$30 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.

Sun, Mar 2 - Wed, Mar 12
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$103 Roundtrip, just found
$103
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Mar 2 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Wed, Mar 12, priced at $103 just found
Sat, Mar 1 - Wed, Mar 5
MDW
Midway Intl.
LGA
LaGuardia
$111 Roundtrip, found 4 days ago
$111
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Mar 1 from Midway Intl. to LaGuardia, returning Wed, Mar 5, priced at $111 found 4 days ago
Sat, Mar 1 - Wed, Mar 5
MDW
Midway Intl.
JFK
John F. Kennedy Intl.
$127 Roundtrip, found 2 hours ago
$127
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Mar 1 from Midway Intl. to John F. Kennedy Intl., returning Wed, Mar 5, priced at $127 found 2 hours ago
Sat, Mar 1 - Wed, Mar 5
ORD
O'Hare Intl.
LGA
LaGuardia
$134 Roundtrip, found 1 hour ago
$134
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Mar 1 from O'Hare Intl. to LaGuardia, returning Wed, Mar 5, priced at $134 found 1 hour ago

Airfares from $30 One Way, $58 Round Trip from Chicago to Southold

Prices starting at $58 for return flights and $30 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, Apr 29 - Wed, Apr 30
ORD
Chicago
LGA
New York
$58 Roundtrip, found 3 days ago
$58
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Apr 29 from Chicago to New York, returning Wed, Apr 30, priced at $58 found 3 days ago
Tue, Apr 1 - Wed, Apr 2
ORD
Chicago
EWR
New York
$61 Roundtrip, found 2 hours ago
$61
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Apr 1 from Chicago to New York, returning Wed, Apr 2, priced at $61 found 2 hours ago
Tue, Mar 11 - Wed, Mar 26
MDW
Chicago
LGA
New York
$110 Roundtrip, found 11 hours ago
$110
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Mar 11 from Chicago to New York, returning Wed, Mar 26, priced at $110 found 11 hours ago
Tue, May 27 - Tue, Jun 3
MDW
Chicago
JFK
New York
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, May 27 from Chicago to New York, returning Tue, Jun 3, priced at $110 found 2 days ago
Wed, Mar 19 - Tue, Apr 1
ORD
Chicago
EWR
New York
$110 Roundtrip, just found
$110
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Mar 19 from Chicago to New York, returning Tue, Apr 1, priced at $110 just found

Southold economy flight packages

Price found within the past 48 hours. Click for updated prices.
The William Vale
5.0-star property

The William Vale

8.6/10 Excellent! (1,003 reviews)

Mar 31 - Apr 2

2 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
per person
found 2 hours 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! (1,002 reviews)

Mar 31 - Apr 2

2 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 2 hours ago
The hotel is beautiful looking forward to visiting again.

Reviewed on Feb 21, 2023

Night Hotel Broadway
2.5-star property

Night Hotel Broadway

6.8/10 (1,834 reviews)

Mar 28 - Apr 1

4 night stay

Chicago (CHI) to New York (JFK)

Frontier Airlines • Non-stop • Coach

New York (JFK) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
per person
found 8 hours ago
Simple but exactly what I needed for a quick business trip close to Columbia. Clean, safe, comfortable. Very pleased and will stay again.

Reviewed on Nov 9, 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
Delta Air Lines, Gol, El Al, SAS, Iberia, Korean Air, WestJet, Singapore Airlines, Gulf Air, American Airlines, Qatar Airways, KLM, Air Europa, Air France, China Airlines, Kenya Airways, Alaska Airlines, Royal Air Maroc, Etihad Airways, JetBlue, LATAM Airlines, Finnair, ITA Airways, TAP Air Portugal, Virgin Atlantic, British Airways
Earliest Flight Arrival
3:27PM UTC
Latest Flight Arrival
3:02AM UTC

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Orbitz has the best prices available on flights from Chicago to Southold. Take advantage of our low fare sales and discounts and begin to plan your next trip. We also give you great savings on hotels, car rentals, and vacation packages.

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.