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!
Prices change with the date; the lowest is shown.
Out at sunset: the 2:30 PM departure is under way when the sun sets, around 4:24 PM in the coming weeks.
From the operator’s live schedule on Viator, checked Nov 12.
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.
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
A premier shopping district along Michigan Avenue, lined with luxury boutiques, historic landmarks, and renowned eateries.
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.
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.
An iconic venue hosting concerts, plays, and special events in a historic setting.
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!
Reviews collected by Viator and Tripadvisor
Excurgo comparison of 517 Viator tours, recalculated daily.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Chicago City Private Tours lasts about 2–8 hours. The itinerary has 30 stops.
Prices start at $199 per person for this Chicago experience, booked through Viator with the price shown before checkout. There are 5 booking options, so the final price depends on the option you choose.
According to the operator’s current schedule, it runs on Mondays, Saturdays, and Sundays, with 25 departures a day between 9:00 AM and 9:00 PM.
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
Yes, pickup is offered. 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! Pickup points include WoodSpring Suites Chicago Darien, Extended Stay America - Chicago - Darien.
The experience is available in AR, EN, FR.
Reviews collected by Viator and Tripadvisor
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
 Chicago City Private Tours | 2–8 hours | 4.6 (38) | $199 | |
 Chicago Private City Tour with Hotel Pick Up | 3–4 hours | 4.9 (211) | $539 | View |
 Private Holiday City Tour | 3 hours | 5.0 (3) | $499 | View |
 Private City Tour 3-5ppl | 3–4 hours | 5.0 (3) | $649 | View |
 Private Chicago Food Tour with Deep Dish and Beef Sandwich | 3 hours | 5.0 (88) | $225 | View |
 Private 45-Minute Chicago Skyline Helicopter Tour | 45 min | 4.8 (134) | $849 | View |
 Private Magnificent Mile Architecture Tour and 360 Chicago Ticket | 2 hours | 4.9 (81) | $235 | View |
A stunning architectural gem hosting free art exhibitions, performances, and public events.
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.
One of the oldest and largest art museums in the U.S., housing an extensive collection spanning centuries and cultures.
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.
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
The Rookery Building remains a cherished piece of Chicago's architectural heritage, reflecting the city's innovative spirit and historical depth.
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.
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.
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.
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.
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.
A historic park on the South Side, home to the Museum of Science and Industry and beautiful lagoons.
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.
A Frank Lloyd Wright masterpiece located in Hyde Park, exemplifying Prairie School architecture.
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.
A scenic lakefront area encompassing the Field Museum, Shedd Aquarium, and Adler Planetarium, offering insights into natural history, marine life, and astronomy.
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.
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.
A bustling entertainment hub featuring a 15-story Ferris wheel, theaters, restaurants, and seasonal events, drawing approximately 8 million visitors annually
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.
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.
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
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.
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.
It is a private experience: only your party takes part. Your own group can be up to 15 people on one booking; no other travellers join.
Infants and small children can ride in a pram or stroller Specialized infant seats are available
Yes, bookings are confirmed instantly.
Travellers rate it 4.6 out of 5 across 38 reviews on Viator and Tripadvisor; it is run by Cavani Tours.
