$28 Cheap flight deals from Chicago (CHI) to Southold (LGA)

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This Weekend's Flight Deals from Chicago to Southold

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, Nov 29 - Mon, Dec 2
ORD
O'Hare Intl.
LGA
LaGuardia
$268 Roundtrip, just found
$268
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Nov 29 from O'Hare Intl. to LaGuardia, returning Mon, Dec 2, priced at $268 just found
Fri, Nov 29 - Thu, Dec 5
MDW
Midway Intl.
LGA
LaGuardia
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Nov 29 from Midway Intl. to LaGuardia, returning Thu, Dec 5, priced at $299 found 1 day ago
Sun, Dec 1 - Wed, Dec 4
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$302 Roundtrip, just found
$302
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Dec 1 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Wed, Dec 4, priced at $302 just found
Sat, Nov 30 - Thu, Dec 5
MDW
Midway Intl.
JFK
John F. Kennedy Intl.
$463 Roundtrip, found 1 day ago
$463
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 30 from Midway Intl. to John F. Kennedy Intl., returning Thu, Dec 5, priced at $463 found 1 day ago

Airfares from $28 One Way, $110 Round Trip from Chicago to Southold

Prices starting at $110 for return flights and $28 for one-way flights to Southold 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, Feb 4 - Tue, Feb 11
ORD
Chicago
LGA
New York
$110 Roundtrip, found 5 hours ago
$110
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Feb 4 from Chicago to New York, returning Tue, Feb 11, priced at $110 found 5 hours ago
Mon, Feb 3 - Tue, Feb 11
MDW
Chicago
LGA
New York
$114 Roundtrip, found 19 hours ago
$114
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Mon, Feb 3 from Chicago to New York, returning Tue, Feb 11, priced at $114 found 19 hours ago
Thu, Jan 30 - Wed, Feb 5
MDW
Chicago
JFK
New York
$114 Roundtrip, found 13 hours ago
$114
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Jan 30 from Chicago to New York, returning Wed, Feb 5, priced at $114 found 13 hours ago
Mon, Jan 27 - Wed, Feb 5
ORD
Chicago
JFK
New York
$114 Roundtrip, found 19 hours ago
$114
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Mon, Jan 27 from Chicago to New York, returning Wed, Feb 5, priced at $114 found 19 hours ago
Wed, Dec 11 - Tue, Feb 11
MDW
Chicago
EWR
New York
$115 Roundtrip, found 3 days ago
$115
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Dec 11 from Chicago to New York, returning Tue, Feb 11, priced at $115 found 3 days ago

Southold economy flight packages

Price found within the past 48 hours. Click for updated prices.
Millennium Hilton New York One UN Plaza
4.0-star property

Millennium Hilton New York One UN Plaza

8.2/10 Very Good! (1,469 reviews)

Dec 29 - Jan 4

6 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Near the United Nations

Reviewed on Oct 18, 2024

The William Vale
5.0-star property

The William Vale

8.6/10 Excellent! (1,000 reviews)

Dec 29 - Jan 4

6 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
per person
found 1 day ago
The music from the club was very loud the whole night. The rooms were very small even though I had reserved a higher category room. The front desk also would not move us to a bigger room when asked. I was not impressed. It was just OK

Reviewed on Jun 9, 2024

1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

8.6/10 Excellent! (1,003 reviews)

Dec 29 - Jan 4

6 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The hotel is beautiful looking forward to visiting again.

Reviewed on Feb 21, 2023

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Southold packages with premium economy flights

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

Westgate New York Grand Central

9/10 Wonderful! (1,966 reviews)

Dec 30 - Jan 2

3 night stay

Chicago (CHI) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
per person
found 5 hours ago
The Westgate was a great location for the New York City marathon. It was so easy to walk to see the runners and get to the finish line. Also fairly convenient to get to the theater district, subway, and restaurants. Our room was clean, a nice size, and comfortable. Hotel staff were extremely courteous and helpful.

Reviewed on Nov 6, 2024

The New York EDITION
5.0-star property

The New York EDITION

9/10 Wonderful! (414 reviews)

Dec 30 - Jan 2

3 night stay

Chicago (CHI) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 5 hours ago
The smell was amazing and the staff was very welcoming and accommodating. The property is gorgeous and so conveniently located. They give a credit every night at the lobby bar or spa fo offset the cost of the daily fee which is really nice. Will definitely stay there when I’m in NYC next time.

Reviewed on Aug 7, 2024

PUBLIC, an Ian Schrager hotel
4.0-star property

PUBLIC, an Ian Schrager hotel

8.2/10 Very Good! (2,618 reviews)

Dec 30 - Jan 2

3 night stay

Chicago (CHI) to New York (JFK)

Delta • Roundtrip • PremiumEconomy
per person
found 5 hours ago
We appreciated the cleaniness, efficiency and conveince of this hotel. The room was very clean and we liked that the floors were uncarpeted. We also enjoyed lying in bed, while taking in the view of the NYC skyline. The room was small, but well laid out. We could store our suitcases under the bench to keep them out of the way. In addition, there were areas to work in the second floor lobby and we could grab breakfast at the downstairs counter-service restaurant. The hotel location is walking distances to several subway lines and good restaurants. We will stay here again.

Reviewed on Sep 25, 2024

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Southold first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hudson Yards Hotel
2.0-star property

Hudson Yards Hotel

7.2/10 Good! (47 reviews)

Dec 29 - Jan 1

3 night stay

Chicago (ORD) to New York (JFK)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
The property is conveniently located, accessible by multiple subway lines and buses. The property itself is fairly well kept. The biggest plus is the staff, who are friendly and helpful. But the rooms are not especially welcoming. No plastic cups in the room, so if you're thirsty, or want to rinse your mouth after brushing your teeth, you're using your hands as a cup or sticking your mouth under the running tap. No coffee maker in the room, or an iron, ironing board, hair dryer--not even a phone!--stuff that you would normally see in a hotel room. Noisy in-window AC units, the air flow from which is blocked by the blackout curtains. Those curtains are handy, though, as the room window faces onto a hallway and anyone walking by could look right into the room if the curtain wasn't pulled down. The bathroom also functions as the closet/storage space, because the room is absolutely dominated by the bed. Other reviews have said that the place feels institutional, which I'd have to agree with, which makes the room price seem like an outrage. You're paying for location and not much else.

Reviewed on Nov 3, 2024

The New York EDITION
5.0-star property

The New York EDITION

9/10 Wonderful! (414 reviews)

Dec 29 - Jan 1

3 night stay

Chicago (ORD) to New York (JFK)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
per person
found 1 day ago
The smell was amazing and the staff was very welcoming and accommodating. The property is gorgeous and so conveniently located. They give a credit every night at the lobby bar or spa fo offset the cost of the daily fee which is really nice. Will definitely stay there when I’m in NYC next time.

Reviewed on Aug 7, 2024

The Langham, New York, Fifth Avenue
5.0-star property

The Langham, New York, Fifth Avenue

9.4/10 Exceptional! (1,000 reviews)

Dec 29 - Jan 1

3 night stay

Chicago (ORD) to New York (JFK)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
per person
found 1 day 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

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More About Flying To Southold from Chicago

Route Information for Flights from Chicago to Southold

Origin Airport IATA Code
CHI
Destination Airport IATA Code
LGA
Distance
737 mi
Direct Flight Airlines
American Airlines, Qatar Airways, KLM, Air France, Kenya Airways, Delta Air Lines, Gol, Alaska Airlines, Royal Air Maroc, JetBlue, LATAM Airlines, Finnair, SAS, Iberia, ITA Airways, Korean Air, TAP Air Portugal, WestJet, Virgin Atlantic, Singapore Airlines, British Airways
Earliest Flight Arrival
3:30PM UTC
Latest Flight Arrival
12:52AM UTC

Chicago to Southold

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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.