You booked this experience
Make your trip unforgettable

Private Holiday City Tour

3 Reviews 5.00 out of 5 stars Based on 3 reviews collected by Key West Private Charters and TripAdvisor | Recommended by 100% of reviewers | Chicago, USA
Don't miss out!
On average, this is booked 15 (0) days in advance.

3 hours (approx.)
Hotel pickup offered
Mobile ticket
Offered in: English
Instant confirmation

Overview

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal guide! Enjoy all the Holiday sites the city is known for including, Daley Plaza's Christkindl Market, Macy's Walnut Room and animated story windows, the Goodman Theatre, and marvel at the skaters under the iconic "Bean" of Millennium Park. This experience is the only way to see Chicago during the holidays!

What's Included

  • Private transportation
  • Licensed and certified guide
  • Tea and coffee Coffee and/or Tea
See 1 more

Meeting and Pickup

Pickup point
Pickup details

Your guide and driver will pick you up at your downtown Chicago location.

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.
Read more

Safe & secure Easy breezy Hassle‑free

Magnificent Mile

This is where Chicago really shines with multiple holiday displays!
Read more

30 minutes Admission Ticket Free

Downtown / The Loop

Enjoy the breathtaking views of Chicago during the holidays in this private experience! Your personal guide and driver will show you what makes this city so spectacular during the holidays! Stops include Daley Plaza's Christkindl Market, Macy's Walnut Room and animated story windows, the Goodman Theatre, and marvel at the skaters under the iconic "Bean" of Millennium Park!
Read more

1 hour Admission Ticket Free

Solidarity Drive

Best view of the city’s skyline as we enjoy Chicago’s Musuem campus!
Read more

30 minutes Admission Ticket Free

Lincoln Park

Lincoln Park is beautiful during the holiday especially with the zoo lights!
Read more

30 minutes Admission Ticket Free

Show 3 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

Frequently Asked Questions (7)

Q: What is the cancellation policy for the Private Holiday City Tour?

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-106682P3

Traveler Photos

Reviews

5.00
3 reviews

Average 5.00 out of 5 stars based on 3 traveler reviews collected by Key West Private Charters and partner sites such as Cool Destinations and TripAdvisor

5 stars
3
4 stars
0
3 stars
0
2 stars
0
1 star
0
Don't miss out!
On average, this is booked 15 (0) days in advance.

Similar Tours & Activities

Chicago Highlights Running Tour

Join us for the most memorable experience you will have while visiting Chicago! For runners from around the world, this is definitely a “bucket list” …More

Likely to Sell Out
Likely to Sell Out

Join us for the most memorable experience you will have while visiting Chicago! For runners from around the world, this is definitely a “bucket list”...

1 hour 15 minutes Free Cancellation
from
$44

Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your …More

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your...

3 to 4 hours Hotel pickup offered Free Cancellation
5.0 (203)
from
$539

Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables, …More

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables,...

2 hours
4.8 (4)
from
$87

Chicago Hauntings Original Ghost Bus Tour

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by …More

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by...

3 hours Free Cancellation
4.1 (136)
from
$59

Travelers Who Bought This Tour Also Bought

Chicago River 90 Minute Architecture Tour

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to …More

Likely to Sell Out
Likely to Sell Out

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to...

1 hour 30 minutes Free Cancellation
4.8 (11,096)
from
$45

Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years …More

Likely to Sell Out
Likely to Sell Out

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years...

1 hour 30 minutes Free Cancellation
4.8 (2,424)
from
$45

Chicago Crime and Mob Bus Tour

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities. …More

Likely to Sell Out
Likely to Sell Out
4.6 (3,568)

Chicago Crime and Mob Bus Tour

4.6 (3,568)

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities....

90 to 120 minutes Free Cancellation
4.6 (3,568)
from
$49

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich …More

Likely to Sell Out
Likely to Sell Out

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich...

45 minutes Free Cancellation
4.8 (3,587)
from
$28

What's Included

Activity name

  • Private transportation
  • Licensed and certified guide
  • Tea and coffeeCoffee and/or Tea

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

Report Product Issue

Activity name