
$39 Cheap flight deals from Chicago (CHI) to Southold (LGA)
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 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.
Airfares from $39 One Way, $79 Round Trip from Chicago to Southold
Prices starting at $79 for return flights and $39 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.
Southold economy flight packages

Hotel Riu Plaza Manhattan Times Square
Jun 5 - Jun 8
Chicago (CHI) to New York (JFK)
Reviewed on Apr 3, 2025


Southold packages with premium economy flights


INNSiDE by Meliá New York Nomad
Jun 5 - Jun 9
Chicago (ORD) to New York (JFK)
Reviewed on Apr 13, 2025

Millennium Hotel Broadway Times Square
Jun 5 - Jun 9
Chicago (ORD) to New York (JFK)
Reviewed on Apr 29, 2025
Southold first class flight packages


Renaissance New York Times Square Hotel by Marriott
Jun 8 - Jun 12
Chicago (ORD) to New York (JFK)
Reviewed on Dec 7, 2024

Residence Inn by Marriott New York Manhattan/Times Square
Jun 8 - Jun 12
Chicago (ORD) to New York (JFK)
Reviewed on Dec 27, 2024
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 | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Southold
If you are looking online for bargain Chicago to Southold flights, Orbitz is your ideal destination. We understand that vacations can be expensive and offer guaranteed low prices on our domestic and international tickets.
Orbitz Uses Cutting-Edge Mobile Tools
Orbitz may offer low cost Chicago to Southold flights but this does not mean that we skimp on giving you the latest mobile apps. You don’t have to worry about checking your flight status as we send the info for your flights from Chicago to Southold directly to your smartphone.
Fly Cheap and Earn Miles on Your Chicago to Southold Flights
Frequent flyer miles and points are great—and even better when you earn them on cheap flights from Chicago to Southold. With Orbitz, you can earn miles for your frequent flyer program on qualified flights. Enter your frequent flyer number when you book with us to get rewarded for your flight.
Orbitz Takes the Hassle Out Of Flying
We know that flying can be stressful, particularly if you are traveling with young children. That’s why we make sure you are aware of any changes or delays to your flights from Chicago to Southold via your phone or email address. We can even inform family members too.
Orbitz Flights Fit Around Your Lifestyle
Orbitz understands that you don’t necessarily want to fly at 5:00 a.m—and that sometimes you do. This is why we allow you to find the best Chicago to Southold flights at the times you want with ease.
Flights from Chicago
- Chicago to New York
- Chicago to Orlando
- Chicago to Houston
- Chicago to Phoenix
- Chicago to Los Angeles
- Chicago to London
- Chicago to Dallas
- Chicago to Washington
- Chicago to Toronto
- Chicago to Paris
- Chicago to New Orleans
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Kansas City
- Chicago to Sacramento
- Chicago to Hartford
- Chicago to Atlantic City
Top Trending
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.