$111 Cheap flight deals from Chicago (CHI) to Fire Island Pines (LGA)

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This Weekend's Flight Deals from Chicago to Fire Island Pines

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, Sep 11 - Sat, Sep 12
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$270 Roundtrip, found 1 hour ago
$270
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Sep 11 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Sat, Sep 12, priced at $270 found 1 hour ago
Sat, Sep 12 - Sat, Sep 19
MDW
Midway Intl.
LGA
LaGuardia
$297 Roundtrip, found 1 hour ago
$297
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, Sep 12 from Midway Intl. to LaGuardia, returning Sat, Sep 19, priced at $297 found 1 hour ago
Sat, Sep 12 - Tue, Sep 15
RFD
Greater Rockford
EWR
Newark Liberty Intl. Airport
$304 Roundtrip, found 4 days ago
$304
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Sep 12 from Greater Rockford to Newark Liberty Intl. Airport, returning Tue, Sep 15, priced at $304 found 4 days ago
Sat, Sep 12 - Tue, Sep 15
ORD
O'Hare Intl.
JFK
John F. Kennedy Intl.
$307 Roundtrip, found 1 hour ago
$307
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, Sep 12 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Sep 15, priced at $307 found 1 hour ago

Airfares from $111 One Way, $226 Round Trip from Chicago to Fire Island Pines

Prices starting at $226 for return flights and $111 for one-way flights to Fire Island Pines were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Sep 28 - Tue, Sep 29
ORD
Chicago
LGA
New York
$226 Roundtrip, found 1 hour ago
$226
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Chicago to New York, returning Tue, Sep 29, priced at $226 found 1 hour ago
Wed, Sep 23 - Sat, Sep 26
ORD
Chicago
EWR
New York
$226 Roundtrip, found 2 hours ago
$226
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Sep 23 from Chicago to New York, returning Sat, Sep 26, priced at $226 found 2 hours ago
Tue, Oct 27 - Fri, Oct 30
MDW
Chicago
EWR
New York
$232 Roundtrip, found 5 days ago
$232
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Chicago to New York, returning Fri, Oct 30, priced at $232 found 5 days ago
Tue, Sep 29 - Wed, Sep 30
MDW
Chicago
LGA
New York
$236 Roundtrip, found 1 hour ago
$236
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Sep 29 from Chicago to New York, returning Wed, Sep 30, priced at $236 found 1 hour ago
Sat, Sep 19 - Wed, Sep 23
ORD
Chicago
JFK
New York
$263 Roundtrip, found 2 hours ago
$263
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Sat, Sep 19 from Chicago to New York, returning Wed, Sep 23, priced at $263 found 2 hours ago

Fire Island Pines economy flight packages

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

Hotel Riu Plaza New York Times Square

9/10 Wonderful! (3,334 reviews)

Oct 9 - Oct 12

3 night stay

Chicago (CHI) to New York (JFK)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,612, price is now $991 per person
$991
per person
found 1 day ago
Clean, staff was attentive, breakfast is a bit chaotic, but food choices sufficient

Reviewed on Sep 5, 2026

Ink 48 Hotel
4.5-star property

Ink 48 Hotel

8.4/10 Very Good! (1,772 reviews)

Oct 17 - Oct 23

6 night stay

Chicago (CHI) to New York (JFK)

Southwest Airlines • Coach

New York (JFK) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $2,118, price is now $1,395 per person
$1,395
per person
found 1 day ago
Mucho ruido se escuha en las Habitaciones, imposible dormir...solicitamos un cambio de Habitacion y no fue atendida nuestra solicitud El Servicio del restaurante muy limitado

Reviewed on Sep 5, 2026

33 Hotel, New York City, Seaport
5.0-star property

33 Hotel, New York City, Seaport

9/10 Wonderful! (1,002 reviews)

Oct 22 - Oct 26

4 night stay

Chicago (CHI) to New York (JFK)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,644, price is now $1,084 per person
$1,084
per person
found 1 day ago

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Fire Island Pines first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Pergola JFK Airport
2.5-star property

Hotel Pergola JFK Airport

6.2/10 (2,350 reviews)

Oct 17 - Oct 21

4 night stay

Chicago (CHI) to New York (JFK)

Delta • FirstClass

New York (JFK) to Chicago (CHI)

American Airlines • FirstClass
Price was $2,325, price is now $1,928 per person
$1,928
per person
found 20 hours ago

6 Columbus Central Park Hotel
4.5-star property

6 Columbus Central Park Hotel

8.2/10 Very Good! (1,547 reviews)

Oct 17 - Oct 21

4 night stay

Chicago (CHI) to New York (JFK)

Delta • FirstClass

New York (JFK) to Chicago (CHI)

American Airlines • FirstClass
Price was $5,705, price is now $4,600 per person
$4,600
per person
found 20 hours ago

Hotel 57
4.0-star property

Hotel 57

8.2/10 Very Good! (1,101 reviews)

Oct 17 - Oct 21

4 night stay

Chicago (CHI) to New York (JFK)

Delta • FirstClass

New York (JFK) to Chicago (CHI)

American Airlines • FirstClass
Price was $2,494, price is now $2,103 per person
$2,103
per person
found 20 hours ago
Some rough edges but the staff were very engaging

Reviewed on Sep 4, 2026

Don't see what you're looking for?
See all available trips from Chicago to Fire Island Pines
View all trips

More About Flying To Fire Island Pines from Chicago

Route Information for Flights from Chicago to Fire Island Pines

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

Chicago to Fire Island Pines

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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.