Cheap flights To City Island (NYC) from $28

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Cheap Flights to City Island from $28 One Way, $56 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Apr 21 - Sat, Apr 25
ORD
O'Hare Intl.
JFK
John F. Kennedy Intl.
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Apr 21 from O'Hare Intl. to John F. Kennedy Intl., returning Sat, Apr 25, priced at $56 just found
Sat, Apr 18 - Sat, Apr 25
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$58 Roundtrip, found 1 hour ago
$58
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Apr 18 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Sat, Apr 25, priced at $58 found 1 hour ago
Tue, May 12 - Tue, May 19
ORD
O'Hare Intl.
LGA
LaGuardia
$72 Roundtrip, found 11 hours ago
$72
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Tue, May 12 from O'Hare Intl. to LaGuardia, returning Tue, May 19, priced at $72 found 11 hours ago
Mon, May 11 - Sat, May 16
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$123 Roundtrip, found 18 hours ago
$123
Roundtrip
found 18 hours ago
Select United flight, departing Mon, May 11 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Sat, May 16, priced at $123 found 18 hours ago
Tue, Mar 3 - Tue, Mar 17
LAX
Los Angeles Intl.
EWR
Newark Liberty Intl. Airport
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Mar 3 from Los Angeles Intl. to Newark Liberty Intl. Airport, returning Tue, Mar 17, priced at $137 found 2 days ago
Tue, Jun 2 - Wed, Jun 3
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jun 2 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Wed, Jun 3, priced at $137 found 5 days ago
Mon, Apr 27 - Tue, Apr 28
ORD
O'Hare Intl.
JFK
John F. Kennedy Intl.
$147 Roundtrip, found 17 hours ago
$147
Roundtrip
found 17 hours ago
Select Delta flight, departing Mon, Apr 27 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Apr 28, priced at $147 found 17 hours ago
Wed, Apr 15 - Wed, Apr 22
ORD
O'Hare Intl.
JFK
John F. Kennedy Intl.
$152 Roundtrip, just found
$152
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Apr 15 from O'Hare Intl. to John F. Kennedy Intl., returning Wed, Apr 22, priced at $152 just found
Tue, May 12 - Wed, May 20
LAX
Los Angeles Intl.
LGA
LaGuardia
$177 Roundtrip, found 3 hours ago
$177
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, May 12 from Los Angeles Intl. to LaGuardia, returning Wed, May 20, priced at $177 found 3 hours ago
Sun, Apr 26 - Thu, Apr 30
SFO
San Francisco Intl.
JFK
John F. Kennedy Intl.
$200 Roundtrip, just found
$200
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Apr 26 from San Francisco Intl. to John F. Kennedy Intl., returning Thu, Apr 30, priced at $200 just found

City Island Flight Information

Traveling To
City Island
Destination Airport IATA Code
NYC
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Delta, American Airlines, JetBlue Airways, United
Flight Price
$56
Earliest Departing Flight
Latest Departing Flight

Flights Review

Oct 14, 2019

Newark airport is a pain...but it's not United's fault. The actual flight was just fine.

A verified traveler
Philadelphia to Newark · United

Book Your Flight & Hotel Together & Save

City Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Grand Central New York
4.0-star property

Hyatt Grand Central New York

Mar 26 - Mar 30

4 night stay

Dallas (DAL) to New York (JFK)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,004, price is now $633 per person
$633
per person
found 1 day ago
Lotte New York Palace
4.5-star property

Lotte New York Palace

Apr 6 - Apr 11

5 night stay

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Coach

Newark Liberty Intl. Airport (EWR) to Dallas (DFW)

Frontier Airlines • Coach
Price was $2,128, price is now $1,363 per person
$1,363
per person
found 1 day ago
Loews Regency New York Hotel
5.0-star property

Loews Regency New York Hotel

Mar 20 - Mar 27

7 night stay

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,199, price is now $2,089 per person
$2,089
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Dallas to City Island
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City Island premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Grand Central New York
4.0-star property

Hyatt Grand Central New York

8.2/10 Very Good! (6,333 reviews)

Apr 4 - Apr 8

4 night stay

Dallas (DFW) to New York (JFK)

Spirit Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,035, price is now $640 per person
$640
per person
found 1 day ago
Great hotel! Very convenient

Reviewed on Feb 2, 2026

Lotte New York Palace
4.5-star property

Lotte New York Palace

9/10 Wonderful! (1,723 reviews)

Apr 4 - Apr 8

4 night stay

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,829, price is now $1,250 per person
$1,250
per person
found 1 day ago
We stay here almost very year and would not think of staying anywhere else!

Reviewed on Jun 15, 2025

Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

9/10 Wonderful! (2,790 reviews)

Apr 4 - Apr 8

4 night stay

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,539, price is now $1,057 per person
$1,057
per person
found 1 day ago
Beautiful room and great customer service

Reviewed on Feb 7, 2026

Don't see what you're looking for?
See all available trips from Dallas to City Island
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City Island

If you are looking for affordable flights to City Island, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to City Island now available

As you review your budget and travel plans, consider the low fares Orbitz offers on City Island flights. With Orbitz, booking flights to City Island is easy and the lowest prices are guaranteed.

Easy self-help service offered

Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your City Island flights by visiting the Orbitz site or mobile application.

Orbitz looks after you

Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on City Island flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.

Traveler profile updates

After booking your City Island flights, you may access your account profile on the Orbitz site and update your frequent flyer or loyalty membership details. This information will remain on the system and will be available for you to access when you make any future bookings with Orbitz.

Frequently asked questions

How much is a flight to City Island?
Prices for return flights to City Island this week ranged between $56 and $200. If you were flying one-way from Chicago (ORD), you could have snapped up ticket prices from just $28.
How to book the cheapest flight to City Island?
With some of the biggest and best flight deals around, a bargain is always waiting for you with Orbitz. The following handy hints will help you pick up cheap flights to City Island — and leave you with more money to play with:

  • Depending on where you're coming from, click on the 'Nearby airports' function (located under the departure and arrival form fields). At times, other departure points will have more competitive fares.
  • If you're flexible with your travel plans, click on the 'Show flexible dates' link. It'll bring up flight deals for the days before and after your selected departure. Ticket prices often vary depending on what day it is.
  • To filter your results, hit 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also choose whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • The early bird catches the most rewarding deals, so book as soon as you've worked out your travel dates. The most affordable fares get snapped up first and prices normally increase as the departure date nears.
  • Combine your hotels, flights and car rentals into an impressive package deal. Save your cash for things that really excite you, like discovering every corner of City Island.
  • Don't travel during peak seasons if you can. By steering clear of summer and school vacations, you can save plenty on your airfares.

How long is a flight to City Island?
Where you're leaving from and if you have a layover help determine your flight time. However, these busy routes to City Island will give you a better picture:

  • Los Angeles, CA (LAX-Los Angeles Intl.) to John F. Kennedy Intl. Airport (JFK) - 5 hours and 26 minutes
  • San Francisco, CA (SFO-San Francisco Intl.) to John F. Kennedy Intl. Airport (JFK) - 5 hours
  • Boston, MA (BOS-Logan Intl.) to John F. Kennedy Intl. Airport (JFK) - 1 hour and 20 minutes

What is the best time to book a flight to City Island?
Purchase your seats to City Island in January. This is the ideal time of the year for bargain fares, closely followed by February and August. Pick up cheap flights and enjoy your dream vacation with Orbitz.
What day of the week is the cheapest to book a flight to City Island?
If you're after cheap airfares to City Island, the best days to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and some good timing!), a superb flight deal will be all yours.
What is the cheapest day of the week to fly to City Island?
According to Orbitz data from 2020, you'll want to kick off your vacation on a Monday to get cheap flights to City Island. Next most affordable day? Tuesday. Saturday will set you back the most. So, leave early in the week if you'd like to score a bargain fare without paying premium prices.
What is the cheapest month to fly to City Island?
Travel sometime in August if you're sticking to a budget. Orbitz data has found that it's generally the best month for cheap flights to City Island. June is when prices hit their peak.
Which airlines allow free cancellation?
Plans change, and we think your flight should be able to do the same. That's why Orbitz makes it a breeze to search for airlines with no change fees and free cancellation. Just enter your departure and arrival destinations and then choose "Filter by flexible change policies." How's that for fuss-free?
What do I need for the flight to City Island?
From onboard activities to travel basics like noise-canceling headphones, there are a few things a regular flyer won't take off without. To make sure you're ready for your journey, have a read through this useful list:

  • For starters, you'll need to take all relevant travel documents and some identification. How much is dependent on where you're taking off from. When booking, you should always use the exact name, birth date and gender listed on your current ID.
  • A well-packed carry-on bag is the key to a comfortable flight experience. Given your flight to City Island is no quick hop, take enough snacks and things to keep you occupied. A good book or magazine will help you pass the time.
  • Plane cabins are frequently quite cold. If you decide to fly during the peak of the City Island summer, be sure to take some warm clothes just in case.

How many direct flights are there to City Island?
At the moment, there are 1,485 direct flights every month to City Island. When it comes to airlines that will take you there, you're spoiled for choice. Delta Air Lines, JetBlue Airways and American Airlines are among the most sought-after. Alaska Airlines, British Airways and Air France are a few other respected carriers that provide nonstop services.
How do I get cheap first-class/business deals to City Island?
There are ways of booking first or business-class tickets to City Island that won't burn a hole through your budget. Bag a seat in the pointy end of the plane for less with these useful tips:

  • Be flexible with your travel dates and hold out for sales or exclusive offers on business or first-class airfares.
  • Find a low-cost carrier that has business-class seats. They usually come with more legroom and a glass of Champagne — but at a more affordable price.
  • Bid for an upgrade. Some airlines hold online auctions that let you put down a price for a seat at the front of the plane. You can also try upgrading with points earned through a flight loyalty scheme.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.