Private Chicago Guided Tour with Hotel Pickup and Expert Guides
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Discover Chicago like never before with a private guided tour tailored just for you. Your driver and personal tour guide will take you around the city's most iconic sights, giving you the flexibility to stop whenever you want for photos or to explore on foot.
This 4-hour experience includes hotel pickup from your preferred location within downtown Chicago, making it easy to start your adventure without any hassle. Whether you're interested in famous landmarks or hidden gems, this private tour offers a personalized way to see the Windy City.
Highlights include stops at Daley Plaza, the Lakefront Trail, Grant Park, Cloud Gate, Navy Pier, and more. After exploring the city's top spots, your tour concludes with a drop-off at your hotel, leaving you with lasting memories of Chicago.
Frequently asked questions
What is included in the private Chicago guided tour?
The tour includes a private vehicle with driver, a dedicated official tour guide, hotel pickup and drop-off within Chicago, and all taxes.
How long is the tour?
The tour lasts approximately 4 hours, giving you plenty of time to see major sights and take photos.
Can I customize the stops?
Since it's a private tour, you can request to spend more time at certain locations or explore specific areas on foot.
Are entrance tickets included?
No, entrance tickets are not included. You’ll have the chance to view many sites from outside, but some attractions may require separate admission.
Is the tour suitable for children or infants?
Yes, infants and small children can ride in a pram or stroller. The tour is suitable for all physical fitness levels.
How do I arrange pickup?
Pickup is available from over 105 hotels in Chicago. The exact pickup time will be confirmed after booking.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 4 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Taxes
- Private vehicle with driver for 4 hours
- Hotel pickup and drop-off within Chicago
- Private official tour guide for 4 hours
Not included
- Gratuities
- Entrance tickets
Itinerary
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Stop 1
View at the Loop’s Daley Plaza. Take in The Picasso sculpture and enjoy a quick look at the square.
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Stop 2
The Lakeside Trail stretches 19 miles from Lake Michigan to the South Shore Cultural Center and Kathy Osterman Beach.
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Stop 3
East Adams Street off South Michigan Avenue. Photo opportunity at the Historic Route 66 Sign.
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Stop 4
Grant Park, a 319-acre green space bordered by Lake Michigan, perfect for photos and relaxing.
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Stop 5
Visit Cloud Gate, the iconic sculpture also known as 'The Bean'. Walk around, take photos, and enjoy the view.
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Stop 6
Explore the downtown area and the Loop Retail Historic District, with opportunities for photos and walking.
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Stop 7
Walk along Riverside Walk for additional photos and sightseeing.
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Stop 8
Outside view only. Entrance tickets are not included and cannot be purchased on the day of the tour.
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Stop 9
Navy Pier, a 3,300-foot-long pier on Lake Michigan, located in Streeterville.
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Stop 10
Photo stop at Buckingham Fountain in Grant Park, one of Chicago’s most famous landmarks.
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Stop 11
Enjoy a comprehensive 4-hour guided tour with your driver-guide, discovering Chicago’s highlights.
Meeting point & pickup
Pickup available, or meet at the start point
How to get there
Pickup is available from 105 listed hotels. Exact pickup time will be confirmed after booking.
Cancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day before
- 0% refund if cancelled within 24 hours
Instant confirmation
Your booking is confirmed immediately after checkout.
From $785.27 per person
- Free cancellation
- Secure checkout with our booking partner
