$137 Cheap flight deals from Chicago (CHI) to Rockland Key (EYW)
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 Rockland Key
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 $137 One Way, $269 Round Trip from Chicago to Rockland Key
Prices starting at $269 for return flights and $137 for one-way flights to Rockland Key were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Rockland Key economy flight packages
The Grand Guesthouse
Oct 1 - Oct 6
Chicago (ORD) to Key West (EYW)
Reviewed on Feb 28, 2025
More About Flying To Rockland Key from Chicago
Route Information for Flights from Chicago to Rockland Key
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | EYW |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Rockland Key
When you’re ready to take your next trip, get the most affordable prices on flights from Chicago to Rockland Key with Orbitz! The guaranteed low prices and cutting-edge mobile tools on Orbits make it easy for you to plan your next great vacation.
Keep Up With Sudden Flight Changes
As any traveler knows, air travel can suddenly be temporarily halted due to service disruptions. Along with offering the best fares for flights from Chicago to Rockland Key, Orbitz also offers free mobile phone and email alerts that help you keep up with sudden changes to your flight plans. Choose from email, text, or voice message alerts.
Get Great Prices for Chicago to Rockland Key Flights
Orbitz features both an Android app and an iPhone app to give you the lowest prices for Chicago to Rockland Key flights. Use these mobile apps to get updates on your flight, the details of your itinerary, and to learn about available hotel deals in the area.
Fly for Less and Earn Miles
Did you know you can earn miles and points for your frequent flyer program with Orbitz? To do this with specific flights from Chicago to Rockland Key, enter your frequent flyer account number when you book your ticket online. For even more convenience, keep a record of your loyalty travel program numbers directly with Orbitz by storing them in your account profile. This way, you can add your account numbers to your next reservation for Chicago to Rockland Key flights automatically without the annoying hassle of having to look them up.
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
Rockland Key Airports
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.