$39 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 $39 One Way, $56 Round Trip from Chicago to Florida Keys
Prices starting at $56 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
Creekside Inn
Apr 10 - Apr 13
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Aug 2, 2025
President Hotel
Apr 10 - Apr 14
Chicago (CHI) to Miami (MIA)
Reviewed on Feb 20, 2026
Cavalier Hotel South Beach
Apr 10 - Apr 14
Chicago (CHI) to Miami (MIA)
Reviewed on Jan 3, 2026
Florida Keys packages with premium economy flights
Hollywood Beachside Boutique Suites
Apr 16 - Apr 19
Chicago (ORD) to Miami (MIA)
Miami (MIA) to Chicago (ORD)
Reviewed on Feb 11, 2026
Fort Lauderdale Beach Resort by Vacatia
Apr 16 - Apr 19
Chicago (ORD) to Miami (MIA)
Miami (MIA) to Chicago (ORD)
Reviewed on Feb 13, 2026
Costa Hollywood Beach Resort
Apr 16 - Apr 19
Chicago (ORD) to Miami (MIA)
Miami (MIA) to Chicago (ORD)
Reviewed on Aug 6, 2025
Florida Keys first class flight packages
Havana Cabana at Key West
Apr 16 - Apr 19
Chicago (CHI) to Key West (EYW)
Reviewed on Feb 2, 2026
The Key West Hotel
Apr 16 - Apr 19
Chicago (CHI) to Key West (EYW)
Reviewed on Jan 5, 2025
Southernmost Beach Resort and Guesthouses
Apr 16 - Apr 19
Chicago (CHI) to Key West (EYW)
Reviewed on Feb 23, 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
Great Deals on Flights From Chicago to Florida Keys
Spend more of your time and money at Florida Keys instead of sitting at your computer, searching for discount Chicago to Florida Keys flights. This is why Orbitz makes it easy for you to check out destinations, plan your trip, and book your air fare, hotel, car rental, and more in just one place. Our low price guarantee means that you get great deals on flights from Chicago to Florida Keys.
Flights That Fit Your Budget
Traveling on a budget? Not to worry if you are using Orbitz. We monitor thousands of fares to make sure we show you the best air ticket prices available for your travel dates. Besides amazing prices on Chicago to Florida Keys flights, we offer you great deals on hotels, vacation packages, and last-minute getaways for the perfect trip.
Orbitz customers can receive credit for frequent flyer miles and points. Simply provide your frequent flyer details when you book qualifying Chicago to Florida Keys flights with Orbitz.
Search for Flights from Chicago to Florida Keys on the Go
Orbitz offers free mobile apps for iPad, iPhone, and Android-based devices, so even the busiest trip-planner can research and book flights from Chicago to Florida Keys. Find cheap Chicago to Florida Keys flights, research local festivities and attractions, and book reservations while sitting in the salon. Orbitz will also update you on flight delays with free alerts sent to your mobile phone or email address, so you’re never left in the dark.
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.