$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

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
1 Hotel Brooklyn Bridge
The Fifth Avenue Hotel
Don't see what you're looking for?
See all available trips from Chicago to Southold
View all trips

Southold packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Hyatt Grand Central New York
INNSiDE by Meliá New York Nomad
Millennium Hotel Broadway Times Square
Don't see what you're looking for?
See all available trips from Chicago to Southold
View all trips

Southold first class flight packages

Price found within the past 48 hours. Click for updated prices.
Moxy NYC Downtown
Renaissance New York Times Square Hotel by Marriott
Residence Inn by Marriott New York Manhattan/Times Square
Don't see what you're looking for?
See all available trips from Chicago to Southold
View all trips

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.

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.