$76 Cheap flight deals from Chicago (CHI) to Florida Keys (MIA)
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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 $76 One Way, $162 Round Trip from Chicago to Florida Keys
Prices starting at $162 for return flights and $76 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
The Retreat Collection at 1 Hotel & Homes South Beach
Oct 9 - Oct 12
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Jun 22, 2016
EAST Miami Residences
Oct 18 - Oct 23
Chicago (CHI) to Miami (MIA)
Reviewed on Aug 25, 2026
Florida Keys first class flight packages
Hotel Riu Plaza Miami Beach
Oct 9 - Oct 11
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Aug 29, 2026
1 Hotel South Beach
Oct 9 - Oct 11
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Nobu Hotel Miami Beach
Oct 9 - Oct 11
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Aug 29, 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
Orbitz is the number one travel site for finding guaranteed low prices on Chicago to Florida Keys flights. Not only do we have discount tickets on domestic and international tickets but our cutting-edge mobile tools keep you informed on the go.
Find Low Prices in One Place
Booking a trip from Chicago to Florida Keys has never been easier. Not only will you find great deals on flights, we offer bargains on cruises, car rentals, top-notch hotels, and more. You can also research and add local activities in Florida Keys to your flight or hotel reservation to keep the kids happy and active.
Flight Booking, Alerts, and More on Your Mobile Device
Use our mobile app for your iPhone, iPad, or Android phone—or our mobile website m.orbitz.com—to find bargains on flights from Chicago to Florida Keys wherever you are. Book your cheap Chicago to Florida Keys flights and a hotel room too—even at the last minute. Orbitz also makes your life easier with free alerts that are sent to your mobile phone or email about delays to your upcoming flights from Chicago to Florida Keys.
Don’t Miss out on Miles
Accumulate frequent flyer miles or points on your Chicago to Florida Keys flights. It’s as simple as entering your frequent flyer number when you’re making your flight reservation on Orbitz to rack up miles on qualified flights from Chicago to Florida Keys. You can save your frequent flyer numbers in your Orbitz account to save time during your next flight booking.
Flights from Chicago
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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.