Chicago City Private Tours
Pick your date
Highlighted days have spots open. Grey days are sold out or not running.
September 2026
Loading live availability
Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.6/5
Based on 38 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Chicago City Private Tours worth booking?
Chicago City Private Tours is a 2-hour experience in Chicago, United States, from $199 per person. It scores 56 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 4.6/5 rating across 38 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 56 / 100
- Rating
- 4.6/5 (38)
- Duration
- 2 hours
- From
- $199 per person
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 s
What you get
About this experience
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
Included
- Private transportation
- Bottled water
- Snacks
- In-vehicle air conditioning
- Surcharges on fuel
- Parking fees
Not included
- Gratuities
What you'll see and do
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.
10 minutes here
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
45 minutes here · Admission not included
The Magnificent Mile
A premier shopping district along Michigan Avenue, lined with luxury boutiques, historic landmarks, and renowned eateries.
1 minutes here
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.
20 minutes here
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.
15 minutes here
The Chicago Theatre
An iconic venue hosting concerts, plays, and special events in a historic setting.
1 minutes here
Chicago Cultural Center
A stunning architectural gem hosting free art exhibitions, performances, and public events.
10 minutes here
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.
25 minutes here
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.
1 minutes here
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.
1 minutes here
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
10 minutes here
The Rookery Building
The Rookery Building remains a cherished piece of Chicago's architectural heritage, reflecting the city's innovative spirit and historical depth.
1 minutes here
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.
5 minutes here
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.
15 minutes here
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.
45 minutes here · Admission not included
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.
10 minutes here
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.
15 minutes here
Jackson Park's Japanese Garden
A historic park on the South Side, home to the Museum of Science and Industry and beautiful lagoons.
1 minutes here
Obama Presidential Library
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.
Pass by without stopping
Frank Lloyd Wright Trust - Frederick C. Robie House Tour
A Frank Lloyd Wright masterpiece located in Hyde Park, exemplifying Prairie School architecture.
1 minutes here · Admission not included
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.
10 minutes here
Museum Campus
A scenic lakefront area encompassing the Field Museum, Shedd Aquarium, and Adler Planetarium, offering insights into natural history, marine life, and astronomy.
1 minutes here
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.
40 minutes here · Admission not included
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.
10 minutes here
Navy Pier
A bustling entertainment hub featuring a 15-story Ferris wheel, theaters, restaurants, and seasonal events, drawing approximately 8 million visitors annually
1 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 15 minutes before departure.
Options you can book
Personalized 2-Hour Tour
Duration: 2 hours Personalized 2-Hour Tour: Our 2-hour tour is fully customizable. Choose the specific attractions or experiences you'd like to focus on, and we'll adjus comfortable car Pickup included
Boat Tour Combo
make it a combo: make it a combo by adding a boat tour to your city tour for only 299$ on our 18ft pontoons . Duration: 2 hours 18ft pontoon Pickup included
4-Hour Tour with Free Pictures
Duration: 4 hours choose your Route: With our 4-hour tour, you have the flexibility to choose your route and handpick the stops you'd like to visit from the itine Pickup included
Half day Tour (6H)
Duration: 6 hours Free snacks : enjoy the added perk of free snacks to make your experience even more enjoyable. Half day Tour with Free Pics: Personalize your tour to suit your interests, and take home high-quality photos from your journey comfortable car Pickup included
Day Tour (8H)
40 minute break: Take a 40-minute break to relax and recharge with complimentary coffee and a selection of delightful sweets. Personalized Photo Stops: Select unique and picturesque spots for photo opportunities, ensuring guests can take home beautiful memories. comfy car Duration: 8 hours Free coffee and sweets: As you explore the city in style, enjoy gourmet coffee and delicious sweets at no extra cost. All day Tour with Free Pics: Personalize your day tour by selecting your preferred route and stops from the itinerary. Your adventure, your way ! Pickup included
Luxury Tour (5 Hours)
Luxury Car(BMW,Mercedes,Audi) Pickup included
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- ar, en, fr
- Ticket
- Mobile Only
- Runs on
- Mon, Sat, Sun
- Group size
- Up to 15 travelers per booking
- Operated by
- Cavani Tours
Know before you go
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
Photos
What travelers are saying
Outty’s summary of the themes that recur across 38 traveler reviews. Written by us, not quoted from reviewers.
The guide
8 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
4 mentionsReviewers describe the commentary as informative rather than scripted.
Value for money
3 mentionsTravelers feel they got more than they paid for.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
38 verified traveler reviews for Chicago City Private Tours. Ratings and reviews provided by Viator and Tripadvisor.
Not Worth the Money
This private tour definitely wasn’t worth $199.00, wish I had of saved and took the small group for only $50 since they both was only 2 hours. Be sure to know exactly what you’re booking before paying.
via Viator
Not worth the money.
Not worth the trouble. Extra fee charged after ticket was issued. Your guide tried, but was not very good.
Response from the operator: Thank you for your review. To clarify, the extra fee you were charged was for the SUV upgrade, which you requested and agreed to prior to the tour. We want to be transparent that this was not an unexpected charge – it was communicated and approved by you in advance. We're sorry the guide wasn't up to your standards. We'll address this with our team. Thank you for your feedback.
via Viator
Ilyas was very...
Ilyas was very accommodating and customized the tour to show me what I wanted to see. He dropped me off right at the sights or parked very close and came with me and took a lot of pictures.
via Viator
Very poorly organized!
The tour guide was excellent and despite having lived in the city in the past, we discovered hidden treasures. We have undertaken many private tours through Viator and previously all have been superb. The reason for the low score here is because the local agent charged us an additional $79 for the Tour as they said the original vehicle would be too small. We agreed the day before and we toured in a BMW X3. Trust me, with 4 adults, three of which were over 6’ tall (and the tour agent knew this), it was not very comfortable. I dread to think what the original vehicle was and smacks of a scam. In addition, as we were waiting to be picked up to start the Tour at 9:00am, the Agent emailed and said that the Tour would be starting one hour later as they had to collect the upgraded vehicle. All in all, the organization was very poor with just a sorry! We would try Viator again but would recommend not using them in Chicago as their Agent is very poor.
Response from the operator: Thank you for your feedback, and we sincerely apologize for the inconvenience you experienced. We truly appreciate you taking the time to share your concerns. We're glad to hear that you enjoyed your tour guide and discovered some hidden treasures in Chicago – that means a lot to us. Regarding the vehicle upgrade, we did inform you that the upgraded SUV would be a BMW X3, and we received your confirmation to proceed with it. We understand that space was still tight for your group, and we regret that it didn't meet your comfort expectations. We will take this into consideration for future groups of similar size. As for the delayed pick-up, we completely understand your frustration. Unfortunately, traffic in Chicago can be unpredictable and sometimes causes unavoidable delays beyond our control. We sincerely apologize for any disruption this caused to your schedule. We take your feedback seriously and will work with our local team to improve communication and coordination. We hope you'll give us another chance in the future to provide you with the exceptional experience we strive for. Thank you again for your honest review.
via Viator
A Really Good Day
It was one of the most courteous tour experience. Our guide was knowledgeable of what we desired. Muhammad is a good driver and we felt safe throughout the whole downtown Chicago experience.
Response from the operator: Thank you! So glad Muhammad made you feel safe and gave you exactly what you were looking for. We'll pass this along to him – thanks for touring with us!
via Viator
Good to know
- Duration
- 2 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Mon, Sat, Sun
- Price range
- $199 to $599
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 13
- Verdict
- Worth a Look
Why this scores 56
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Chicago City Private Tours: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Chicago.
How much does Chicago City Private Tours cost?
+
Prices start at $199 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Chicago usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Chicago City Private Tours take?
+
Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Chicago is not rushed.
Is Chicago City Private Tours worth it?
+
It holds an Outty Ranking of 56 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.6/5 across 38 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Chicago, and how flexible the cancellation terms are.
Can I cancel or reschedule Chicago City Private Tours?
+
Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Chicago City Private Tours suitable for kids and families?
+
Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Chicago City Private Tours?
+
Around 13 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Chicago can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
+
Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Chicago and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.
Where does Chicago City Private Tours start and how do I get there?
+
The exact meeting point and directions are on your voucher once you book, and they sit in central Chicago within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Chicago?
+
Chicago's signature experience is still the architecture boat cruise, and the difference between the docent-led originals and the party-boat imitators is the single biggest quality gap in the city. Beyond the river: gangster history walks, Art Institute access, deep-dish and hot-dog crawls, and skydeck timed entry. Outty Ranking leans on guide credentials and how consistently the promised route runs. On Outty we rank every Chicago experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Original Chicago Architecture Interiors Tour: Dazzling Interiors, Chicago Murder Mystery Tour, Chicago Favorites Ultimate Food and Walking Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Chicago?
+
May to October. Winter cruises stop running when the river ices. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Chicago?
+
Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
+
Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
Ready to lock in your spot?
Pick a date, choose your group, and see the exact price for Chicago City Private Tours.
Pick your date
