$29 Cheap flight deals from Chicago (CHI) to Florida Keys (MIA)
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 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 $29 One Way, $59 Round Trip from Chicago to Florida Keys
Prices starting at $59 for return flights and $29 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
Hyatt Place Miami Airport-East
Apr 5 - Apr 10
Chicago (CHI) to Miami (MIA)
Reviewed on Feb 3, 2026
Creekside Inn
Mar 22 - Mar 26
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Aug 2, 2025
Cavalier Hotel South Beach
Apr 4 - Apr 7
Chicago (CHI) to Miami (MIA)
Reviewed on Jan 3, 2026
Florida Keys packages with premium economy flights
Crowne Plaza Hotel Fort Lauderdale Airport/Cruiseport by IHG
Apr 3 - Apr 6
Chicago (CHI) to Miami (MIA)
Reviewed on Feb 3, 2026
Flow Fort Lauderdale Hotel
Apr 3 - Apr 6
Chicago (CHI) to Miami (MIA)
Reviewed on Jan 13, 2025
Florida Keys first class flight packages
Creekside Inn
Apr 3 - Apr 10
Chicago (ORD) to Miami (MIA)
Reviewed on Aug 2, 2025
The Retreat Collection at 1 Hotel & Homes South Beach
Mar 22 - Mar 28
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
1 Hotel South Beach
Mar 22 - Mar 28
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Jan 17, 2026
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
Looking for guaranteed low prices on Chicago to Florida Keys flights? Orbitz is your source and much more. From cutting-edge mobile tools to great deals, Orbitz makes it easy to book your dream vacation.
Frequent Flyers Earn Miles
Earn frequent flyer miles or points on Orbitz flights from Chicago to Florida Keys. When booking your Chicago to Florida Keys flights, have your frequent flyer number on hand and add it where prompted. Your Orbitz account can store your number for future use, meaning you never miss out on your rewards.
Book Orbitz on the Go
With the Orbitz mobile apps for Android and iPhone, you no longer have to be sitting at your desk to book Chicago to Florida Keys flights. With a few easy clicks, you can book your flights, research hotel rooms, and check your flight status and other important flight information.
Easily Plan Your Vacation
Not only does Orbitz offer great prices on flights from Chicago to Florida Keys, but you will also find fantastic deals on hotels, cruises, and vacation activities. Never miss out on that dream trip or waste hours waiting in long lines—you can buy tickets to attraction in advance with Orbitz to guarantee admission to your favorite places.
Best Deals At Your Fingertips
Orbitz combines low prices on Chicago to Florida Keys flights with discounts on quality hotels. Using Orbitz’s Display Matrix, you can see all your options and savings easily. With our low price guarantee, you know you have the best deals at your fingertips.
Flights from Chicago
- Chicago to Los Angeles
- Chicago to New York
- Chicago to Orlando
- Chicago to Toronto
- Chicago to Houston
- Chicago to London
- Chicago to Detroit
- Chicago to Phoenix
- Chicago to Rome
- Chicago to Cleveland
- Chicago to Dallas
- Chicago to New Orleans
- Chicago to San Francisco
- Chicago to Washington
- Chicago to Paris
- Chicago to Sao Paulo
- Chicago to Sacramento
- Chicago to Killeen
- Chicago to Kansas City
- Chicago to Montreal
- Flights to Key West
- Flights to Melbourne
- Flights to Marathon
- Flights to Bradenton
- Flights to Boca Raton
- Flights to Bonita Springs
- Flights to Cape Canaveral
- Flights to Cape Coral
- Flights to Cocoa Beach
- Flights to Pensacola Beach
- Flights to Siesta Key
- Flights to Destin
- Flights to Fort Myers Beach
- Flights to Fort Pierce
- Flights to Kissimmee
- Flights to Panama City Beach
- Flights to Florida City
- Flights to Key Largo
- Flights to Marco Island
- Flights to Miami Beach
- Flights to Punta Gorda
- Flights to Pompano Beach
- Flights to Sanibel
- Flights to St Pete Beach
- Flights to Sanford
- Flights to Titusville
- Flights to Port Saint Lucie
- Flights to Clearwater Beach
- Flights to Islamorada
- Flights to Anna Maria
- Flights to Miami
- Flights to Orlando
- Flights to St Petersburg Clearwater
- Flights to Fort Lauderdale
- Flights to Palm Beach West Palm Beach
- Flights to Sarasota
- Flights to Naples
- Flights to Fort Myers
- Flights to Tampa
- Flights to Jacksonville
- Flights to Panama City
- Flights to Pensacola
- Flights to Fort Walton Beach Destin
- Flights to Vero Beach
- Flights to Florida Keys
- Flights to Daytona Beach
- Flights to St Augustine
- Flights to Gainesville
- Flights to Tallahassee
- Flights to Leesburg
- Flights to Ocala
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.