$89 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 $89 One Way, $177 Round Trip from Chicago to Florida Keys
Prices starting at $177 for return flights and $89 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
The Penguin Hotel
Dec 2 - Dec 5
Chicago (CHI) to Miami (MIA)
Reviewed on Oct 18, 2026
Avi Lux Stay
Nov 25 - Nov 29
Chicago (CHI) to Miami (MIA)
Reviewed on Aug 28, 2025
Florida Keys first class flight packages
Orchid Key Inn - Adults Only
Dec 7 - Dec 11
Chicago (ORD) to Key West (EYW)
Reviewed on Oct 16, 2026
The Key West Hotel
Dec 7 - Dec 11
Chicago (ORD) to Key West (EYW)
Reviewed on Oct 6, 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
The best fares for Chicago to Florida Keys flights are always found on Orbitz. With superior discounts and the latest innovations in mobile access, your ideal trip starts with Orbitz.
The Easy Way to Plan Travel Cheaply
We provide access to many low-cost vacation packages and travelers can mix and match airlines when scheduling their flights for the best prices and flight times. Finding cheap tickets on flights from Chicago to Florida Keys is easy when you make Orbitz your #1 travel planner.
Book Chicago to Florida Keys Flights With Mobile Apps
Our iPhone and Android mobile apps can be used to compare and book flights from Chicago to Florida Keys. These apps are perfect for checking the status of flights, gate and baggage claims details, car rental rates, and for receiving alerts on special savings that are exclusive to mobile users. Mobile app users can even score great rates when booking hotel rooms. You can compare hotels, virtually view photo galleries, and check out user reviews using the app, as well as find out which ones are closest to you.
Orbitz also offers free travel updates that are sent to your email or mobile phone that notifies you of booking changes, disruptions in service, or delayed flights.
Increase Your Rewards While Enjoying Super Low Rates
Boost your points or miles for your frequent flyer program on certain Chicago to Florida Keys flights. Simply provide your frequent flyer information when booking flights from Chicago to Florida Keys with Orbitz and get both a low fare and travel rewards. You can enter this information in your Orbitz account profile for easy remembering in future bookings.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to New Orleans
- Chicago to Washington
- Chicago to London
- Chicago to Paris
- Chicago to Rome
- Chicago to Toronto
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Atlantic City
- Chicago to Hartford
- 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.