Top Chicago Private Sightseeing Tours - page 4

Private Sightseeing Tours

100+ results

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(2)

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

4 hoursFree Cancellation

from $236

Luxury Sedan- Lincoln Continental, Cadillac XTS, Lincoln MKT or similar

If it’s your first time in Chicago or you just have limited time, make the most of a day in the Windy City on a private driving tour. Instead of navigating public transit or waiting for ride shares, relax as a dedicated driver takes you to all the major attractions of downtown and beyond, including Navy Pier, Michigan Avenue, Wrigley Field, Millennium Park, and Museum Campus. Plus, get local insight into Chicago along the way.

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Chicago 6-Hour City Tour by Sedan

6 hoursFree Cancellation

from $960

Per group

Likely to Sell Out

This is not a bus tour, 90% of our tours are 11 people or less, as we specialize in small, personalized group tours. This gives us the space and time to take pictures and have great conversation! The personal, small tour approach allows travelers to have a personal tour experience of the city. With our small tour there are opportunities for questions and non-scripted conversations. A true experience. We have additional tours that accommodate large groups but this tour is geared towards sights and fluid conversations about the black starts of Chicago! The guide will take photos for you while educating you on the city and it's historical residents. On the Chicago Soul House tour, travelers tour the South Side of Chicago and can see the homes of the city's stars. The antidotes and stories are being told by someone who sang at the same lounges as Jennifer Hudson, played with Muhammad Ali as a child and traveled to Chicago during the Great Black Migration.

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3.8

(4)

2 Hour Private Chicago Soul House Tour

2 hoursFree Cancellation

from $65

Likely to Sell Out

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. Tour Chicago in a small group perfect for busy sidewalks and get up close to monumental art! Join one of our expert guides on this unique and exclusive 2.5 hour guided walking tour of Downtown Chicago. Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

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Exclusive Downtown Chicago Guided Walking Tour 12ppl Max

2 hours 30 minutesFree Cancellation

from $52

Price varies by group size

Logan Square Walking Tour Experience

1 hour 20 minutesFree Cancellation

from $35

Chicago is renowned for its architecture—and this immersive walking tour offers the perfect way to discover its highlights. Pick from a wide range of start times, meet your private guide right in the Loop, and set off on foot. In between seeing renowned landmarks like the Chicago Cultural Center, public art by Picasso, and other heritage buildings, you’ll learn all about the city’s history.

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Private 2-Hour Walking Tour: Chicago Loop Interior Architecture

2 hours

from $324

Price varies by group size

Route 66, known as "The Main Street of America", runs through eight states from Chicago to Santa Monica. EN route to Illinois, POR Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. Along DE way, it connects iconic cities such as St. Louis, Tulsa, Amarillo, Albuquerque, Flagstaff and Los Angeles, offering a unique experience through varied landscapes, from the Midwest Plains to the Southwest Deserts, each with its own history and culture. Route Chicago : 50 points Route DE Chicago to St. Louis : 56 points Route San Luis : 13 points Route DE San Luis to Joplin : 56 points Route Joplin to Oklahoma city : 29 points Route DE Oklahoma City to Amarillo : 27 points Yellow Route to Santa Fe : 39 points Route DE Santa Fe to Las Vegas : 80 points Route DE Las Vegas to Los Angeles : 34 points Total DE DE DE DE l’Or points of interest: 384

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Routes POR Route 66 with Audio Guide

6 daysFree Cancellation

from $24

Per group

5.0

(3)

Private Wicker Park and Bucktown Walking Tour

2 hours 30 minutesFree Cancellation

from $195

Per group

5.0

(13)

Private Chicago History Museum Tour

2 hoursFree Cancellation

from $163

Price varies by group size

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are illuminated with festive displays. How do European holiday customs shape winter traditions in American cities? Along State Street, seasonal décor reflects a long-standing retail heritage. The Christkindlmarket introduces a cultural tradition rooted in German history and craftsmanship. Wooden stalls and artisan goods echo centuries-old holiday markets of Europe. This experience blends festive atmosphere with cultural continuity in a refined city setting. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

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5.0

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Private Christmas Walking Tour in Chicago with Christkindlmarket

2 hoursFree Cancellation

from $723

Price varies by group size

Likely to Sell Out

Enjoy a private, fully personalized sunset tour along Chicago’s scenic lakefront. Travel in comfort with your English-speaking driver, who shares insights into the city’s architecture, skyline, and history while guiding you to the best photo spots. Begin at Museum Campus, where the skyline rises above Lake Michigan, offering stunning reflections at golden hour. Continue to Adler Planetarium for one of Chicago’s most iconic panoramic skyline views. Visit Buckingham Fountain, where the historic landmark creates a beautiful foreground for sunset photos. Head to North Avenue Beach to capture the skyline stretching across the horizon as the sun sets, then enjoy a scenic drive along Lake Shore Drive as city lights begin to glow. With a flexible itinerary and door-to-door service, this experience offers a relaxed, unforgettable way to capture Chicago’s skyline from day to night.

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Chicago Private Lakefront Sunset and Skyline Photo Tour

2 hoursFree Cancellation

from $145

Price varies by group size

4.3

(6)

Private Frida and Friends Tour in Pilsen

2 hoursFree Cancellation

from $240

Per group

Chicago is inseparable from its Black history, where local pioneers helped shape the city’s story. On this self-guided audio tour through downtown Chicago, you’ll hear untold stories of Black excellence, resilience, and activism that transformed both the city and the nation. From Underground Railroad stations to civil rights battlegrounds, you’ll discover how Chicago became a beacon for those seeking freedom and opportunity. Starting at the site of Jean Baptiste Point DuSable’s mansion near the Chicago River, you’ll follow the footsteps of the city’s founder: a Black man who established Chicago’s first trading post in the 1770s. You’ll walk through the heart of the Loop, exploring sites where pioneering entrepreneurs like John Jones built businesses that became platforms for activism. The tour ends at Grant Park, where Barack Obama delivered his historic presidential acceptance speech in 2008 – a moment that represented the culmination of generations of struggle.

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Resilience and Revolution: Audio Tour of Chicago’s Black History

2 hours to 2 hours 30 minutesFree Cancellation

from $15

It would take days to visit all of Chicago’s famous sights, but who has that kind of time? Cover the highlights of the Windy City during this private half-day walking tour. From the Magnificent Mile to Millennium Park, you’ll tick off top attractions while your guide fills you in on Chicago’s history. Finally, enjoy panoramic views overlooking the city from Hancock Tower’s Observation Deck—admission tickets included.

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Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

3 hoursFree Cancellation

from $240

Price varies by group size

Likely to Sell Out

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local stories, historical insights, and highlights the architecture and communities that shape the city’s unique character. Begin in the Gold Coast Historic District with its elegant mansions and tree-lined streets, then explore Lincoln Park with its scenic paths, gardens, and historic zoo. Visit Wrigley Field to experience Chicago’s sports culture, followed by Hyde Park and the University of Chicago, known for its stunning architecture and intellectual heritage. Conclude in Chinatown, a lively cultural district with colorful streets, markets, and traditional restaurants. With a flexible, door-to-door itinerary, this private tour offers a relaxed, immersive way to experience Chicago’s history, culture, and diverse neighborhoods.

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Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

4 hoursFree Cancellation

from $227

Price varies by group size

Comfortable Roundtrip Tour from your hotel in Chicago to Fashion Outlets of Chicago - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

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Private Shopping Tour from Chicago to Fashion Outlets of Chicago

5 hoursFree Cancellation

from $269

Price varies by group size

Comfortable Roundtrip Tour from your hotel in Chicago to Chicago Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

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Private Shopping Tour from Chicago to Chicago Premium Outlets

5 to 6 hoursFree Cancellation

from $296

Price varies by group size

Chicago Private Tour

3 hoursFree Cancellation

from $300

Per group

Immerse yourself in the vibrant food culture of Chicago with a guided walking tour, led by a knowledgeable local guide. Traverse Downtown's diverse culinary landscape, tracing the influence of immigrants on the city's gastronomy. Indulge in the iconic Chicago deep-dish pizza, renowned for its thick crust and flavorful fillings, followed by a visit to a historic eatery for the famed dipped Italian beef sandwich, a local favorite. Amidst culinary delights, marvel at architectural marvels like Cloud Gate and the Chicago Cultural Center, adding depth to your exploration. As the tour unfolds, anticipate a tantalizing surprise: a secret dish, revealed only on the day of your adventure, promising an unexpected culinary delight. This immersive experience offers not only a feast for the palate but also insights into Chicago's rich culinary heritage and architectural splendor.

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Private Chicago Street Food Walking Tour With A Local Guide

3 hoursFree Cancellation

from $309

Price varies by group size

Discover Hollywood magic in the heart of the Midwest on the Chicago Suburbs Movie Sites Tour. Visit real filming locations from classics like Ferris Bueller’s Day Off and Home Alone to modern hits like The Dark Knight. Led by a local actor guide, explore iconic homes, schools, and streets while hearing behind-the-scenes stories and fun film trivia. Perfect for movie lovers and anyone wanting a fresh, cinematic look at the Chicago suburbs.

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Private Chicago Suburbs Movie Sites Tour

2 to 3 hours

from $320

Price varies by group size

Comfortable Roundtrip Tour from your hotel in Chicago to Lighthouse Place Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

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Private Shopping Tour from Chicago to Lighthouse Place Outlets

6 to 7 hoursFree Cancellation

from $376

Price varies by group size

2 hours Private Evening Walking Tour with the Ghosts of Chicago

2 hoursFree Cancellation

from $350

Per group

This private historical ghost walking tour in Chicago explores stories rooted in the city’s layered past. You will walk through Lincoln Park, an area shaped by transformation from cemetery grounds to residential district. What traces of earlier history remain beneath modern streets? Architectural landmarks reflect 19th-century development and urban expansion. Historic venues such as theaters and pubs carry narratives passed through generations. These accounts reveal how memory and place intertwine within the city’s cultural fabric. The experience offers a thoughtful perspective on Chicago’s past through legend and documented history. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

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Private Historical Ghost Walking Tour in Chicago Lincoln Park

2 hoursFree Cancellation

from $663

Price varies by group size

Likely to Sell Out

This private architectural walking tour in Chicago explores residences that reflect the city’s design evolution. You will begin along Lake Shore Drive, where early high-rise living reshaped urban life. What architectural movements defined Chicago’s rise as a global city? Historic homes reveal craftsmanship influenced by leading architects of the modern era. Prestigious streets present a collection of preserved facades that reflect social and cultural history. Landmark residences highlight transitions from classical to modern design principles. This experience offers insight into architectural innovation and the lifestyles that shaped it. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

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Private Architectural Walking Tour in Chicago Historic Residences

2 hoursFree Cancellation

from $663

Price varies by group size

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Top Chicago Private Sightseeing Tours - page 4

100+ results

Top Attractions in Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

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