitors to marvel at the city’s iconic skyline and picturesque lakefront.
Led by knowledgeable guides, the tour takes cyclists to Millennium Park’s renowned sculptures, Northerly Island’s serene nature area, and the striking architecture of the Museum Campus.
Participants will also witness the majestic Buckingham Fountain.
Suitable for first-time visitors, the kid-friendly tour provides bike rentals, helmets, and a live English-speaking guide.
With an overall rating of 4.8/5 from 29 reviews, this bike tour offers an engaging and informative way to explore Chicago’s top attractions at a reasonable price.
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Chicago Private Foodie Tour: Windy City Faves
Exploring Chicago’s iconic culinary scene, the Chicago Private Foodie Tour: Windy City Faves takes visitors on a delightful journey through the city’s most beloved local specialties.
This private tour focuses on must-try dishes like deep-dish pizza, hot dogs, Italian beef sandwiches, and donuts.
Along the way, guests will experience top landmarks like the Wrigley Building, Millennium Park, and Magnificent Mile.
The tour emphasizes personal, flexible travel, with an English-speaking guide providing insights on Chicago’s culture and history between food stops.
Priced from $288 per person with free cancellation, this highly-rated tour offers a satisfying taste of the Windy City’s famous flavors.
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The Sum Up
Chicago offers a diverse range of city tours catering to various interests. From architectural river cruises and haunted walking tours to private foodie experiences, there’s something for all. Whether you’re a first-time visitor or a seasoned local, these tours provide an engaging and insightful way to explore the city’s rich history, iconic landmarks, and vibrant neighborhoods.