Top Chicago Private Sightseeing Tours - page 3

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Chicago Private Night Skyline and Lakefront Scenic Tour

Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour. Travel in comfort with your English-speaking driver, who shares stories and insights about the city’s architecture, neighborhoods, and history as the skyline comes alive after sunset. Begin along the Magnificent Mile, where illuminated skyscrapers and elegant streets create a stunning urban scene. Continue to the Chicago River for reflections of iconic buildings, then visit Navy Pier with its sparkling Ferris wheel and waterfront views. Drive along Lake Shore Drive to admire the dramatic skyline over Lake Michigan, and finish at Adler Planetarium for one of the city’s most spectacular panoramic night views. This flexible, door-to-door private tour offers a relaxed, immersive way to enjoy Chicago’s landmarks and lakefront illuminated under the night sky.

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Chicago Private Night Skyline and Lakefront Scenic Tour

2 hoursFree Cancellation

Price varies by group size

Member Pricing

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

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

Price varies by group size

Member Pricing

Bucktown and Wicker Park’s 606 Trail: A Walking Tour

The Bloomingdale Trail was built on a former railway line that once served as the industrial backbone of Chicago's north side. On this self-guided audio tour through Bucktown and Wicker Park, you'll hear how the factories, immigrants, and artists who lined these tracks transformed two scrappy neighbourhoods into some of the city's most sought-after real estate. The tour starts at Walsh Park, the eastern terminus of The 606, named with a nod to Chicago's universal zip code prefix. Further along, you'll stop at the Damen Avenue Arts Plaza, where the Flat Iron Arts Building stands as a reminder of how artists were deliberately recruited to revive a struggling neighbourhood. The tour ends at Western Avenue, the longest continuous city street in the world at 24.5 miles, where the trail continues west into Logan Square and Humboldt Park.

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Bucktown and Wicker Park’s 606 Trail: A Walking Tour

30 minutes to 1 hourFree Cancellation

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

from $144

Member Pricing

Private Wicker Park and Bucktown Walking Tour

2 hours 30 minutesFree Cancellation

Member Pricing

Admire a side of Chicago that few other visitors get to experience—and enjoy a relaxing trip out on the water, tailored to your party—with this private sailboat charter and sailing tour. You and up to five other guests will have the exclusive use of a sailboat, complete with a captain for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you can even take a turn at the helm.

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Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

2 hoursFree Cancellation

Member Pricing

Discover Chicago’s infamous gangster past on a private, fully personalized tour through the city’s historic Prohibition-era streets. Travel in comfort with your English-speaking driver, who shares captivating stories about Al Capone, rival gangs, speakeasies, and legendary crime events of the 1920s and 1930s. Begin at Biograph Theater, where John Dillinger was shot, then visit the St. Valentine’s Day Massacre site, a pivotal moment in Al Capone’s rise. Explore Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray’s Italian Steakhouse, all linked to Chicago’s mob history. Conclude in the Chicago Loop, uncovering hidden speakeasies and secret nightlife spots from the Prohibition era. With a flexible, door-to-door itinerary, this private tour offers an immersive, thrilling look into the city’s dramatic gangster history.

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Chicago Gangsters and Prohibition Private History Tour

2 hoursFree Cancellation

Price varies by group size

Member Pricing

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal guide! Enjoy all the Holiday sites the city is known for including, Daley Plaza's Christkindl Market, Macy's Walnut Room and animated story windows, the Goodman Theatre, and marvel at the skaters under the iconic "Bean" of Millennium Park. This experience is the only way to see Chicago during the holidays!

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Private Holiday City Tour

3 hoursFree Cancellation

Member Pricing

Bucktown has a knack for keeping secrets - and most of them are deeply unsettling. On this self-guided walking tour, you'll hear the true stories behind the neighborhood's murders, hauntings, and disappearances, encountering a real-life fugitive, the ghost of a pub owner who still tends bar, and a winged creature with red eyes spotted across Chicago. Starting at the former Lincoln Tavern, where a 1980 robbery ended in multiple murders, you'll pass the spot where a 12-year-old boy was killed by a train in 1902. You will see where residents still report signs of his presence, and walk by the only Opus Dei-operated church in the country. The tour ends at Club Lucky, where three bullet holes still visible in the bar mark the spot where a Polish immigrant named Walter met his unfortunate end in January 1967. Sweet dreams.

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Dark Tales of Bucktown: A Self-Guided Chicago Tour

40 minutes to 1 hour 20 minutesFree Cancellation

Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO

1 to 30 days

4.0

(370)

from $84

Member Pricing

Enjoy a private pedicab tour through Lincoln Park with your friends, family or partner- every tour is customized to what your party wants to see and do!

Discover the hidden gems of Lincoln Park on a private, open-air pedicab ride guided by a local storyteller. Relax as you explore lush gardens, the iconic lily pond, lakefront views, and landmark architecture— all without the effort of walking or the crowds of bus tours. Your route and pace are fully customizable, with plenty of photo stops and personal stories that bring Chicago’s past to life. Perfect for families, visitors with mobility needs, photography lovers, or anyone seeking a breezy, memorable Chicago adventure.

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Lincoln Park Secrets: Private Enchanted Pedicab History Tour

1 hour to 1 hour 10 minutesFree Cancellation

Price varies by group size

Member Pricing

Logan Square Walking Tour Experience

1 hour 20 minutesFree Cancellation

5% savings

from

$35$33

Member Pricing

Private Magnificent Mile Architecture Tour and 360 Chicago Ticket

2 hoursFree Cancellation

Price varies by group size

Member Pricing

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians who made up what was known as the “Chicago Outfit” • Hear from producer Richard Junger, an urban historian, professor and author passionate about Chicago • Do it all in 45 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code. The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.

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Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

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Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat for the elite to a vibrant, diverse community shaped by migration, policy, and social change. Explore iconic landmarks like the Museum of Science and Industry while gaining insight into the impacts of racial segregation and urban renewal. This tour is designed for history buffs and urban studies enthusiasts, offering a nuanced perspective on the intersection of race and community development. - Walk through Hyde Park and learn about its historical significance - Visit key sites related to civil rights and urban policy - Understand the neighborhood's transformation and ongoing challenges - Perfect for history lovers and those curious about social dynamics

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Hyde Park Walking Tour History Race and Urban Change

3 hoursFree Cancellation

5% savings

from

$5$5

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Exclusive Downtown Chicago Guided Walking Tour 12ppl Max

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

Price varies by group size

Member Pricing

Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

Channel your inner detective on this immersive, self-guided scavenger hunt through Chicago’s Loop! Step back to 1923 as you gather clues, solve a murder mystery, and unlock secrets of Prohibition-era Chicago. Your group receives a mystery kit, then follows a story-driven trail at your own pace—no app required. Observe real landmarks and hidden clues as you work together, making this ideal for friends, families, and groups seeking a hands-on, flexible adventure. The perfect blend of history, teamwork, and local intrigue in the heart of Chicago.

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Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

1 hourFree Cancellation

Member Pricing

It isn’t a trip to Chicago without tasting deep-dish pizza—and this private tour for food lovers will introduce you to true Chicago-style pizza, plus other Windy City specialties. Meet your guide downtown, and be sure to come hungry: You’ll eat hot dogs, Italian beef sandwiches, pizza, donuts, and more. Along the way, see highlights like the Wrigley Building and Magnificent Mile, and learn more about the city’s history and culture.

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Private Chicago Foodie Tour

4 hoursFree Cancellation

Member Pricing

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic skyscrapers and stunning lobbies, learning the fascinating stories behind their designs. This 2.5-hour tour is perfect for architecture enthusiasts and curious travelers alike, providing a unique perspective on the birthplace of modern skyscrapers. Whether you’re a local or a visitor, discover why Chicago's skyline is renowned worldwide. - Private tour lasting 2.5 hours, perfect for families and small groups - Visit landmark buildings like The Sullivan Center and The Rookery - Expert local guide shares insider knowledge about architectural history - Flexible meeting points available for your convenience

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Private Chicago Loop Architecture Walking Tour

2 hours to 2 hours 30 minutesFree Cancellation

Price varies by group size

Member Pricing

Downtown Chicago Loop Walking Tour (Private)

Discover the stories, styles, and spirit that built Chicago into the architectural capital of the world. On this walking tour through the Loop, you’ll explore the birthplace of the skyscraper, visit landmarks like the Chicago Theatre, the Pablo Picasso at the Daley Plaza, and Millennium Park, and see how the city rose from the Great Fire to define modern design. Led by a friendly local guide who’s passionate about Chicago’s history and architecture, this tour brings the skyline to life one building, story, and photo stop at a time. Whether you’re an architecture enthusiast, a first-time visitor, or a curious local, you’ll walk away seeing Chicago in a whole new way.

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Downtown Chicago Loop Walking Tour (Private)

2 hoursFree Cancellation

5% savings

from

$27$26

Member Pricing

Chicago Highlights Private Walking Tour with a Guide

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey by marveling at the grandeur of the Wrigley Building, followed by a step into the opulence of the Palmer House Hilton lobby. Admire the sleek lines of the Carbide and Carbon Building, a testament to Art Deco elegance, before appreciating the historic significance of the Reliance Building. Conclude your architectural odyssey with a visit to the exquisite Chicago Cultural Center, a masterpiece of design and culture. Throughout the tour, your knowledgeable guide illuminates Chicago's rich history and architectural evolution, weaving captivating stories that offer insight into the city's vibrant past and enduring legacy.

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Chicago Highlights Private Walking Tour with a Guide

2 hoursFree Cancellation

Price varies by group size

Member Pricing

Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game

Venture along Michigan Avenue on an interactive tour to uncover Chicago's hidden gems and iconic landmarks. Dive into the city's rich history, answer trivia, and complete challenges for a unique experience blending sightseeing with gaming. Explore the Magnificent Mile and Cultural Mile with this unique adventure: Solve puzzles, explore the city, and find hidden gems at your own pace. Try a new type of experience with your smartphone, the perfect mix between a walking tour, sightseeing, and a scavenger hunt.

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Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game

1 to 2 hoursFree Cancellation

5% savings

from

$17$16

Price varies by group size

Member Pricing

Private and All-Inclusive Tour of Chicago

Whether you’re a first-time visitor or are just looking for a stress-free way to sightsee, this private, full-day driving tour makes discovering Chicago’s top sights simple. Meet your guide in the morning at your hotel, and set off: see landmarks like Wrigley Field, Grant Park, Millennium Park (and “the Bean”) all in one day. Don’t forget to bring your phone or camera to capture memorable snaps en route.

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Private and All-Inclusive Tour of Chicago

6 hoursFree Cancellation

Member Pricing

Skip the lines to the iconic Art Institute of Chicago and marvel at world-famous masterpieces by Monet, Van Gogh, and Picasso. Dive into a treasure trove of art, history, and culture at one of the oldest and most celebrated museums in the U.S. Tour is available in following language: English Spanish & French Highlights: • Private Tour of the Art Institute of Chicago • 5-Star Licensed Guide fluent in your chosen language • Skip-the-Line Tickets to the Art Institute of Chicago • Insightful stories about world-famous masterpieces, including works by Monet, Van Gogh, and Picasso • Expert guidance through Impressionist, Post-Impressionist, and Modern Art collections Discover the rich art and cultural heritage of Chicago with Rosotravel on an exclusive private tour with Skip-the-Line Tickets to the iconic Art Institute. Enjoy the luxury of a personalized itinerary led by a Licensed Private Guide. Uncover the magic of Chicago’s artistic treasures today!

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Skip-the-Line Art Institute of Chicago Private Guided Tour

2 hoursFree Cancellation

Price varies by group size

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Must-Dos in Chicago

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Top Chicago Private Sightseeing Tours - page 3

100+ results

Must-Dos in Chicago

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

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