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Chicago City Private Tours

41 Reviews 4.76 out of 5 stars Based on 41 reviews collected by City Sky Diving and TripAdvisor |
Recommended by 93% of reviewers
93% of reviewers gave this experience a rating of 4 or higher.
|
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards. Chicago, USA
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from $199 per group (up to 4)

Lowest Price Guarantee
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Don't miss out!
On average, this is booked 16 (0) days in advance.
2 to 8 hours (approx.)
Hotel pickup offered
Mobile ticket
Offered in: English
and 2 more
French, Arabic
Instant confirmation

Overview

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a unique and unforgettable experience, customizable from 2 to 8 hours. From the iconic skyline to hidden gems off the beaten path, I’ll take you on a journey that captures the heart and soul of this incredible city. I’ll also capture professional photos along the way, so you can take home memories of your adventure. With flexible pickup options, including quick tours during layovers at O'Hare, I make it easy to see the best of Chicago, no matter how much time you have. Book your tour today and let me show you the Windy City through the eyes of a local!

What's Included

  • Snacks
  • Bottled water
  • Private transportation
  • Gratuities
See 3 moreSee 2 more

Meeting and Pickup

Pickup point
Pickup details

I offer flexible pickup locations to make your experience as convenient as possible. Whether you're staying in downtown Chicago, a vibrant neighborhood, or even have a layover at O'Hare Airport, I can arrange a pickup that works for you. If you're at O'Hare, I'll customize a quick tour to help you make the most of your time, ensuring you get back to your flight stress-free. Just let me know where you’re located, and I’ll ensure a smooth, memorable start to your tour!

What To Expect

Book Online

Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
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Safe & secure Easy breezy Hassle‑free

Holy Name Cathedral

Holy Name Cathedral, built in 1875, is the historic seat of the Archdiocese of Chicago and one of the city’s most beautiful churches. Known for its stunning Gothic Revival architecture, stained-glass windows, and peaceful interior, it stands as an important landmark rebuilt after the Great Chicago Fire of 1871.
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10 minutes Admission Ticket Free

360 Chicago Observation Deck

Panoramic Views: Stunning 94th-floor views of Chicago and Lake Michigan. TILT Experience: Lean out over the city in a glass platform for a thrilling view. Interactive Displays: Learn about Chicago's history and landmarks. Observation Decks: Both indoor and outdoor areas for 360-degree views. Photo Opportunities: Great spots for capturing city views
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45 minutes Admission Ticket Free

The Magnificent Mile

A premier shopping district along Michigan Avenue, lined with luxury boutiques, historic landmarks, and renowned eateries.
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1 minute Admission Ticket Free

Chicago Riverwalk

Scenic Views: Enjoy stunning views of the Chicago River and iconic architecture. Walking and Biking: Ideal for strolling or biking along the water. Boating: Rent kayaks or take a river cruise to see the city from the water. Dining: Outdoor restaurants, cafes, and bars along the river. Public Art: Discover art installations and sculptures throughout the Riverwalk. Events: Live music, festivals, and entertainment depending on the season. Relaxation: Enjoy quiet spots to sit, relax, and take in the riverfront atmosphere.
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20 minutes Admission Ticket Free

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Rooftop is a popular upscale rooftop bar located at the top of the historic LondonHouse hotel on the Chicago River. It offers panoramic views of the city skyline, the river, and iconic landmarks like the Wrigley Building and Tribune Tower, making it a top stop for photos and sightseeing in downtown Chicago.
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15 minutes Admission Ticket Free

The Chicago Theatre

An iconic venue hosting concerts, plays, and special events in a historic setting.
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1 minute Admission Ticket Free

Chicago Cultural Center

A stunning architectural gem hosting free art exhibitions, performances, and public events.
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10 minutes Admission Ticket Free

Millennium Park

Cloud Gate (The Bean): Visitors will see the iconic reflective sculpture, perfect for photos with the Chicago skyline. Crown Fountain: An interactive water feature with video projections and playful water sprays. Jay Pritzker Pavilion: A stunning outdoor amphitheater, often hosting free concerts and events. Lurie Garden: A peaceful garden offering a scenic spot to relax amidst beautiful landscaping. Interactive Activities and Events: Temporary exhibits and cultural events to engage with during their visit. Biking and Walking: Nearby paths for biking or walking to explore the lakefront and nearby areas. Food and Shopping: A variety of food options and shops for a complete experience. Learn About the History: Opportunities to discover the park's history and cultural significance.
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25 minutes Admission Ticket Free

The Art Institute of Chicago

One of the oldest and largest art museums in the U.S., housing an extensive collection spanning centuries and cultures.
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1 minute Admission Ticket Free

Palmer House Hilton Historic Lobby

Originally opened in 1871 as a wedding gift from Potter Palmer to his bride Bertha Honoré, the hotel was rebuilt after the Great Chicago Fire and has since become a symbol of resilience and luxury. It holds the distinction of being North America's longest-operating hotel.
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1 minute Admission Ticket Free

Marquette Building

The Marquette Building, located at 140 S. Dearborn Street in Chicago’s Loop, is a celebrated example of early skyscraper design and a cornerstone of the city’s architectural heritage
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10 minutes Admission Ticket Free

The Rookery Building

The Rookery Building remains a cherished piece of Chicago's architectural heritage, reflecting the city's innovative spirit and historical depth.
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1 minute Admission Ticket Free

Chicago Board Of Trade Building

The Chicago Board of Trade Building is a historic Art Deco skyscraper completed in 1930 and one of the most iconic landmarks in the Chicago Loop. It was the longtime home of the world’s oldest futures and options exchange, symbolizing Chicago’s role as a global financial center. The building is especially known for its striking statue of Ceres, the Roman goddess of agriculture, at its top.
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5 minutes Admission Ticket Free

Chicago Fed's Money Museum

The Money Museum at the Federal Reserve Bank of Chicago is a free museum that explores the history of money, banking, and the U.S. economy. Visitors can view exhibits on currency, see a real cash-processing area, and even lift a bag containing $1 million in $1 bills.
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15 minutes Admission Ticket Free

Skydeck Chicago - Willis Tower

Panoramic Views: Stunning views from the 103rd floor of the Willis Tower. The Ledge: A glass-floored balcony extending outside for a thrilling view straight down. Interactive Exhibits: Learn about Chicago’s history and architecture. Souvenirs: Unique Chicago-themed gifts available at the gift shop. Photo Opportunities: Perfect spots for breathtaking photos of the city.
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45 minutes Admission Ticket Free

Union Station

Chicago Union Station stands as a remarkable blend of functionality and architectural beauty, reflecting the city's rich history and its pivotal role in America's transportation network.
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10 minutes Admission Ticket Free

Chinatown

Chicago’s Chinatown is a vibrant cultural district known for its traditional Chinese architecture, authentic restaurants, shops, and the iconic Chinatown Gate on Wentworth Avenue. It’s a popular stop for visitors looking to experience cultural food, history, and colorful street scenery just south of downtown.
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15 minutes Admission Ticket Free

Jackson Park's Japanese Garden

A historic park on the South Side, home to the Museum of Science and Industry and beautiful lagoons.
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1 minute Admission Ticket Free

Obama Presidential Library (pass by)

The Obama Presidential Center is a future landmark in Jackson Park dedicated to President Barack Obama’s legacy. It will include a museum, public gardens, and community spaces designed to highlight civic engagement, education, and Chicago’s South Side history.
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Frank Lloyd Wright Trust - Frederick C. Robie House Tour

A Frank Lloyd Wright masterpiece located in Hyde Park, exemplifying Prairie School architecture.
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1 minute Admission Ticket Free

University of Chicago

a must-see destination for visitors to the city. Its beautiful campus blends Collegiate Gothic architecture with striking modern buildings, set among tree-lined quads and lush gardens. Highlights include the Rockefeller Memorial Chapel, the iconic Harper Library, and the Robie House—an architectural masterpiece by Frank Lloyd Wright.
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10 minutes Admission Ticket Free

Museum Campus

A scenic lakefront area encompassing the Field Museum, Shedd Aquarium, and Adler Planetarium, offering insights into natural history, marine life, and astronomy.
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1 minute Admission Ticket Free

Field Museum

World-Class Exhibits: Explore natural history exhibits, including fossils, ancient civilizations, and rare artifacts. Sue the T. rex: See the famous and largest T. rex skeleton ever discovered. Interactive Displays: Engage with hands-on exhibits and educational programs. Cultural Exhibits: Learn about global cultures through diverse collections from around the world. Family-Friendly: Features activities and exhibits designed for all ages, making it great for families. The Field Museum offers a fascinating journey through science, history, and culture, with iconic exhibits like Sue the T. rex and engaging displays for all ages.
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40 minutes Admission Ticket Free

Clarence F. Buckingham Fountain

Buckingham Fountain is one of Chicago’s most famous landmarks, located in Grant Park. Built in 1927, it is one of the largest fountains in the world and features dramatic water displays set against the backdrop of the city skyline and Lake Michigan. It’s especially popular for photos and shows during the warmer months.
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10 minutes Admission Ticket Free

Navy Pier

A bustling entertainment hub featuring a 15-story Ferris wheel, theaters, restaurants, and seasonal events, drawing approximately 8 million visitors annually
Read more

1 minute Admission Ticket Free

Lincoln Park Conservatory

The Lincoln Park Conservatory is a historic glass greenhouse located in Lincoln Park, built in the late 1800s. It features beautifully maintained indoor gardens with tropical plants, orchids, ferns, and seasonal floral displays, offering a peaceful escape from the city year-round.
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20 minutes Admission Ticket Included

Lincoln Park

Free Admission: Explore one of the oldest and most popular free zoos in the U.S. Wildlife Exhibits: See a wide variety of animals, including lions, gorillas, and penguins. Historic Conservatory: Visit the Lincoln Park Conservatory with beautiful plant displays and seasonal flowers. Beautiful Gardens: Stroll through well-maintained gardens, perfect for relaxation and photography. Family-Friendly: Enjoy activities and exhibits suitable for all ages, making it a great spot for families. Lincoln Park Zoo and Conservatory offer a mix of wildlife encounters, lush gardens, and family-friendly experiences, all in a scenic, accessible setting.
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40 minutes Admission Ticket Free

Elks National Memorial

The Elks National Memorial is a grand neoclassical monument honoring members of the Benevolent and Protective Order of Elks who served in World War I. Completed in 1926, it features a massive dome, intricate marble interiors, and impressive murals and sculptures. It’s one of Chicago’s hidden architectural gems located near Lincoln Park
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10 minutes Admission Ticket Free

Wrigley Field

Iconic Ballpark: Visit one of the oldest and most famous baseball stadiums in the U.S. Chicago Cubs Experience: Watch a Chicago Cubs game or tour the stadium. Historic Atmosphere: Explore the rich history and tradition of Wrigley Field, including its ivy-covered outfield wall. Museum and Exhibits: Learn about the Cubs’ legacy through displays and memorabilia. Photo Opportunities: Capture iconic shots of the field, scoreboard, and vintage features.
Read more

20 minutes Admission Ticket Free

Trump International Hotel & Tower® Chicago

outdoor dining and riverfront area at the base of the Trump International Hotel & Tower along the Chicago River. It’s a popular photo stop offering close-up views of the riverwalk and surrounding skyline, especially the Wrigley Building and Michigan Avenue Bridge.
Read more

10 minutes Admission Ticket Free

Show 29 more stops

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Specialized infant seats are available

Frequently Asked Questions (8)

Q: What is the cancellation policy for the Chicago City Private Tours?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CST). Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-5545076P1

Traveler Photos

Reviews

4.76
41 reviews

Average 4.76 out of 5 stars based on 41 traveler reviews collected by City Sky Diving and partner sites such as Cool Destinations and TripAdvisor

5 stars
37
4 stars
1
3 stars
1
2 stars
1
1 star
1
Don't miss out!
On average, this is booked 16 (0) days in advance.
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Frequently Asked Questions (8)

Activity name

The answers provided below were previously given in response to questions from City Sky Diving customers.

Filter by:

Q: What is the cancellation policy for the Chicago City Private Tours?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (CST).
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Snacks.
  • Bottled water.
  • Private transportation.
  • Air-conditioned vehicle.
  • Fuel surcharge.
  • Parking Fees.
The following is NOT included:
  • Gratuities.
Apr 2025
Q: What is the weather cancellation policy?
A:

This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Chicago City Private Tours is as follows:

  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Chicago City Private Tours will be included in your confirmation email from City Sky Diving. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024
Q: How long does a refund take to reach my card, and can I get it faster?
A:

Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

Oct 2026

What's Included

Activity name

  • Snacks
  • Bottled water
  • Private transportation
  • Air-conditioned vehicle
  • Fuel surcharge
  • Parking Fees
  • Gratuities

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Specialized infant seats are available

Report Product Issue

Activity name