Exclusive Private Holiday City Tour in Chicago
Experience Chicago during the festive season like never before with our Private Holiday City Tour. Travel in style and comfort in a private luxury vehicle, accompanied by your own personal guide who will showcase the city’s most enchanting holiday sights.
From the lively Daley Plaza's Christkindl Market to Macy’s Walnut Room with its animated story windows, this tour captures the magic of Chicago’s holiday spirit. Marvel at the skating under Millennium Park’s iconic "Bean" and enjoy the festive decorations at the Goodman Theatre. It’s the perfect way to see Chicago’s holiday glow up close and personal.
This private tour is designed for flexibility and comfort, making it ideal for families, couples, or small groups wanting a personalized holiday experience. Whether you’re a first-time visitor or a local looking to relive the magic, this tour offers a memorable way to celebrate the season.
Join us for an unforgettable 3-hour journey through Chicago’s most festive spots, with plenty of opportunities for photos and holiday cheer along the way.
Frequently asked questions
How long is the Private Holiday City Tour?
The tour lasts approximately 3 hours, giving you plenty of time to enjoy each stop.
What’s included in the tour?
Your experience includes private transportation and a licensed, certified guide to lead the way.
Is the tour suitable for children?
Yes. Infants and small children can ride in a pram or stroller, and the tour is suitable for all physical fitness levels.
Can I customize the stops or itinerary?
This is a private tour, so your guide can tailor the experience to your preferences within the scheduled stops.
What should I wear or bring?
Dress warmly for outdoor stops, especially during winter months. Comfortable shoes are recommended for walking around the sites.
Is hotel pickup included?
Yes, pickup is available from your downtown Chicago hotel, with the exact time confirmed after booking.
Free cancellation
Cancel at least 24 hours before the scheduled departure for a full refund.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 3 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Private transportation
- Licensed and certified guide
Not included
- Coffee and/or tea
Itinerary
A carefully curated route through Chicago’s most festive holiday spots, with stops at iconic locations and scenic views.
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Stop 1
Kick off your tour at a lively holiday display spot showcasing Chicago’s festive spirit.
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Stop 2
Explore Daley Plaza's Christkindl Market, Macy’s Walnut Room with animated windows, the Goodman Theatre, and enjoy skating under Millennium Park’s "Bean".
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Stop 3
Get the best view of Chicago’s skyline while touring the Museum campus area.
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Stop 4
Visit Lincoln Park to see the beautiful holiday lights and the zoo lights display.
Meeting point & pickup
Hotel pickup included for all travelers.
Your guide and driver will pick you up at your downtown Chicago hotel. Pickup is available from 62 designated hotels, with exact times confirmed after booking.
Open in Google MapsHow to get there
Provide your hotel details during booking to arrange pickup.
Cancellation & confirmation
Free cancellation
Cancel at least 24 hours before the scheduled departure for a full refund.
- 100% refund if canceled at least 1 day in advance
- No refund if canceled within 24 hours of departure
Instant confirmation
Your booking is confirmed immediately after checkout.
From $499.00 per person
- Free cancellation
- Secure checkout with our booking partner
