$29 Cheap flight deals from Chicago (CHI) to Long Island (NYC)

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This Weekend's Flight Deals from Chicago to Long Island

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 2 - Mon, Jan 5
ORD
O'Hare Intl.
JFK
John F. Kennedy Intl.
$246 Roundtrip, found 1 hour ago
$246
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Jan 2 from O'Hare Intl. to John F. Kennedy Intl., returning Mon, Jan 5, priced at $246 found 1 hour ago
Fri, Jan 2 - Tue, Jan 6
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$276 Roundtrip, just found
$276
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jan 2 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Tue, Jan 6, priced at $276 just found
Fri, Jan 2 - Mon, Jan 5
MDW
Midway Intl.
LGA
LaGuardia
$316 Roundtrip, found 5 days ago
$316
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Jan 2 from Midway Intl. to LaGuardia, returning Mon, Jan 5, priced at $316 found 5 days ago
Fri, Jan 2 - Mon, Jan 5
RFD
Greater Rockford
LGA
LaGuardia
$340 Roundtrip, found 5 days ago
$340
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Jan 2 from Greater Rockford to LaGuardia, returning Mon, Jan 5, priced at $340 found 5 days ago

Airfares from $29 One Way, $58 Round Trip from Chicago to Long Island

Prices starting at $58 for return flights and $29 for one-way flights to Long Island were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Jan 29 - Thu, Feb 5
ORD
Chicago
JFK
New York
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jan 29 from Chicago to New York, returning Thu, Feb 5, priced at $58 just found
Thu, Jan 15 - Sun, Jan 18
MDW
Chicago
EWR
New York
$59 Roundtrip, just found
$59
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jan 15 from Chicago to New York, returning Sun, Jan 18, priced at $59 just found
Tue, Jan 20 - Wed, Jan 21
ORD
Chicago
LGA
New York
$67 Roundtrip, found 1 hour ago
$67
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Jan 20 from Chicago to New York, returning Wed, Jan 21, priced at $67 found 1 hour ago
Sat, Jan 24 - Thu, Jan 29
ORD
Chicago
EWR
New York
$72 Roundtrip, just found
$72
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jan 24 from Chicago to New York, returning Thu, Jan 29, priced at $72 just found
Sun, Jan 25 - Thu, Jan 29
MDW
Chicago
LGA
New York
$97 Roundtrip, found 6 hours ago
$97
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sun, Jan 25 from Chicago to New York, returning Thu, Jan 29, priced at $97 found 6 hours ago

Long Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad
4.5-star property

INNSiDE by Meliá New York Nomad

9.2/10 Wonderful! (2,008 reviews)

Jan 30 - Feb 2

3 night stay

Chicago (CHI) to New York (JFK)

Frontier Airlines • Coach

New York (JFK) to Chicago (CHI)

Spirit Airlines • Coach
Save 100% on your flight
Price was $581, price is now $346 per person
$346
per person
found 1 day ago
Very nice and helpful. Front desk , was the best service, all staff was great❤️

Reviewed on Dec 25, 2025

Topping Rose House
4.5-star property

Topping Rose House

9.2/10 Wonderful! (136 reviews)

Feb 5 - Feb 8

3 night stay

Chicago (ORD) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Price was $1,004, price is now $375 per person
$375
per person
just found
Breakfast and lunch not as good as dinner. Lawn mowing distracting during breakfast

Reviewed on Jul 8, 2019

The Inn At Fox Hollow Hotel
4.0-star property

The Inn At Fox Hollow Hotel

9.2/10 Wonderful! (1,002 reviews)

Feb 12 - Feb 15

3 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $671, price is now $373 per person
$373
per person
found 1 day ago
Very nice and clean large rooms

Reviewed on Jan 21, 2025

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Long Island packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel
4.0-star property

Sheraton New York Times Square Hotel

7.4/10 Good! (5,413 reviews)

Feb 23 - Feb 27

4 night stay

Chicago (CHI) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
Price was $761, price is now $522 per person
$522
per person
found 1 day ago
Close to attractions. Staff was helpful and knowledgeable.

Reviewed on Dec 26, 2025

INNSiDE by Meliá New York Nomad
4.5-star property

INNSiDE by Meliá New York Nomad

9.2/10 Wonderful! (2,008 reviews)

Feb 23 - Feb 27

4 night stay

Chicago (CHI) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $864, price is now $582 per person
$582
per person
found 1 day ago
Very nice and helpful. Front desk , was the best service, all staff was great❤️

Reviewed on Dec 25, 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)

Feb 23 - Feb 27

4 night stay

Chicago (CHI) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,025, price is now $731 per person
$731
per person
found 1 day ago
Amazing staff and great location

Reviewed on Dec 28, 2025

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Long Island first class flight packages

Price found within the past 48 hours. Click for updated prices.
Courtyard New York Manhattan/ Midtown East
3.0-star property

Courtyard New York Manhattan/ Midtown East

9/10 Wonderful! (2,346 reviews)

Feb 23 - Feb 25

2 night stay

Chicago (CHI) to New York (JFK)

Delta • Roundtrip • FirstClass
Price was $1,062, price is now $747 per person
$747
per person
found 1 day ago
The staff was always professional and friendly.

Reviewed on Oct 6, 2025

1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

8.8/10 Excellent! (1,000 reviews)

Jan 29 - Feb 3

5 night stay

Chicago (ORD) to New York (JFK)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,502, price is now $1,636 per person
$1,636
per person
found 1 day ago
The hotel is beautiful looking forward to visiting again.

Reviewed on Feb 21, 2023

DoubleTree by Hilton New York JFK Airport
3.5-star property

DoubleTree by Hilton New York JFK Airport

8/10 Very Good! (1,105 reviews)

Jan 30 - Feb 7

8 night stay

Chicago (ORD) to New York (JFK)

American Airlines • Roundtrip • FirstClass
Price was $1,400, price is now $1,039 per person
$1,039
per person
found 18 hours ago
The AC was making noise, the hotel staff was not able to fix the issue

Reviewed on Dec 8, 2025

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More About Flying To Long Island from Chicago

Route Information for Flights from Chicago to Long Island

Origin Airport IATA Code
CHI
Destination Airport IATA Code
NYC
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Long Island

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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.