$39 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 $39 One Way, $77 Round Trip from Chicago to Florida Keys
Prices starting at $77 for return flights and $39 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
Cavalier Hotel South Beach
Nov 7 - Nov 10
Chicago (CHI) to Miami (MIA)
Reviewed on Apr 28, 2025
YVE Hotel Miami
Nov 1 - Nov 8
Chicago (CHI) to Miami (MIA)
Reviewed on May 8, 2025
Florida Keys first class flight packages
Park Central South Beach
Nov 14 - Nov 16
Chicago (ORD) to Miami (MIA)
Reviewed on Aug 30, 2025
1 Hotel South Beach
Nov 14 - Nov 16
Chicago (ORD) to Miami (MIA)
Reviewed on Jun 10, 2025
Mondrian South Beach
Nov 14 - Nov 16
Chicago (ORD) to Miami (MIA)
Reviewed on Apr 26, 2025
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
It has never been easier to find cheap Chicago to Florida Keys flights. Orbitz has some of the best deals around to save you more money on your flight, hotel, and vacation package for the trip you have been waiting for.
Plan Your Chicago to Florida Keys Flights on the Go
Orbitz offers cutting-edge mobile tools that let you search and book flights anywhere. All you need is a smartphone or mobile device to find discounts on flights from Chicago to Florida Keys. Use the app to check to make sure your flight is on time or book a last-minute cheap hotel room.
Get the Best Deals on Chicago to Florida Keys Flights
Finding great deals on flights from Chicago to Florida Keys is a snap with Orbitz. With our guaranteed low prices, you don’t have to worry if you are getting the best prices on air tickets, hotels, and cruises. And with all that money you saved, you can enjoy your Florida Keys vacation even more.
Pile Up Miles With Discount Air Tickets
Not only can you find great bargains on Chicago to Florida Keys flights, but you can rack up frequent flyer miles on the flights too. Enter your frequent flyer number on qualified flights when booking for Orbitz to see the miles pile up in your account.
Flight Alerts Keep You Informed
Stay on top of the latest updates for flights from Chicago to Florida Keys. We send you free email and mobile alerts to keep you informed about delays to Chicago to Florida Keys flights.
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.