$102 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 $102 One Way, $201 Round Trip from Chicago to Florida Keys
Prices starting at $201 for return flights and $102 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
Fort Lauderdale Beach Resort by Vacatia
Jul 18 - Jul 25
Chicago (CHI) to Miami (MIA)
Reviewed on May 16, 2026
Andaz Miami Beach Resort & Spa
Jul 21 - Jul 28
Chicago (CHI) to Miami (MIA)
Reviewed on Mar 26, 2026
Cavalier Hotel South Beach
Jul 16 - Jul 19
Chicago (CHI) to Miami (MIA)
Reviewed on Jan 3, 2026
Florida Keys packages with premium economy flights
Riverside Hotel
Jul 16 - Jul 19
Chicago (MDW) to Miami (MIA)
Reviewed on May 24, 2026
AC Hotel by Marriott Fort Lauderdale Beach
Jul 16 - Jul 19
Chicago (MDW) to Miami (MIA)
Reviewed on Apr 12, 2026
The Atlantic Hotel & Spa
Jul 16 - Jul 19
Chicago (MDW) to Miami (MIA)
Reviewed on Mar 18, 2026
Florida Keys business class flight packages
Lime Tree Bay Resort
Jul 7 - Jul 13
Chicago (CHI) to Miami (MIA)
Reviewed on Feb 6, 2026
Villas At Hawks Cay Resort
Jul 7 - Jul 13
Chicago (CHI) to Miami (MIA)
Reviewed on May 16, 2026
Seascape Resort & Marina
Jul 7 - Jul 13
Chicago (CHI) to Miami (MIA)
Reviewed on Dec 10, 2025
Florida Keys first class flight packages
1 Hotel South Beach
Jul 23 - Jul 29
Chicago (ORD) to Miami (MIA)
Reviewed on Jan 17, 2026
Andaz Miami Beach Resort & Spa
Jul 23 - Jul 29
Chicago (ORD) to Miami (MIA)
Reviewed on Mar 26, 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
For guaranteed low prices on flights from Chicago to Florida Keys, search no further than Orbitz. Planning the perfect trip is simple with Orbitz; our range of bargain holiday packages and cutting edge mobile tools makes it quick and easy.
Mobile Movers
Never miss out on bargain prices on Chicago to Florida Keys flights with free mobile apps for Android and iPhone. On the road? Not a problem – just use m.orbitz.com in your mobile browser to book flights from Chicago to Florida Keys or check the latest details of your flights.
All-in-One
With Orbitz’s Display Matrix, it is so easy to book your perfect vacation package. Just add in flights from Chicago to Florida Keys, decide if you want hotels and car rental included and click the button! Orbitz’s Display Matrix clearly shows all the deals and great savings available, including extra discounts, such as free nights.
Cheap Flights Equals Extra Miles
Enjoy great deals on Chicago to Florida Keys flights and rack up those air miles at the same time! With Orbitz you just add in your frequent flyer number when asked and your qualifying miles are instant. Store your number to your account profile and next time you book your miles will be automatically added.
Safeguard with our Low Price Guarantee
Feel confident when you book your Chicago to Florida Keys flights, a great hotel or a full vacation package that you are getting the best deal around. Orbitz’s low price guarantee assures you of peace of mind.
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 London
- Chicago to Washington
- Chicago to Paris
- Chicago to Toronto
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
- 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.