City Island Packages (Flight + Hotel)

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    Save up to ฿4,531 when you book a flight and hotel together*

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Top City Island Flight + Hotel Deals

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

Hotel St. James

2.5 out of 5
Manhattan
Price was ฿38,129, price is now ฿26,657 per person
฿26,657
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,026 reviews)
The St. James was a great way to experience New York; nestled in to the middle of downtown for easy access to many places. The old interior was iconic and fun, especially riding the tiny elevator. The staff was friendly the room was great in every way except not having a fridge or microwave. I would definitely return here!

Reviewed on 21 Mar 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ฿51,604, price is now ฿34,229 per person
฿34,229
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,931 reviews)
Friendliest staff in reception, bellman and coffee shop. Clean hotel. Great location! Noisy from outside traffic so bring earplugs to sleep.

Reviewed on 21 Mar 2026

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was ฿40,847, price is now ฿31,510 per person
฿31,510
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (4,149 reviews)
Honeymoon was perfect as per travelers

Reviewed on 21 Mar 2026

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Price was ฿42,600, price is now ฿33,549 per person
฿33,549
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,038 reviews)
Cleam room, good service and nice area

Reviewed on 20 Mar 2026

Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Manhattan
Price was ฿34,030, price is now ฿27,336 per person
฿27,336
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
7.8/10 Good! (6,615 reviews)
Great Location, clean rooms

Reviewed on 21 Mar 2026

Top hotels in City Island

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 ฿7,006 per night from 19 Apr to 20 Apr
฿7,006
฿9,664 total
19 Apr - 20 Apr
includes taxes & fees
8.2/10 Very Good! (6,545 reviews)
Our room was clean and the janitorial staff was very nice. The toilet leaked in our room when it was flushed and the ice bucket was gross. When we checked in, I asked about breakfast being included. I was told it wasn’t included and she couldn’t even tell me how much it would be to buy the breakfast ...

Reviewed on 22 Mar 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 ฿5,092 per night from 5 Apr to 6 Apr
฿5,092
฿7,279 total
5 Apr - 6 Apr
includes taxes & fees
7.4/10 Good! (7,263 reviews)
The only issue were delays with the elevators. There was a very large convention going on and the elevators did get bogged down at times.

Reviewed on 21 Mar 2026

Sheraton New York Times Square Hotel
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 ฿3,256 per night from 29 Mar to 30 Mar
฿3,256
฿5,361 total
29 Mar - 30 Mar
includes taxes & fees
7.6/10 Good! (2,272 reviews)
For a budget travel adventure the bunk bed room suited us fine. It was a tad older, but the vibe of the hotel was good.

Reviewed on 20 Mar 2026

Paramount Times Square – A Generator Hotel
See all 12,163 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 featuring a city, central business district and signage

Times Square

4/5(1,707 reviews)

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

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

Central Park

4.5/5(1,408 reviews)

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

Central Park
NewYork_MadisonSquareGarden_6291778_8

Madison Square Garden

4.5/5(349 reviews)

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

฿1,487
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

฿1,141
per traveller
90% of travellers recommend
Madame Tussauds New York Celebrity Wax Museum
NYC: Museum of Modern Art

NYC: Museum of Modern Art (MoMA) Entry Ticket

฿931
per adult
92% of travellers recommend
NYC: Museum of Modern Art (MoMA) Entry Ticket
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.

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.