$28 Cheap flight deals from Chicago (CHI) to Florida Keys (MIA)
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This Weekend's Flight Deals from Chicago to Florida Keys
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 $28 One Way, $57 Round Trip from Chicago to Florida Keys
Prices starting at $57 for return flights and $28 for one-way flights to Florida Keys were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Florida Keys economy flight packages
Creekside Inn
May 21 - May 25
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Mar 22, 2026
Casablanca Miami Beach
May 19 - May 24
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Apr 8, 2025
Florida Keys packages with premium economy flights
Ramada by Wyndham Miami Springs/Miami International Airport
May 8 - May 11
Chicago (ORD) to Miami (MIA)
Reviewed on Mar 12, 2026
The St. Regis Bal Harbour Resort
May 8 - May 11
Chicago (ORD) to Miami (MIA)
Reviewed on Nov 3, 2025
Sleep Inn Miami International Airport
May 8 - May 11
Chicago (ORD) to Miami (MIA)
Reviewed on Feb 1, 2026
Florida Keys first class flight packages
Cavalier Hotel South Beach
May 15 - May 18
Chicago (ORD) to Miami (MIA)
Reviewed on Jan 3, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
May 15 - May 18
Chicago (ORD) to Miami (MIA)
More About Flying To Florida Keys from Chicago
Route Information for Flights from Chicago to Florida Keys
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | MIA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Florida Keys
When you’re ready to take your next trip, get the most affordable prices on flights from Chicago to Florida Keys 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 Florida Keys, 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 Florida Keys Flights
Orbitz features both an Android app and an iPhone app to give you the lowest prices for Chicago to Florida Keys 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 Florida Keys, 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 Florida Keys flights automatically without the annoying hassle of having to look them up.
Flights from Chicago
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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.