$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, $69 Round Trip from Chicago to Florida Keys
Prices starting at $69 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
Kompose Boutique Hotel Miami Airport
Oct 20 - Oct 27
Chicago (CHI) to Miami (MIA)
Reviewed on Sep 17, 2025
The Retreat Collection at 1 Hotel & Homes South Beach
Nov 7 - Nov 11
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Sunset Cove Beach Resort
Oct 28 - Nov 1
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Feb 21, 2025
Florida Keys packages with premium economy flights
Oceans Edge Key West Resort, Hotel & Marina
Nov 7 - Nov 14
Chicago (ORD) to Key West (EYW)
Reviewed on Jul 12, 2025
Lighthouse Hotel - Key West Historic Inns
Nov 7 - Nov 14
Chicago (ORD) to Key West (EYW)
Reviewed on Sep 22, 2024
Winslow's Bungalows - Key West Historic Inns
Nov 7 - Nov 14
Chicago (ORD) to Key West (EYW)
Reviewed on Jul 15, 2025
Florida Keys first class flight packages
Oceans Edge Key West Resort, Hotel & Marina
Nov 7 - Nov 10
Chicago (ORD) to Key West (EYW)
Key West (EYW) to Chicago (ORD)
Reviewed on Jul 12, 2025
Lighthouse Hotel - Key West Historic Inns
Nov 7 - Nov 10
Chicago (ORD) to Key West (EYW)
Key West (EYW) to Chicago (ORD)
Reviewed on Sep 22, 2024
The Perry Hotel & Marina Key West
Nov 7 - Nov 10
Chicago (ORD) to Key West (EYW)
Key West (EYW) to Chicago (ORD)
Reviewed on Aug 12, 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, Air Canada, JAL, 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 | 1:04PM UTC |
Latest Flight Arrival | 3:28AM UTC |
Chicago to Florida Keys
Rack up your savings with low-cost flights from Chicago to Florida Keys with Orbitz On-the-Go. Orbitz On-the-Go offers mobile-only deals and cutting edge mobile tools to help you find bargain flights from Chicago to Florida Keys.
Mobile-Only Deals on Chicago to Florida Keys flights
Find guaranteed low prices on Chicago to Florida Keys flights using Orbitz On-the-Go. You can book discount domestic flights from Chicago to Florida Keys, and international tickets on Chicago to Florida Keys flights using our mobile site and apps.
Free Alerts Are No Surprise
Not only will you find cheap tickets on flights from Chicago to Florida Keys, but Orbitz free alerts will keep you up to speed on flight status, plus gate and baggage claim details. Receive instant updates via your choice of email, voice or text. Orbitz keeps you easily on task and on budget.
Share Itineraries on Flights from Chicago to Florida Keys
Are you traveling for business, pleasure or a combination of both? Keep family, friends and business contacts posted on flight and gate info. Just use MyTrips for iPhone, Android and web phones like Blackberry and Windows.
Add Smiles to Your Miles with Sales and Deals on Chicago to Florida Keys Flights
Travel planning is easy when you store your frequent flyer and loyalty program information on your Orbitz account. Then snag a low-fare air ticket on Chicago to Florida Keys flights, and you’re done. No muss, no fuss. Your miles will fly by with Orbitz On-the-Go cutting edge mobile tools and guaranteed low prices.
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 London
- Chicago to New Orleans
- Chicago to Washington
- Chicago to Rome
- Chicago to Paris
- 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 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
- Cheap Los Angeles to Cabo San Lucas flights
- Cheap New York to Orlando flights
- Cheap Toronto to Orlando flights
- Cheap Toronto to Miami flights
- Cheap Los Angeles to New York flights
- Cheap Chicago to Las Vegas flights
- Cheap New York to Los Angeles flights
- Cheap Atlanta to Las Vegas flights
- Cheap Orlando to Miami flights
- Cheap New York to Las Vegas flights
- Cheap Seattle to Las Vegas flights
- Cheap Boston to Orlando flights
- Cheap Chicago to Phoenix flights
- Cheap Vancouver to Las Vegas flights
- Cheap Portland to Las Vegas flights
- Cheap Toronto to Las Vegas flights
- Cheap Houston to Las Vegas flights
- Cheap Denver to Las Vegas flights
- Cheap New York to Miami flights
- Cheap Los Angeles to Las Vegas flights
- Cheap Minneapolis - St. Paul to Las Vegas flights
- Cheap Toronto to Los Angeles flights
- Cheap Chicago to New York flights
- Cheap New York to Atlanta flights
- Cheap Atlanta to New York flights
- Cheap Atlanta to Miami flights
- Cheap New York to London flights
- Cheap Toronto to New York flights
- Cheap Dallas to Las Vegas flights
- Cheap Detroit to Las Vegas flights
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.