Duration
8 to 9 Days
Type
Private
Language
Cancellation
Please refer to the 'Additional Info & FAQ' Section below

Your Unforgettable Urban Escapade

Discover the riveting blend of architectural marvels, cultural richness, and gastronomic delights with our Tale of Two Cities Travel Package. Experience the pulsating vibes of New York City and Chicago, two of America's iconic cities, while wrapped in the comfort of our premium offerings and dedicated service.

Your Stay in the Heart of Urban Grandeur

Begin your urban odyssey with a 4-night stay in NYC's upscale hotel, your haven amidst the city's exhilarating pace. The next leg of your journey takes you to Chicago for a 3-night stay, where architectural wonders meet Midwestern charm.

At the heart of your experience is the luxury and comfort of premium accommodations. Nestled in the heart of the cities, these hotels provide a tranquil retreat from the urban buzz. Combined with our premium transportation services available in both cities ensure your journey remains hassle-free from the get-go.

The Exclusive Tale of Two City Package™ includes:

  • Accommodation in NYC (4-Star or 5-Star Hotel)
  • Round-trip Private Airport Transfers in NYC
  • Two Bespoke Experiences in NYC (i.e.: walking tour)
  • Accommodation in NYC (4-Star or 5-Star Hotel)
  • Round-trip Private Airport Transfers in Chicago
  • Accommodation in CHI (4-Star or 5-Star Hotel)
  • Round-trip Private Airport Transfers in NYC
  • One Private City Tour in Chicago
  • One River Cruise in Chicago

Our package unfolds the cities' narratives through meticulously designed private tours. In NYC, you will uncover the secrets of Brooklyn, soak up panoramic views from one of the many rooftop terraces, and marvel at the dazzling lights of the city skyline from the other side of the Hudson River while visiting the charming town of Hoboken. When in Chicago, you will explore its magnificent skyline, relish the beauty of Navy Pier, or delve into the city's vibrant art scene. Each tour is a unique experience, bringing you closer to the city's heartbeat.

HIGHLIGHTS

Hotel + Round-trip Airport Transfer in NYC & Chicago
2 Private Walking Tours with your Tour Guide in NYC
Private City Tour of Chicago
Architecture River Cruise in Chicago
Access to our Concierge Team for Add-on and Special Services
OPTIONAL: include your air fare ticket

Book your spot now

Book your spot now
Select a date to book your experience

Delve into NYC & Chicago's Allure - Dedicated Planning

We believe in crafting experiences as diverse and distinctive as our clients. Beyond the sightseeing, we ensure your travel story incorporates your preferences. Whether it's sampling NYC's foodie hotspots or catching a jazz show in Chicago, we create an itinerary that truly resonates with you.

Our Tale of Two Cities Travel Package is not merely a trip; it's an exploration of urban diversity through a luxury lens. From NYC's high-end shopping and Broadway shows to Chicago's legendary deep-dish pizza and boat tours, we curate a journey that surpasses borders and expectations.

Aside from lodging in both cities, your Tale of Two Cities Travel Package will include the following experiences:

_ Private AM Walking Tour (4-hour) in NYC tailormade itinerary to visit some of the most iconic corners and hidden gems of the Big Apple.

_ Private PM Walking Tour (4-hour) in NYC crafted around the incredible city skyline and the dazzling views from the other side of the Hudson River.

_ Private City Tour (3.5-hour) in Chicago to explore the windy city with your personal tour guide.

_ Architecture River Cruise in Chicago for some of the most unique views over the cityscape

_ Round-trip Airport Transfers in both cities, so you don't have to stress at your arrival in New York City and Chicago, or when leaving for the airport.

Recommended Length of your stay: 7 nights/8 days

Hotel in NYC & Chicago: One of our handpicked hotels - option to choose between 4 and 5 stars hotels.


AVAILABLE YEAR-ROUND


For those seeking to upgrade their NYC experience, and add more activities during their stay, we highly recommend the following.

  • Elegant Cruise along the Hudson River
  • Broadway Show (VIP Tickets available)
  • Helicopter Tour (regular or private options available)
  • Bespoke Day Trips Outside NYC
  • Chauffeured Vehicle Tour — add a TLC car during one or both of our walking tours - starting at $416.00
  • ONE Vanderbilt - SUMMIT ONE Admission or similar attractions

Inclusions

    • Hotel - room only
    • Airport Transfers
    • AM Private Walking Tour in NYC - 4-hour
    • PM Private Walking Tour in NYC - 4-hour
    • Private City Tour in Chicago
    • Architecture Cruise in Chicago

Exclusions

    • Transportation during the tours
    • Admission to Attractions and Museums unless explicitly listed in the inclusions
    • Food and Beverages
    • Gratuity to Tour Guide
    • Gratuity to Driver
    • Any service that is not EXPLICITLY LISTED in the inclusion section

Pricing

TALE OF TWO CITIES TRAVEL PACKAGE

The following rates are starting prices and may change without prior notice due to availability and rate increases especially on weekends and major holidays.

with 7 nights at 4-star Hotel 

$3,017 per person | based on a party of two
$2,060 per person | based on a party of tree


with 7 nights at 5-star Hotel

$4,344 per person | based on a party of two
$2,944 per person | based  on a party of three


OPTIONAL AIR FARE: 

We can add domestic and/or international flights to your package.

AVAILABLE ADD-ON:

  • Private Tour Transportation Add-on - Starting from $416.00 per 4-hour tour
  • SUMMIT ONE Add-on - Starting $48.00 per person
  • Private Helicopter starting from $1,650 or Regular Helicopter starting from $275
  • VIP Broadway Shows from $250
  • Dinner Cruises in Yachts starting from $240
  • Private Tour of Radio City Music Hall - Starting from $910
  • Private Tour of Madison Square Garden - Starting at $910
  • Attraction Pass in NYC and Chicago - Starting at $109

PLEASE NOTE THE INITIAL $75 PLANNING FEE IS REQUIRED TO START THE RESERVATION PROCESS. THE PLANNING FEE CAN BE USED TOWARDS THE PACKAGE OR AN ACTIVITY. THE PLANNING FEE IS NOT REFUNDABLE.

Activity Schedule

Available year-round.

Additional Info & FAQ

CANCELLATION POLICY FOR CUSTOM TRAVEL PACKAGES

For all custom travel packages, the cancellation policy is subject to change depending on the travel components included in the package. The specific cancellation policy will be shared along with your package estimate. 

At a minimum, the following cancellation policy will be in effect:

  • A 10% deposit is due at booking and is not refundable 
  • Up to 15 days from the first date of service - 90% refundable
  • Between 14 days and 7 days - 50% refundable
  • Between 6 days and 0 days - ALL SALES ARE FINAL


TICKETS & FINAL SALE ITEMS:
If your custom travel package includes tickets and other "all sales are final" services, those cannot be rufnded and their amount will be deducted from the refund.

AIRFARE: If airfare is included in your package, we remind you that airfare is completely non-refundable and non-changeable.

You can read our full Cancellation Policy by clicking here


PLEASE NOTE THE INITIAL $75 PLANNING FEE IS REQUIRED TO START THE RESERVATION PROCESS. THE PLANNING FEE CAN BE USED TOWARDS THE PACKAGE 10% DEPOSIT OR AN ACTIVITY. THE PLANNING FEE IS NOT REFUNDABLE.


Tour Company meets luxury dmc in New York City
Tailored Journeys
Trusted Bookings
Top-Rated Escapes
Your vacation, your way!
Flexible Travel
COMPLIMENTARY CANCELLATION OPTIONS

Embrace the freedom of stress-free planning. With our flexible cancellation policy, you can adapt as your plans evolve. Enjoy the liberty to change with most of our services and tours.

*Exclusions apply, see individual tours for details.*
be free!
Testimonials & Reviews
"Excellent firms don’t believe in excellence – only in constant improvement and constant change." – TOM PETERS
4.9
Based on 250 reviews
What They
Say
Breanna A. | TripAdvisor
5-Star Review on TripAdvisor
Irene was a FANTASTIC tour guide! She was so knowledgeable about the area and was so patient with all our questions. We stopped to use the bathroom and we got coffee halfway through, she was so kind! It was a pleasure learning about Brooklyn from you!

From TripAdvisor - April 2022
Giuseppe M. | Google
5-Star Review on TripAdvisor
Excellent guide, excellent organisation, Irene always ready to respond, available in every topic with competence, you can feel the passion for her work. Her voice accompanied our tour, we will miss you!

From Google - January 2024
Carmine S. | Google
5-Star Review on TripAdvisor
An extraordinary experience: I had the pleasure of having Irene as my guide for two days and thanks to the passion she puts into guiding you through the streets of NYC, the anecdotes, the trivia she lets you discover, and the facets she shows during the tour you can't help but fall even more in love with this wonderful city.

From Google - February 2024
Erica F. | Google
5-Star Review on TripAdvisor
[...] unique, very professional, courteous, friendly we can only write positive adjectives, you made us feel at home and have the desire to return. Super recommended. Erica, Marco, Annalisa and Giuseppe.

From Google - December 2023
DCA1014 | TripAdvisor
5-Star Review on TripAdvisor
I’m the biggest fan of Fall activities, but haven’t had a chance to do anything beyond Apple Picking in NJ. I decided to take a last minute 2 day trip with a friend in Hudson Valley, but didn’t know where to start [...] Thankfully I was able to use New York Welcome to do the hard work for us [...]

From TripAdvisor - October 2021
Keena B. | TripAdvisor
5-Star Review on TripAdvisor
The SATC walking tour is fabulous! Our tour guide was amazing. Friendly, helpful, accommodating and so knowledgeable about the city. It was essentially 2 tours in 1. SATC and visits to historical places in the city. I give this tour 5 stars and definitely recommend. Grab your walking shoes and schedule one today!

From TripAdvisor - August 2021
Amber M. | Google
5-Star Review on TripAdvisor
Our family had a wonderful experience seeing Ellis Island and Liberty Island! Irene was very knowledgeable and engaging for our three children ages 5, 9, and 12. We will definitely book again with her [...]

From Google - November 2022
Giorgia M. | Google
5-Star Review on TripAdvisor
We did 2 tours together with our guide Irene in one day, Hoboken and the East side. What can I say, in addition to the wonderful places, she has made everything more magical [...]

From Google - January 2023
We are social Join our community of over 350K Followers!
Office
Manhattan - NYC
New York, NY 10029
Ph: +1 (646) 596-9011
info@newyorkwelcome.net
MY CART
Loading...
CHECK-OUT
Loading...
PAYMENT
Secure Checkout in a few steps
Item cart added