City Island Vacation Packages

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Top City Island Vacation Deals

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

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,308, price is now CA $830 per person
CA $830
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (3,144 reviews)
The location is amazing. Near to the subway for a quick ride to Times Square. But everything you need in walking distance. Near to la guardia airport. Rooms are small but comfortable and have everything you need. I would stay here again.

Reviewed on Jun 20, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,957, price is now CA $2,288 per person
CA $2,288
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
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 $3,131, price is now CA $2,049 per person
CA $2,049
per person
Aug 25 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
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

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $1,734, price is now CA $1,189 per person
CA $1,189
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,003 reviews)
We usually stay at the Ritz but prices were up overall due to the World Cup so we tried this property. It was fantastic and we may have found a new favorite.

Reviewed on Jun 15, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,301, price is now CA $894 per person
CA $894
per person
Jul 31 - Aug 3
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,435 reviews)
Perfect location for a great price. Small older hotel but rooms and bathroom were very clean. It sits next to a really fun pub.

Reviewed on Jun 20, 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 $310 per night from Jun 21 to Jun 22
CA $310
CA $426 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (7,172 reviews)
"The hotel staff were very nice. The only issue I had was they had one valet driver that serviced 3 properties. They said it would take 30-60 minutes for us to get our car. The staff claims it’s because of the hour we checked out which was 6am. That’s still seems unreasonable, given the fact it was ..."

Reviewed on Jun 20, 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 $324 per night from Jul 1 to Jul 2
CA $324
CA $434 total
Jul 1 - Jul 2
includes taxes & fees
7.4/10 Good! (8,302 reviews)
"The room was dated and had damage and mold. The elevator situation was miserable. We had to wait a lot, have traveled a lot and stayed in a variety of places and this was the only hotel Iv seen do elevators this way. Needs updating"

Reviewed on Jun 20, 2026

Sheraton New York Times Square Hotel
Pod Times Square

Pod Times Square

3 out of 5
400 W 42nd Street New York NY
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Jul 2 to Jul 3
CA $168
CA $230 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (5,684 reviews)
"Clean. Some staff amazing, some staff could do with a rocket up.their arse to actually do their job!"

Reviewed on Jun 20, 2026

Pod Times Square
See all 12,127 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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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
A cityscape with prominent skyscrapers, including the Empire State Building, and a large circular building with illuminated pink and purple 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
94% of travellers recommend
SUMMIT One Vanderbilt Experience Tickets
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
Stranger Things: The First Shadow on Broadway

Stranger Things: The First Shadow on Broadway

CA $127
per adult
Stranger Things: The First Shadow on Broadway
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.