City Island Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in City Island

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Save 100% on your flight
Price was €1,055, price is now €679 per person
€679
per person
12 Nov - 16 Nov
found 16 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
7/10 Good! (2,403 reviews)
The area is great, but the hotel itself is quite old and outdated. If you’re on a tight budget and need a place to stay, it’ll suffice, but don’t expect anything fancy.

Reviewed on 3 Oct 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was €2,174, price is now €1,260 per person
€1,260
per person
13 Nov - 16 Nov
found 2 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Every staff person I interacted with was friendly and helpful. Loved the views and location. Wished there was more room to walk in the living room when the pull out sofa was open.

Reviewed on 28 Sept 2025

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Save 100% on your flight
Price was €2,748, price is now €1,710 per person
€1,710
per person
13 Nov - 16 Nov
found 2 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (576 reviews)
Beautiful rooms, great restaurant and bar with a view of central park

Reviewed on 1 Oct 2025

Pendry Manhattan West

Pendry Manhattan West

5 out of 5
Manhattan
Save 100% on your flight
Price was €2,181, price is now €1,372 per person
€1,372
per person
13 Nov - 16 Nov
found 2 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.8/10 Exceptional! (447 reviews)
Beautiful hotel with great views of the city. Wonderful staff. Zou Zous restaurant in the hotel is really good. We stayed in the deluxe king and there was ample drawer space to unpack. There are 2 Starbucks steps from the hotel and many outdoor seating areas around the hotel. The 7 train is 1 short block away, and Hudson Yards is across the street. We loved it!

Reviewed on 1 Sept 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was €2,337, price is now €1,494 per person
€1,494
per person
13 Nov - 16 Nov
found 2 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (138 reviews)
A perfect place to stay!!

Reviewed on 20 Sept 2025

Top hotels in City Island

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 €230 per night from 19 Oct to 20 Oct
€230
19 Oct - 20 Oct
includes taxes & fees
7.2/10 Good! (4,861 reviews)
"Its near times square"

Reviewed on 29 Sept 2025

Sheraton New York Times Square Hotel
Hotel Edison Times Square

Hotel Edison Times Square

4 out of 5
228 W 47th St, New York, NY
Fully refundableReserve now, pay when you stay
The price is €216 per night from 5 Oct to 6 Oct
€216
5 Oct - 6 Oct
includes taxes & fees
8.2/10 Very Good! (4,681 reviews)
"It was a great experience. Very convenient. What we didn't like waa no fridges in the room. Otherwise every place is accessible for a night out on the town."

Reviewed on 30 Sept 2025

Hotel Edison Times Square
Paramount Times Square – A Generator Hotel

Paramount Times Square – A Generator Hotel

4 out of 5
235 West 46th Street, New York, NY
Fully refundableReserve now, pay when you stay
The price is €174 per night from 5 Oct to 6 Oct
€174
5 Oct - 6 Oct
includes taxes & fees
7.6/10 Good! (1,260 reviews)
"Great location, Friendly staff, clean room comfy bed room and bathroom was updated"

Reviewed on 1 Oct 2025

Paramount Times Square – A Generator Hotel
See all 10,710 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.

Popular places to visit

Times Square

Times Square

4/5(1,706 reviews)

Visit this iconic square with its dazzling surroundings and vibrant mix of people, and see what makes New York tick.

Times Square
Central Park showing a garden, flowers and a pond

Central Park

4.5/5(1,405 reviews)

Visit this green oasis in central Manhattan to chill out and escape from the stresses and strains of urban life.

Central Park
Ed Sullivan Theater which includes signage and a city as well as a large group of people

Broadway

4.5/5(1,388 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

What to do in City Island

Edge New York City

NYC Edge Observation Deck at Hudson Yards Admission Ticket

€33
per adult
84% of travellers recommend
NYC Edge Observation Deck at Hudson Yards Admission Ticket
Statue of Liberty & Ellis Island Tour + Pedestal Access

Statue of Liberty & Ellis Island Tour: All Options

€53
per adult
94% of travellers recommend
Statue of Liberty & Ellis Island Tour: All Options
New York's Hidden Gems: Self-Guided City Tour

New York's Hidden Gems: Self-Guided City Tour

€3
per adult
New York's Hidden Gems: Self-Guided City Tour
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 travellers 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 holiday 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.