City Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top City Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,719, price is now CA $1,536 per person
CA $1,536
per person
Jun 28 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Don’t ever think you will check in prior to the late 4pm check in. No matter what. Not even 5 minutes.

Reviewed on Apr 17, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was CA $7,190, price is now CA $4,007 per person
CA $4,007
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on Mar 19, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $3,158, price is now CA $1,803 per person
CA $1,803
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,951 reviews)
The staff was extremely helpful in answering any questions we had and providing recommendations for restaurants and directions. The rooms and property were always clean. Breakfast provided many choices da and was always well stocked. The breakfast bone moves quickly and efficiently. The frosted glass shower/bathroom wall” was NOT an issue as the person in the bathroom could only be seen as a “blob.”

Reviewed on Apr 14, 2026

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $3,209, price is now CA $1,889 per person
CA $1,889
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (205 reviews)
I did not have breakfast, but I heard the breakfast. There is amazing. The bar was awesome. Great selection.!

Reviewed on Apr 4, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $5,449, price is now CA $3,212 per person
CA $3,212
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,006 reviews)
Everything is great about this Hotel.

Reviewed on Apr 9, 2026

Ready to book your vacation to City Island?

 

Choose your dates

City Island Hotel Deals

Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
109 East 42nd Street New York NY
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from Apr 26 to Apr 27
CA $240
CA $343 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (6,679 reviews)
All good

Reviewed on Apr 17, 2026

Hyatt Grand Central New York
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 CA $141 per night from Apr 19 to Apr 20
CA $141
CA $230 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (5,396 reviews)
Noisy neighbourhood Bad listeners- they charged my stay on the wrong credit card despite me warning them They charge for keeping your luggage in the locker room. Other hotels don’t

Reviewed on Apr 18, 2026

Hotel Edison Times Square
DoubleTree by Hilton New York Downtown

DoubleTree by Hilton New York Downtown

4 out of 5
8 Stone St New York NY
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Apr 26 to Apr 27
CA $165
CA $195 total
Apr 26 - Apr 27
includes taxes & fees
8.4/10 Very Good! (3,670 reviews)
Clean room, but elevators take too long

Reviewed on Apr 17, 2026

DoubleTree by Hilton New York Downtown
See all 12,244 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in City Island

Times Square

Times Square

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

Times Square
Central Park

Central Park

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

Central Park
view from top on Madison Square Garden and Empire State Building. Night Lights

Madison Square Garden

Whether you’re performing here, watching your favorite sports team or entertainer or touring the venue, you’re in for an exciting event.

Madison Square Garden

What to do in City Island

SUMMIT One Vanderbilt Experience Tickets

SUMMIT One Vanderbilt Experience Tickets

CA $66
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

CA $50
per traveller
90% of travellers recommend
Madame Tussauds New York Celebrity Wax Museum
Go City: New York Explorer Pass - Entry to 2 to 10 Top Attractions

New York Explorer Pass: Visit 2-10 Attractions and Save Up to 50 Percent

CA $122
per adult
84% of travellers recommend
New York Explorer Pass: Visit 2-10 Attractions and Save Up to 50 Percent
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.

Explore a world of travel with Expedia

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