Cheap Flight Deals From Chicago (CHI) to Florida Keys (MIA) Starting at $63

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 $63 One Way, $126 Round Trip from Chicago to Florida Keys

Prices starting at $126 for return flights and $63 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

EAST Miami
Private Ocean Condos at Marenas Beach
Hilton Cabana Miami Beach
Don't see what you're looking for?
See all available trips from Chicago to Florida Keys
View all trips

Florida Keys first class flight packages

Almond Tree Inn Hotel - Adults Only
Southernmost Beach Resort
The Marker Key West Harbor Resort
Don't see what you're looking for?
See all available trips from Chicago to Florida Keys
View all trips

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, SA AVIANCA, SAS, Finnair, Royal Jordanian, Iberia, ANA, Spirit Airlines, British Airways
Earliest Flight Arrival 1:09PM UTC
Latest Flight Arrival 4:21AM UTC

Chicago to Florida Keys

When you’re searching for Chicago to Florida Keys flights for your family vacation, check out the guaranteed low prices at Orbitz. If you are looking for the best prices on hotels too, you’ll be sure to find great deals to suit your budget. You’ll also benefit from the following features:

Suitable Schedules

Orbitz simplifies the process of finding and booking budget flights from Chicago to Florida Keys. Since we monitor hundreds of flight fares, you can compare several flights from a range of different airlines to find the best fares and most suitable departure and arrival times. Mix and match your departure and return flight for even more discounts and travel flexibility.

Mobile Apps

Taking a lunch break or waiting to pick up the kids? Orbitz’s cutting-edge mobile tools will help you search for cheap Chicago to Florida Keys flights anywhere you are. Get exclusive mobile deals on flights, hotels, vacation packages, and cruises too.

Flight Alerts

Orbitz won’t leave you wondering whether your flight will take off on time. We can send you free alerts about your flights from Chicago to Florida Keys to your mobile phone and email. Whether your flights from Chicago to Florida Keys are running just a few minutes to a few hours late, we will let you know.

Miles and Points

If you travel regularly, you can still earn miles and points when you book qualifying Chicago to Florida Keys flights. Enter your frequent flyer number with your reservation to see the miles rack up.

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.