$88 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 $88 One Way, $175 Round Trip from Chicago to Florida Keys
Prices starting at $175 for return flights and $88 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
Sep 18 - Sep 22
Chicago (CHI) to Miami (MIA)
Reviewed on Jun 22, 2016
Nobu Hotel Miami Beach
Sep 29 - Oct 3
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Florida Keys first class flight packages
Coconut Beach Resort
Sep 17 - Sep 22
Chicago (CHI) to Key West (EYW)
Reviewed on Aug 8, 2026
Pier House Resort & Spa
Sep 17 - Sep 22
Chicago (CHI) to Key West (EYW)
Reviewed on Aug 9, 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
For the best travel experience from Chicago to Florida Keys domestic and international travelers everywhere choose Orbitz for guaranteed low prices and cutting-edge mobile tools.
Convenient Low-Cost Travel
Orbitz makes it simple to book discount flights from Chicago to {destination.name} without compromising your schedule. You can always find deals on domestic flights from a location near you. You may find the best deals to fit your schedule by mixing and matching airlines to get you from Chicago to Florida Keys.
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You can access Orbitz anywhere at anytime for travel from Chicago to Florida Keys using the latest technology. Via your mobile phone you can track any changes to your flight status, gate and baggage claim details, and with Orbitz’s full-service mobile apps for iPhone and Android you can view these trip details anytime anywhere. You can also get fare alerts and travel updates to keep you informed of the cheapest flights from Chicago to Florida Keys.
Earn Rewards on Your Chicago to Florida Keys Flights
At Orbitz you can benefit from low cost travel and have your loyalty rewarded on certain types of Chicago to Florida Keys flights. All you need to do is enter you frequent flyer number when booking and rack up your rewards through Orbitz online on the Traveler Information page for use on future flights. You can even add your frequent flyer number to an existing reservation to start the ball rolling.
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.