City Island Vacation Packages

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Top City Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,591, price is now CA $1,077 per person
CA $1,077
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
Good location for the price !

Reviewed on Jun 28, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,180, price is now CA $2,473 per person
CA $2,473
per person
Jul 30 - Aug 2
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.

Reviewed on Jun 6, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $2,936, price is now CA $1,849 per person
CA $1,849
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (680 reviews)
A clean professional hotel. The down side is that it is very expensive and whilst the staff are very professional, they could not be described as warm and friendly. But maybe that could be said for New York service generally. Thank you ~ Jon

Reviewed on Jun 20, 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,890, price is now CA $1,217 per person
CA $1,217
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,518 reviews)
The hotel was great. The room was a bit small, but no complaints otherwise.

Reviewed on Jun 25, 2026

Pendry Natirar

Pendry Natirar

5 out of 5
Price was CA $3,728, price is now CA $2,537 per person
CA $2,537
per person
Aug 13 - Aug 16
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
10/10 Exceptional! (12 reviews)
Great rooms, wonderful service and staff, perfect location and very pet friendly.

Reviewed on Apr 26, 2026

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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 $280 per night from Jul 12 to Jul 13
CA $280
CA $391 total
Jul 12 - Jul 13
includes taxes & fees
8.4/10 Very good! (7,258 reviews)
"Hotel is runned down.. there’s nothing GRAND about this hote"

Reviewed on Jun 28, 2026

Hyatt Grand Central New York
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 CA $248 per night from Jul 5 to Jul 6
CA $248
CA $346 total
Jul 5 - Jul 6
includes taxes & fees
7.4/10 Good! (8,406 reviews)
"Room was clean, just a bit on the older looking- very rustic but nice room. We were upgraded to the 39th floor. Housekeeping was lovely."

Reviewed on Jun 28, 2026

Sheraton New York Times Square Hotel
NEW YORKER BY LOTTE HOTELS

NEW YORKER BY LOTTE HOTELS

4 out of 5
481 Eighth Ave. New York NY
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Jul 1 to Jul 2
CA $197
CA $297 total
Jul 1 - Jul 2
includes taxes & fees
8.2/10 Very good! (6,922 reviews)
"The hotel is older but the rooms are really nice. Great location right next to the subway. Staff was really nice, great gym, and the tick tock dinner is awesome. Great food!"

Reviewed on Jun 27, 2026

NEW YORKER BY LOTTE HOTELS
See all 12,143 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.
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Stay near popular City Island attractions

City Island Nautical Museum

You can spend an afternoon browsing the exhibits at City Island Nautical Museum during your trip to Bronx. While you're here, you can savor the top-notch restaurants.
See properties

What to do in City Island

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 $117
per adult
84% of travellers recommend
New York Explorer Pass: Visit 2-10 Attractions and Save Up to 50 Percent
Edge Observation Deck at Hudson Yards

Edge Observation Deck at Hudson Yards

CA $57
per adult
98% of travellers recommend
Edge Observation Deck at Hudson Yards
SUMMIT One Vanderbilt Experience Tickets

SUMMIT One Vanderbilt Experience Tickets

CA $66
per adult
94% of travellers recommend
SUMMIT One Vanderbilt Experience 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.

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