Private tours in Chicago cut through the tourist chaos and deliver authentic experiences that matter. Skip-the-line access at major landmarks and hotel pickup make these tours practical and time-efficient. The city’s architectural walking tours stand out – guides know their stuff and provide clear historical context. Food tours through neighborhoods like West Loop and Wicker Park offer real local flavors, not tourist traps.
For the best views, book a helicopter tour at sunset – it’s worth the splurge to see the skyline light up. Architecture river cruises with private guides give you breathing room to ask questions and snap photos without fighting crowds.
Our favorite picks focus on value, local expertise, and authentic Chicago experiences.
Browse our top recommended private tours below:
Key Points
- Private custom city tours offer flexibility, convenience, and access to iconic Chicago landmarks like Millennium Park and Museum Campus.
- Guided walking tours provide in-depth exploration of the city’s architectural heritage and local food scene.
- Customizable boat tours on the Chicago River allow visitors to learn about the city’s diverse architectural styles.
- Specialized art and helicopter tours offer unique perspectives on Chicago’s skyline and top attractions.
- Private architecture and movie site tours cater to enthusiasts seeking more in-depth experiences of the city’s iconic buildings and filming locations.
Chicago Private Custom City Tour With Hotel Pick up
One of the standout private tours in Chicago is the “Chicago Private Custom City Tour With Hotel Pick up”. Rated 4.9 based on 189 reviews, this tour offers a personalized sightseeing experience with hotel pick-up.
Highlights include stops at iconic landmarks like Lincoln Park Conservatory, Millennium Park, and Museum Campus, where travelers can learn about the city’s rich history.
The flexible duration allows for customizing the itinerary, and the tour is accessible for infants and wheelchair users.
With a competitive price and a lowest price guarantee, this tour is an ideal option for first-time visitors looking to maximize their limited time in the Windy City.
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Chicago : Loop Private Walking Tour With a Guide
Enjoy the captivating architecture of Chicago’s Loop on this private walking tour.
Explore the city’s pivotal role in the global Art Deco movement, marveling at the intricate facades and lavish designs from the Jazz Age.
Your knowledgeable local guide will provide insights into Chicago’s architectural legacy, tailoring the experience to your individual interests.
With a duration of 2 hours and a price from $116.11 per person, this tour offers a flexible and customizable way to discover both the main tourist sights and lesser-known areas.
Wheelchair accessible and with a free cancellation policy, this tour is an excellent choice for an in-depth exploration of Chicago’s architectural wonders.
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Best of Chicago: Architecture & Highlights City Private Tour
For travelers seeking a comprehensive exploration of Chicago’s renowned architecture and top sights, the “Best of Chicago: Architecture & Highlights City Private Tour” offers an immersive experience.
This 3-hour small-group walking tour takes participants through Downtown Chicago, showcasing iconic landmarks like the Picasso Statue, Chicago Riverwalk, and Millennium Park.
Led by knowledgeable guides, the tour delves into the city’s rich history and architectural marvels.
Highlights include local food tastings, a transit pass, and accessibility for wheelchair users and families.
With a 5.0 overall rating from 95 reviews, this tour is a must-do for those wanting to discover Chicago’s hidden gems and captivating stories.
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Chicago in a Day: Food and Architecture Private Walking Tour
Travelers exploring Chicago’s vibrant culture can embark on the “Chicago in a Day: Food and Architecture Private Walking Tour“, a comprehensive 5-hour experience showcasing the city’s renowned architecture and diverse culinary delights.
Priced from $272.50 per person, this private tour provides an in-depth look at the city’s iconic landmarks, including the Chicago Riverwalk and Millennium Park, while also treating guests to a sampling of heritage cuisine in the Chicago Loop.
Led by a local English-speaking guide, the tour immerses visitors in the history and stories behind Chicago’s thriving food scene, from deep-dish pizza to loaded hot dogs.
With wheelchair accessibility and free cancellation, this tour offers a well-rounded exploration of the Windy City.
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Skip-the-Line Art Institute of Chicago Semi-Private Tour
The Skip-the-Line Art Institute of Chicago Semi-Private Tour offers visitors a comprehensive and efficient way to explore the museum’s world-renowned collection.
With a maximum group size of 8 participants, this 2.5-hour tour provides an intimate and customized experience. Guests will discover notable works by artists like Picasso, Chagall, and O’Keeffe, as knowledgeable guides share captivating stories that enhance understanding of the art.
The tour includes all entrance fees, and the skip-the-line access ensures efficient use of time. While not wheelchair accessible, the tour is suitable for those with moderate physical fitness.
With a 5.0 rating and positive reviews, this tour is an excellent choice for art enthusiasts seeking an informative and enjoyable exploration of the Art Institute of Chicago.
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Chicago: Customizable Private Sightseeing Tour
Explore Chicago’s iconic landmarks and picturesque scenery on a customizable private sightseeing tour.
This 2-hour tour allows you to create an itinerary tailored to your interests, showcasing the city’s must-see attractions. Ideal for up to 3 participants, the tour includes a private vehicle and a knowledgeable local driving guide who can provide insights in English or Yoruba.
Highlights may include stops at Wrigley Field, Millennium Park, and the Chicago Cultural Center, as well as drive-bys of landmarks like The Magnificent Mile and Grant Park.
With free cancellation up to 24 hours in advance and no upfront payment required, this tour is a flexible and convenient way to discover Chicago.
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Private 45-Minute Chicago Skyline Helicopter Tour
From the Schaumburg Regional Airport, travelers can embark on a private 45-minute helicopter tour that offers a bird’s-eye view of Chicago’s iconic skyline.
This experience, rated 4.8 out of 5 based on 120 reviews, accommodates up to three people and includes noise-cancelling headsets, live commentary, and complimentary photos.
Soaring over Millennium Park, Navy Park, Wrigley Field, the John Hancock Center, and the Willis Tower, the tour provides stunning aerial perspectives of the city’s most renowned landmarks.
With a weight limit of 260 lbs per passenger and free cancellation up to 24 hours prior, this private tour ensures a memorable and customizable experience for travelers seeking an aerial adventure in Chicago.
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Chicago: Private Custom Tour With a Local Guide
A private custom tour with a local guide offers visitors an intimate encounter with Chicago’s diverse neighborhoods and renowned landmarks. Priced from $116.11 per person, the tour can last 2 to 8 hours and is available in English and Spanish.
Guests can explore the city’s top sights and hidden gems, with a flexible itinerary tailored to their interests. Transportation isn’t included, but pickup from central hotels is available.
With an overall rating of 4.5/5 from 22 reviews, the tour provides valuable insights into the city’s culture and history from knowledgeable local guides.
Booking in advance is recommended to secure desired dates and plan any additional attraction tickets.
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Chicago River Architecture and History by Private Boat Tour
Traversing the storied Chicago River offers visitors a captivating exploration of the city’s renowned architectural landscape.
Cruising along the waterways, guests can admire the iconic skyscrapers and historical buildings that line the riverbanks. From the 45-minute family-friendly tour to the 1.5-hour guided architecture cruise, these private boat excursions provide an immersive experience.
Passengers can learn about the city’s rich history and marvel at the diverse styles of architecture, ranging from neo-Gothic to modernist.
Whether seeking a quick introduction or a more in-depth exploration, these private river tours cater to a variety of interests and preferences, allowing travelers to discover Chicago’s architectural wonders from a unique vantage point.
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Chicago Loop Architecture Private Walking Tour
Designed for architecture enthusiasts and novices alike, the Chicago Loop Architecture Private Walking Tour offers a captivating exploration of the city’s renowned skyline.
Priced at $227 per person, this 3-hour guided excursion takes participants through the iconic buildings of the Loop, including the Marquette Building, the Sullivan Center, and the Tribune Tower.
Along the way, knowledgeable local experts provide historical insights into the architectural influences that have shaped Chicago’s skyline, from the birthplace of the modern skyscraper to some of the oldest high-rises in the world.
With optional stops, a personal photographer, and free cancellation up to 24 hours in advance, this tour promises an enriching and memorable experience for visitors.
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Chicago Historic Pullman Company Town Private Walking Tour
Immersing visitors in the captivating history of Chicago’s industrial past, the Chicago Historic Pullman Company Town Private Walking Tour takes guests on a captivating 4-hour journey to the Pullman neighborhood.
Priced at $270 per person, the tour includes train tickets, an English-speaking guide, entrance fees, lunch, and bottled water.
Highlights include the Hotel Florence, Historic Pullman Visitor Center, and Greenstone United Methodist Church.
Guests will explore the well-preserved Pullman Historic District, learn about George Pullman’s industrial legacy, and experience the unique culture and architecture of this off-the-beaten-path destination.
With a maximum of 24-hour cancellation for a full refund, this tour offers a comprehensive and personalized exploration of Chicago’s industrial history.
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Chicago Downtown Highlights Private Walking Tour
What better way to experience the heart of Chicago than the Chicago Downtown Highlights Private Walking Tour? Priced at €255.80 per person, this 4-hour guided exploration takes visitors through the city’s iconic landmarks, including Millennium Park, the Marshall Field and Company Building, and the Chicago Cultural Center.
Along the way, a knowledgeable local guide provides insights and acts as a personal photographer, capturing memorable snapshots. The tour is customizable based on participant requests and includes round-trip transportation from hotels.
Whether you’re seeking to learn about Chicago’s vibrant architecture, art, or culture, this private walking tour offers an engaging and personalized experience.
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Chicago: Private Guided Tour of Chicago Suburbs Movie Sites
This private guided tour takes visitors on an immersive journey through the iconic movie locations scattered across Chicago’s vibrant suburbs.
For $6,464 per person, guests can explore 25 filming sites from beloved films like Ferris Bueller’s Day Off and The Breakfast Club.
Led by a local actor, the 3-hour excursion provides fascinating behind-the-scenes insights. Highlights include visiting the infamous Green Mill and Camerons’ house from Ferris Bueller.
Comfortable transportation and gratuities are included. While reviews are mixed, this tour offers a unique opportunity to step into the cinematic world of Chicago’s suburbs.
The tour operates rain or shine, and guests can stay for drinks at the end at their own expense.
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Chicago: Private Helicopter Tour of Chicago Skyline
A thrilling private helicopter tour offers visitors an unparalleled perspective of Chicago’s iconic skyline.
The 10-20 minute flight allows guests to marvel at the city’s renowned landmarks, including the Willis Tower, Navy Pier, and Soldier’s Field.
Soaring high above the Chicago River, passengers can capture one-of-a-kind photos while enjoying live commentary from the experienced pilot.
Priced from €177.64 per person, this exclusive tour is likely to sell out quickly.
Travelers can conveniently reserve their spot and pay later, with the added flexibility of free cancellation up to 24 hours in advance.
With a weight limit of 590 lbs, this weather-dependent experience provides an exhilarating and memorable way to explore the Windy City.
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Chicago: Private Architecture Tour – 3 or 6 Hours
Exploring Chicago’s architectural marvels through a private guided tour, visitors can enjoy the city’s rich design heritage.
Offering both 3-hour and 6-hour options, the tour allows travelers to customize their experience and discover iconic buildings like the Sears Tower, John Hancock Center, and Wrigley Building.
With the extended tour, visitors can also venture to Oak Park to explore Frank Lloyd Wright‘s renowned designs, including the Unity Temple.
Led by expert guides, the tours provide insights into the city’s architectural history and offer exclusive access to both exterior and interior spaces.
Priced at $780 per group, the tour includes hotel pickup, luxury transportation, and optional stops for famous local cuisine.
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Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour
Promising to whisk guests back in time, the Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour invites travelers to experience the hidden gems of the city’s notorious Prohibition Era.
Priced at $950 for up to 5 participants, the 3-hour private tour grants exclusive access to historic speakeasies via secret passages. Guests can savor Prohibition-era cocktails while learning about the era’s gangsters and racketeering from a young, local historian.
The tour includes pickup and drop-off within Chicago, as well as luxury transportation options. Not suitable for those under 21 or with mobility issues, the tour requires a passport or ID.
With an impressive 5/5 rating based on 6 reviews, this immersive experience promises an unforgettable glimpse into Chicago’s captivating past.
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The Sum Up
Chicago offers a variety of private tour options for visitors to explore the city’s renowned architecture, cuisine, and cultural highlights. From guided walking tours of the Loop to helicopter rides over the skyline, there’s a customized experience to suit every interest. Whether you’re a first-time traveler or a seasoned local, these private tours provide an exclusive and immersive way to discover the best of what Chicago has to offer.