$33 Cheap flight deals from Chicago (CHI) to Southampton (LGA)

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This Weekend's Flight Deals from Chicago to Southampton

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.

Sat, Dec 13 - Tue, Dec 16
RFD
Greater Rockford
LGA
LaGuardia
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Greater Rockford to LaGuardia, returning Tue, Dec 16, priced at $152 found 3 days ago
Sat, Dec 13 - Tue, Dec 16
MDW
Midway Intl.
EWR
Newark Liberty Intl. Airport
$161 Roundtrip, found 3 days ago
$161
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Dec 13 from Midway Intl. to Newark Liberty Intl. Airport, returning Tue, Dec 16, priced at $161 found 3 days ago
Sat, Dec 13 - Mon, Dec 15
ORD
O'Hare Intl.
JFK
John F. Kennedy Intl.
$171 Roundtrip, just found
$171
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Dec 13 from O'Hare Intl. to John F. Kennedy Intl., returning Mon, Dec 15, priced at $171 just found
Fri, Dec 12 - Thu, Dec 25
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$188 Roundtrip, just found
$188
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Dec 12 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Thu, Dec 25, priced at $188 just found

Airfares from $33 One Way, $65 Round Trip from Chicago to Southampton

Prices starting at $65 for return flights and $33 for one-way flights to Southampton 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, Jan 13 - Thu, Jan 15
MDW
Chicago
EWR
New York
$65 Roundtrip, just found
$65
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jan 13 from Chicago to New York, returning Thu, Jan 15, priced at $65 just found
Sat, Jan 24 - Mon, Feb 2
ORD
Chicago
EWR
New York
$70 Roundtrip, found 6 days ago
$70
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sat, Jan 24 from Chicago to New York, returning Mon, Feb 2, priced at $70 found 6 days ago
Tue, Feb 3 - Mon, Feb 9
ORD
Chicago
LGA
New York
$72 Roundtrip, just found
$72
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Feb 3 from Chicago to New York, returning Mon, Feb 9, priced at $72 just found
Tue, Mar 3 - Thu, Mar 5
ORD
Chicago
LGA
New York
$91 Roundtrip, found 6 days ago
$91
Roundtrip
found 6 days ago
Select United flight, departing Tue, Mar 3 from Chicago to New York, returning Thu, Mar 5, priced at $91 found 6 days ago
Tue, Feb 3 - Mon, Feb 9
MDW
Chicago
LGA
New York
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Feb 3 from Chicago to New York, returning Mon, Feb 9, priced at $138 just found

Southampton economy flight packages

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)

Jan 30 - Feb 2

3 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Coach

New York (JFK) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $427, price is now $248 per person
$248
per person
found 1 day ago
The elevators didn’t work most of the time, and the waits were 10-15 minutes to get an elevator. The room was dated and small for the price I paid, but they were very clean.

Reviewed on Nov 23, 2025

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 (NYC)

Spirit Airlines • Coach

New York (NYC) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $573, price is now $334 per person
$334
per person
found 1 day ago
Great place. Would definitely stay there again. Only suggestion would be to keep the lobby bar open longer.

Reviewed on May 12, 2025

JW Marriott Essex House New York
4.5-star property

JW Marriott Essex House New York

8.8/10 Excellent! (1,001 reviews)

Jan 29 - Feb 1

3 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,039, price is now $644 per person
$644
per person
found 10 hours ago
Amazing location and very friendly staff. The hotel and rooms are very clean. However, the bedding felt stiff and not very comfortable. The pull out sofa mattress is not comfortable at all.

Reviewed on Jul 7, 2025

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Southampton packages with premium economy flights

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

Hotel St. James

8.8/10 Excellent! (6,546 reviews)

Jan 30 - Feb 1

2 night stay

Chicago (CHI) to New York (NYC)

Delta • Roundtrip • PremiumEconomy
Price was $556, price is now $452 per person
$452
per person
found 1 day ago
Genuinely loved this quaint little place! The staff were very friendly. I only gave the overall rating a 4 due to the old furniture and uncomfortable mattress in the room. Rooms need a coffee pot and new furniture and this place would be perfect. Honestly though, it wouldn’t keep us from booking there again. The location truly couldn’t get any better! We walked everywhere.

Reviewed on Nov 28, 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)

Jan 30 - Feb 1

2 night stay

Chicago (CHI) to New York (NYC)

Delta • Roundtrip • PremiumEconomy
Price was $653, price is now $512 per person
$512
per person
found 1 day ago
The hotel is clean and beautiful and in close proximity to subway. The staff was excellent. My only complaint was the breakfast was very crowded and ran out of food items both days I was there.

Reviewed on Dec 8, 2025

Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

9.2/10 Wonderful! (3,348 reviews)

Jan 30 - Feb 1

2 night stay

Chicago (CHI) to New York (NYC)

Delta • Roundtrip • PremiumEconomy
Price was $646, price is now $507 per person
$507
per person
found 1 day ago
Everything was good except the elevators were terrible. The wait for the elevators was ridiculous!

Reviewed on Jun 28, 2025

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Southampton first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Langham, New York, Fifth Avenue
5.0-star property

The Langham, New York, Fifth Avenue

9.4/10 Exceptional! (1,001 reviews)

Jan 16 - Jan 22

6 night stay

Chicago (MDW) to New York (JFK)

Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,733, price is now $1,892 per person
$1,892
per person
found 1 hour ago
Hospitality room was top notch!

Reviewed on Dec 8, 2025

1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

8.8/10 Excellent! (1,000 reviews)

Jan 16 - Jan 22

6 night stay

Chicago (MDW) to New York (NYC)

Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $3,212, price is now $2,174 per person
$2,174
per person
found 1 hour ago
The hotel is beautiful looking forward to visiting again.

Reviewed on Feb 21, 2023

1 Hotel Central Park
5.0-star property

1 Hotel Central Park

9/10 Wonderful! (1,001 reviews)

Jan 16 - Jan 22

6 night stay

Chicago (MDW) to New York (NYC)

Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $3,192, price is now $2,255 per person
$2,255
per person
found 1 hour ago
We have traditionally always stayed in the theater district area however more recently the area has changed. More homeless, dirtier and just not as enjoyable for us. We decided to stay more uptown in the central park area and the Orbitz site recommended the 1 Hotel Central Park. From the moment we checked in it was truly like a zen feeling and experience. Less hustle and bustle checking in, the staff was super friendly, attentive and helpful in every way from the check to the concierge. The room was modern (in a zen way), mini bar was stocked with wines, drinks and snacks. A coffee pod machine as well. The restaurant Jams, was excellent for breakfast and always packed! We HIGHLY recommend staying here and as a matter of fact tyhis will be our new go to staying in NYC.

Reviewed on Jul 13, 2025

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More About Flying To Southampton from Chicago

Route Information for Flights from Chicago to Southampton

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

Chicago to Southampton

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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.