$93 Cheap flight deals from Chicago (CHI) to Syosset (NYC)

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This Weekend's Flight Deals from Chicago to Syosset

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, Oct 23 - Fri, Oct 30
MDW
Midway Intl.
LGA
LaGuardia
$286 Roundtrip, just found
$286
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Oct 23 from Midway Intl. to LaGuardia, returning Fri, Oct 30, priced at $286 just found
Sat, Oct 24 - Wed, Oct 28
ORD
O'Hare Intl.
LGA
LaGuardia
$310 Roundtrip, found 3 hours ago
$310
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Oct 24 from O'Hare Intl. to LaGuardia, returning Wed, Oct 28, priced at $310 found 3 hours ago
Fri, Oct 23 - Sun, Oct 25
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$356 Roundtrip, just found
$356
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Oct 23 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Sun, Oct 25, priced at $356 just found
Fri, Oct 23 - Sun, Oct 25
ORD
O'Hare Intl.
JFK
John F. Kennedy Intl.
$374 Roundtrip, just found
$374
Roundtrip
just found
Select American Airlines flight, departing Fri, Oct 23 from O'Hare Intl. to John F. Kennedy Intl., returning Sun, Oct 25, priced at $374 just found

Airfares from $93 One Way, $203 Round Trip from Chicago to Syosset

Prices starting at $203 for return flights and $93 for one-way flights to Syosset were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Dec 8 - Sat, Dec 12
ORD
Chicago
EWR
New York
$203 Roundtrip, found 13 hours ago
$203
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Dec 8 from Chicago to New York, returning Sat, Dec 12, priced at $203 found 13 hours ago
Tue, Nov 17 - Wed, Nov 18
MDW
Chicago
LGA
New York
$220 Roundtrip, found 2 hours ago
$220
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Chicago to New York, returning Wed, Nov 18, priced at $220 found 2 hours ago
Tue, Dec 8 - Sat, Dec 12
MDW
Chicago
EWR
New York
$220 Roundtrip, found 5 hours ago
$220
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Dec 8 from Chicago to New York, returning Sat, Dec 12, priced at $220 found 5 hours ago
Wed, Dec 2 - Sat, Dec 5
ORD
Chicago
LGA
New York
$220 Roundtrip, found 6 hours ago
$220
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Chicago to New York, returning Sat, Dec 5, priced at $220 found 6 hours ago
Tue, Dec 1 - Mon, Dec 7
ORD
Chicago
JFK
New York
$297 Roundtrip, found 5 hours ago
$297
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Dec 1 from Chicago to New York, returning Mon, Dec 7, priced at $297 found 5 hours ago

Syosset economy flight packages

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

Hotel Riu Plaza Manhattan Times Square

9.2/10 Wonderful! (4,026 reviews)

Nov 22 - Nov 26

4 night stay

Chicago (CHI) to New York (JFK)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,437, price is now $964 per person
$964
per person
found 1 day ago
Me and my family were very satisfied with our stay at the RIU. It was very clean and our room was cleaned daily and we were left with plenty of clean towels. The location was also perfect for what we were there for.

Reviewed on Oct 18, 2026

1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

9/10 Wonderful! (1,007 reviews)

Nov 24 - Nov 30

6 night stay

Chicago (ORD) to New York (JFK)

United • Roundtrip • Coach
Save 100% on your flight
Price was $4,600, price is now $2,788 per person
$2,788
per person
found 2 days ago
My room had great views and was clean and fun.

Reviewed on Oct 15, 2026

Hotel Beacon
4.0-star property

Hotel Beacon

9.4/10 Exceptional! (1,530 reviews)

Dec 3 - Dec 6

3 night stay

Chicago (CHI) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,976, price is now $1,319 per person
$1,319
per person
found 1 day ago
The Bevin was clean, quiet and comfortable but is undergoing renovations o just felt like a place to sleep not a luxury NYC hotel.

Reviewed on Oct 18, 2026

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Syosset packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Sela V Hotel
4.0-star property

Sela V Hotel

9.4/10 Exceptional! (284 reviews)

Dec 5 - Dec 7

2 night stay

Chicago (MDW) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $978, price is now $824 per person
$824
per person
found 1 day ago
Excelente hotel con conveniente ubicación

Reviewed on Oct 18, 2026

Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

9.2/10 Wonderful! (4,026 reviews)

Nov 19 - Nov 22

3 night stay

Chicago (MDW) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,836, price is now $1,271 per person
$1,271
per person
found 2 hours ago
Me and my family were very satisfied with our stay at the RIU. It was very clean and our room was cleaned daily and we were left with plenty of clean towels. The location was also perfect for what we were there for.

Reviewed on Oct 18, 2026

Margaritaville Resort Times Square
4.0-star property

Margaritaville Resort Times Square

9/10 Wonderful! (4,269 reviews)

Nov 19 - Nov 22

3 night stay

Chicago (MDW) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,130, price is now $975 per person
$975
per person
found 2 hours ago

Don't see what you're looking for?
See all available trips from Chicago to Syosset
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Syosset first class flight packages

Price found within the past 48 hours. Click for updated prices.
NEW YORKER BY LOTTE HOTELS
4.0-star property

NEW YORKER BY LOTTE HOTELS

8.2/10 Very Good! (7,349 reviews)

Nov 25 - Nov 28

3 night stay

Chicago (CHI) to New York (JFK)

Frontier Airlines • Non-stop • FirstClass

New York (JFK) to Chicago (CHI)

American Airlines • Non-stop • FirstClass
Price was $1,747, price is now $1,325 per person
$1,325
per person
found 1 day ago
It was lovely, everyone was very helpful. We loved the location so near MSG.

Reviewed on Oct 18, 2026

Park Lane New York
5.0-star property

Park Lane New York

8.4/10 Very Good! (1,813 reviews)

Dec 10 - Dec 13

3 night stay

Chicago (ORD) to New York (JFK)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,713, price is now $1,865 per person
$1,865
per person
found 3 hours ago

Hotel Beacon
4.0-star property

Hotel Beacon

9.4/10 Exceptional! (1,530 reviews)

Dec 10 - Dec 13

3 night stay

Chicago (ORD) to New York (JFK)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,054, price is now $1,568 per person
$1,568
per person
found 3 hours ago
The Bevin was clean, quiet and comfortable but is undergoing renovations o just felt like a place to sleep not a luxury NYC hotel.

Reviewed on Oct 18, 2026

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

More About Flying To Syosset from Chicago

Route Information for Flights from Chicago to Syosset

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

Chicago to Syosset

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Discount Travel Planning Made Simple

You will have no problems finding budget flights from Chicago to Syosset on Orbitz.com. If your travel plans are flexible, you can search for fares three days before and after a specific date to find the best price.

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.