$44 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 $44 One Way, $108 Round Trip from Chicago to Florida Keys
Prices starting at $108 for return flights and $44 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
Flow Miami Hotel
Jul 21 - Jul 28
Chicago (CHI) to Miami (MIA)
Reviewed on Apr 6, 2025
Solé Miami, A Noble House Resort
Jul 23 - Jul 31
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on May 19, 2025
Florida Keys packages with premium economy flights
La Quinta Inn & Suites by Wyndham Miami Airport East
Jul 25 - Jul 28
Chicago (ORD) to Miami (MIA)
Reviewed on May 20, 2025
Biltmore Hotel - Miami - Coral Gables
Jul 25 - Jul 28
Chicago (ORD) to Miami (MIA)
Reviewed on Oct 23, 2023
Florida Keys first class flight packages
Winslow's Bungalows - Key West Historic Inns
Jul 11 - Jul 14
Chicago (CHI) to Key West (EYW)
Reviewed on Mar 6, 2025
Lighthouse Hotel - Key West Historic Inns
Jul 11 - Jul 14
Chicago (CHI) to Key West (EYW)
Reviewed on Sep 22, 2024
Orchid Key Inn - Adults Only
Jul 11 - Jul 14
Chicago (CHI) to Key West (EYW)
Reviewed on Jan 20, 2025
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 | 1199 mi |
Direct Flight Airlines | American Airlines, Qatar Airways, JAL, Air Canada, Aer Lingus, Copa Airlines, Air New Zealand, United Airlines, Gol, Alaska Airlines, Royal Air Maroc, Avianca, Royal Jordanian, Spirit Airlines, British Airways |
Earliest Flight Arrival | 1:07PM UTC |
Latest Flight Arrival | 3:15AM UTC |
Chicago to Florida Keys
Orbitz has your best deals on Chicago to Florida Keys flights. From guaranteed low prices to cutting-edge mobile tools, the perfect trip begins on Orbitz.
Get Orbitz On the Go for Flights from Chicago to Florida Keys
Use our mobile apps for Android and iPhone to find the best price on flights from Chicago to Florida Keys. Check your flight status, gate and baggage claim details, and book exclusive mobile deals on hotels — even on the same day.
Rack Up Miles While Flying for Cheaper
Earn miles or points toward your frequent flyer program on select Chicago to Florida Keys flights. When you book your flight on Orbitz, simply add your qualifying frequent flyer number where prompted. You can also store your airline frequent flyer or loyalty program numbers in your Orbitz account profile to automatically add them to your future reservations.
Worry Less With Flight Alerts
Orbitz is the best source for booking flights from Chicago to Florida Keys. But we also keep you updated about flight delays, booking changes, or service disruptions with free alerts. Get alerts on Chicago to Florida Keys flights sent to your email or via voice or text to your mobile phone. We can also send the alerts to up to 6 other email addresses or phone numbers, which is helpful if you are being picked up at the airport.
Budget Travel Planning Made Easy
It's easy to find discount air tickets for flights from Chicago to Florida Keys on Orbitz. Mix and match airlines for your departing and your returning flights to find the lowest fares and the best schedule.
Flights from Chicago
- Chicago to New York
- Chicago to Orlando
- Chicago to Houston
- Chicago to Phoenix
- Chicago to Los Angeles
- Chicago to London
- Chicago to Dallas
- Chicago to Washington
- Chicago to Toronto
- Chicago to Paris
- Chicago to New Orleans
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Kansas City
- Chicago to Sacramento
- 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
Top Trending
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.