City Island Vacations from ￥214,625

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest City Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The William Vale

The William Vale

5 out of 5
Price was ￥320,990, price is now ￥214,625 per person
￥214,625
per person
Feb 6 - Feb 11
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (NYC)
17.6/10 Exceptional! (1,002 reviews)
The 2 concierges Samantha & Daniella -were fabulous! So appreciative!

Reviewed on Nov 22, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥563,092, price is now ￥344,590 per person
￥344,590
per person
Feb 6 - Feb 11
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (NYC)
19.2/10 Exceptional! (159 reviews)
What an incredibly beautiful place this hotel is! Staff cannot do enough and made ourspecial anniversary stay truly perfect..the hotel is beautifully decorated and immaculate throughout. Cannot recommend this enough

Reviewed on Nov 17, 2025

Faena New York

Faena New York

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥732,992, price is now ￥462,774 per person
￥462,774
per person
Feb 3 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
No reviews
Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was ￥383,337, price is now ￥248,267 per person
￥248,267
per person
Dec 30 - Jan 5
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newark Liberty Intl. Airport (EWR)
16.8/10 Exceptional! (1,565 reviews)
Good Hotel for business travelers & tourists for Manhattan, NYC region without cars.

Reviewed on Nov 20, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥480,108, price is now ￥320,384 per person
￥320,384
per person
Feb 6 - Feb 11
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (NYC)
18/10 Exceptional! (1,001 reviews)
Loved all the plants in this place and around it. Super chill vibe. Very clean. Front desk staff very kind and helpful!

Reviewed on Nov 23, 2025

Find the Best City Island Vacation Packages

City Island Hotel Deals

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
811 7th Ave New York NY
Fully refundableReserve now, pay when you stay
The price is ￥28,095 per night from Nov 30 to Dec 1
￥28,095
￥39,090 total
Nov 30 - Dec 1
includes taxes & fees
7.4/10 Good! (5,583 reviews)
The room was very clean, and the hotel is located in a great location for walking to the theater, restaurants, and even Penn Station. HOWEVER, the elevator system is horrendous!! Large groups gather in front of the elevator that has been designated to take you to your floor, so we often had to wait ...

Reviewed on Nov 24, 2025

Sheraton New York Times Square Hotel
Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
109 East 42nd Street New York NY
The price is ￥34,910 per night from Nov 29 to Nov 30
￥34,910
￥47,785 total
Nov 29 - Nov 30
includes taxes & fees
8/10 Very Good! (6,360 reviews)
Very

Reviewed on Nov 24, 2025

Hyatt Grand Central New York
Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
145 W 44th St New York NY
Fully refundableReserve now, pay when you stay
The price is ￥21,177 per night from Nov 30 to Dec 1
￥21,177
￥30,252 total
Nov 30 - Dec 1
includes taxes & fees
7.6/10 Good! (6,115 reviews)
Great staff Danny was great

Reviewed on Nov 24, 2025

Millennium Hotel Broadway Times Square
See all 11,057 properties in City Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in City Island

Times Square featuring a city, central business district and signage

Times Square

4.5/5(22,891 reviews)

New York’s infamous neon wonderland is hustle and bustle at its best, and an essential stop for all tourists.

Times Square
Ed Sullivan Theater which includes a city and signage as well as a large group of people

Broadway

4.5/5(15,833 reviews)

Visit the dazzling theater district of one of the world’s most exciting cities. Enjoy the shopping, dining and street entertainment as well.

Broadway
Serenity of Central Park in New York showcases lush greenery and tranquil waters on a beautiful day

Central Park

4.5/5(16,923 reviews)

Offering blissful respite from Manhattan’s concrete jungle, this is the perfect spot to rest weary feet or enjoy a picnic.

Central Park

What to do in City Island

SUMMIT One Vanderbilt Experience Tickets

SUMMIT One Vanderbilt Experience Tickets

￥7,314
per adult
92% of travellers recommend
SUMMIT One Vanderbilt Experience Tickets
Madame Tussauds New York Celebrity Wax Museum

Madame Tussauds New York Celebrity Wax Museum

￥5,733
per traveler
88% of travellers recommend
Madame Tussauds New York Celebrity Wax Museum
One World Observatory: Skip-the-Line Ticket

One World Observatory Tickets

￥4,679
per adult
90% of travellers recommend
One World Observatory Tickets
See all activities in City Island

Frequently asked questions

Can I cancel my flight booking to City Island due to COVID-19?
If you haven't booked yet, read the terms and conditions of your preferred airline. If you've already reserved your flight to City Island, head to our Customer Service Portal. It will help determine which COVID-19 policies are applicable to your reservation and provide you with the next steps.
What's the best way to find cheap flights to City Island that have flexible change policies?
Search for your affordable airfares to City Island, then mark the "No change fee" box directly under the "Flexible change policies" heading. It's that simple. We know that plans change and flexibility matters, so book with confidence with Expedia.
What are some of the general tips for travelers to City Island during the COVID-19 outbreak?
With new restrictions and safety precautions to follow, travel looks a little different at present. Here's what you should know before you pack your bags for City Island:
  • Research if any travel restrictions apply to your origin and destination before locking in your flight. Also check if there are any requirements you'll have to follow on arrival, such as undergoing health assessments.
  • Wear a face mask even during airport screening. A TSA employee will require you to temporarily lower your mask for ID purposes.
  • To reduce the risk of cross-contamination, position your boarding pass on the scanner yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA agent.
  • TSA now allows passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on baggage. This will need to be removed from your bag for X-ray screening.
  • To reduce handling during screening, put items such as your phone, keys and wallet into your carry-on rather than into the bins.
  • Transport your food items in a clear plastic bag and also place them in a screening bin. Keeping your food separate from your carry-on makes it less likely that a TSA employee will need to open your bag for inspection.

Which airlines fly to City Island?
Delta runs flights into or near City Island, including 4895 that travel to John F. Kennedy Intl. Airport (JFK) each month. Choose your travel dates and then secure your fare early to bag a bargain.
How can I find cheap tickets to City Island?
Book well ahead, consider nearby airports, use miles or points — there are loads of ways! One more is to use Expedia's "flexible dates" function. Find your City Island flight, then compare the cheapest prices for nearby dates. In the last seven days, the lowest price for a flight to City Island was .
How much is a flight to City Island?
In the last seven days, return tickets to City Island sold for as little as and reached a maximum of . For one-way trips taking off from (), the lowest price during this time was just .
What are the most popular airports to fly into in City Island?
City Island's main entryway is John F. Kennedy Intl. Airport (JFK). Get your next exciting journey underway by securing a seat on one of the 13452 monthly flights to this destination.
When is the cheapest time to fly to City Island?
If you'd rather spend your vacation cash enjoying the delights of City Island rather than on your journey there, depart early in the week. The cheapest day to travel is generally Tuesday, with Monday coming in second. With many people keeping their travel to weekends, Saturday tends to have the costliest airfares.
How much is a plane ticket to City Island?
Airfares ranged anywhere from to over the last seven days. When you're ready to book, we'll be ready to help you find an awesome deal to City Island.
Which airlines with flights to City Island employ COVID-19 cleanliness policies?
In an effort to reduce contact between passengers and flight attendants during the current pandemic, airlines have taken social distancing and other protective measures to the skies. Just some of these are:
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.