$75 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 $75 One Way, $152 Round Trip from Chicago to Florida Keys
Prices starting at $152 for return flights and $75 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
Eden Roc Miami Beach
Oct 9 - Oct 14
Chicago (CHI) to Miami (MIA)
Reviewed on Aug 18, 2026
Southernmost House - Adult Exclusive
Oct 11 - Oct 17
Chicago (CHI) to Key West (EYW)
Reviewed on Aug 16, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
Sep 18 - Sep 21
Chicago (ORD) to Miami (MIA)
Reviewed on Jun 22, 2016
Florida Keys first class flight packages
Fontainebleau Miami Beach
Sep 22 - Sep 29
Chicago (ORD) to Miami (MIA)
Reviewed on Aug 18, 2026
1 Hotel South Beach
Sep 22 - Sep 29
Chicago (ORD) to Miami (MIA)
Reviewed on Aug 16, 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
Book your trip through Orbitz for the best deals on Chicago to Florida Keys flights. With our cutting-edge mobile tools, getting fantastic savings on international or domestic flights or updates on your flight status has never been easier. Find your low-priced flights from Chicago to Florida Keys today with Orbitz.
Frequent Flyer Rewards
If you are a member of a frequent flyer program, Orbitz will ensure you get points or miles for your qualifying Chicago to Florida Keys flights. Just provide your frequent flyer number or your loyalty program number when booking your flight online with Orbtiz.com.
Flight Deals on the Go
Never miss out on great savings! Get fantastic deals on flights from Chicago to Florida Keys on your mobile device with our apps for iPhone, Android, and iPad, or use your mobile Web browser to access m.orbitz.com. Find big discounts on the hotels you want to stay at to go along with your Chicago to Florida Keys flights. The app even gives you information for baggage claim and other important flight details.
Free Flight Alerts
With Orbitz, not do you get amazing low-cost deals on Chicago to Florida Keys flights, but we can send you flight alerts to your mobile phone or email. Instantly learn about delays to your flights from Chicago to Florida Keys, so you can plan ahead and make different travel arrangements if you need to.
Guaranteed low prices for Chicago to Florida Keys flights makes Orbitz the perfect online budget travel source.
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 Toronto
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Sacramento
- Chicago to Montreal
- 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.