$39 Cheap flight deals from Chicago (CHI) to Port Jefferson (NYC)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Port Jefferson

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, May 9 - Wed, May 14
ORD
O'Hare Intl.
LGA
LaGuardia
$203 Roundtrip, just found
$203
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 9 from O'Hare Intl. to LaGuardia, returning Wed, May 14, priced at $203 just found
Fri, May 9 - Wed, May 28
MDW
Midway Intl.
ISP
MacArthur
$221 Roundtrip, found 6 days ago
$221
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, May 9 from Midway Intl. to MacArthur, returning Wed, May 28, priced at $221 found 6 days ago
Fri, May 9 - Tue, May 13
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$221 Roundtrip, just found
$221
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, May 9 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Tue, May 13, priced at $221 just found
Sat, May 10 - Sat, May 17
ORD
O'Hare Intl.
ISP
MacArthur
$233 Roundtrip, found 21 hours ago
$233
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sat, May 10 from O'Hare Intl. to MacArthur, returning Sat, May 17, priced at $233 found 21 hours ago

Airfares from $39 One Way, $80 Round Trip from Chicago to Port Jefferson

Prices starting at $80 for return flights and $39 for one-way flights to Port Jefferson were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, May 31 - Tue, Jun 3
ORD
Chicago
EWR
New York
$80 Roundtrip, found 1 hour ago
$80
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, May 31 from Chicago to New York, returning Tue, Jun 3, priced at $80 found 1 hour ago
Tue, May 27 - Sat, May 31
ORD
Chicago
LGA
New York
$80 Roundtrip, found 4 days ago
$80
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, May 27 from Chicago to New York, returning Sat, May 31, priced at $80 found 4 days ago
Thu, Jun 5 - Sun, Jun 8
ORD
Chicago
HVN
New Haven
$90 Roundtrip, just found
$90
Roundtrip
just found
Select Avelo Airlines flight, departing Thu, Jun 5 from Chicago to New Haven, returning Sun, Jun 8, priced at $90 just found
Tue, Jul 8 - Tue, Jul 15
ORD
Chicago
LGA
New York
$105 Roundtrip, just found
$105
Roundtrip
just found
Select Delta flight, departing Tue, Jul 8 from Chicago to New York, returning Tue, Jul 15, priced at $105 just found
Tue, Jun 17 - Tue, Jun 24
ORD
Chicago
JFK
New York
$107 Roundtrip, found 6 hours ago
$107
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Jun 17 from Chicago to New York, returning Tue, Jun 24, priced at $107 found 6 hours ago

Port Jefferson economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James
2.5-star property

Hotel St. James

8.6/10 Excellent! (5,920 reviews)

Jun 23 - Jun 27

4 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Clean and excellent location.

Reviewed on Apr 22, 2025

1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

8.8/10 Excellent! (1,010 reviews)

Jun 8 - Jun 11

3 night stay

Chicago (ORD) to New York (JFK)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 20 hours ago
The hotel is beautiful looking forward to visiting again.

Reviewed on Feb 21, 2023

INNSiDE by Meliá New York Nomad
4.5-star property

INNSiDE by Meliá New York Nomad

9/10 Wonderful! (2,214 reviews)

Jun 23 - Jun 27

4 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Very pricey. By the time you add on all the taxes and fees, plus a $91 "facility fee" (for bottled water, the gym, etc., which I didn't use any of) the price was doubled from what it started at. Why wasn't the facility fee just incorporated into the room price, if it is going to get tacked on anyway? At least that way you would know up front what you are required to pay. I didn't even here about the facility fee until I checked in.

Reviewed on Apr 13, 2025

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

Port Jefferson packages with premium economy flights

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

9/10 Wonderful! (3,632 reviews)

Jun 6 - Jun 9

3 night stay

Chicago (CHI) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
The staff was amazing! They went above and beyond for my husband who uses a walker. They were so kind and super efficient!

Reviewed on Apr 3, 2025

The Fifth Avenue Hotel
5.0-star property

The Fifth Avenue Hotel

9.6/10 Exceptional! (76 reviews)

Jun 6 - Jun 9

3 night stay

Chicago (CHI) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
The Manner in the Unbound Collection by Hyatt
5.0-star property

The Manner in the Unbound Collection by Hyatt

9.4/10 Exceptional! (24 reviews)

Jun 6 - Jun 9

3 night stay

Chicago (CHI) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Chicago to Port Jefferson
View all trips

Port Jefferson first class 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

8/10 Very Good! (4,892 reviews)

Jun 19 - Jun 22

3 night stay

Chicago (CHI) to New York (JFK)

American Airlines • Roundtrip • FirstClass
per person
found 8 hours ago
Great location and convenience to Grand Central terminal!

Reviewed on Apr 28, 2025

The Manner in the Unbound Collection by Hyatt
5.0-star property

The Manner in the Unbound Collection by Hyatt

9.4/10 Exceptional! (24 reviews)

Jun 19 - Jun 22

3 night stay

Chicago (CHI) to New York (JFK)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
per person
found 8 hours ago
The Langham, New York, Fifth Avenue
5.0-star property

The Langham, New York, Fifth Avenue

9.4/10 Exceptional! (1,000 reviews)

Jun 19 - Jun 22

3 night stay

Chicago (CHI) to New York (JFK)

American Airlines • Roundtrip • FirstClass
per person
found 8 hours ago
Great communication prior to visit, requested 1 hour early check in and was assured it wouldnt be a problem. Arrived at 5 minutes past regular check in time and was told suite wasnt ready🙄 Didnt put out do not disturb sign out which is my fault...but 3 different people disturbed us between 9am and 11am. Other than that very nice hotel and amazing view. Will stay again

Reviewed on Sep 28, 2024

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

More About Flying To Port Jefferson from Chicago

Route Information for Flights from Chicago to Port Jefferson

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

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.