$30 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 $30 One Way, $58 Round Trip from Chicago to Florida Keys
Prices starting at $58 for return flights and $30 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
Pelican Hotel
Jan 28 - Jan 31
Chicago (CHI) to Miami (MIA)
Reviewed on Aug 11, 2025
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
Jan 21 - Jan 27
Chicago (ORD) to Miami (MIA)
Reviewed on Dec 14, 2025
Florida Keys packages with premium economy flights
Southernmost Beach Resort and Guesthouses
Jan 28 - Feb 1
Rockford (RFD) to Key West (EYW)
Reviewed on Nov 1, 2025
The Key West Hotel
Jan 28 - Feb 1
Rockford (RFD) to Key West (EYW)
Reviewed on Jan 5, 2025
Lighthouse Hotel - Key West Historic Inns
Jan 28 - Feb 1
Rockford (RFD) to Key West (EYW)
Reviewed on Sep 22, 2024
Florida Keys first class flight packages
Southernmost Beach Resort and Guesthouses
Feb 5 - Feb 11
Chicago (CHI) to Key West (EYW)
Reviewed on Nov 1, 2025
The Key West Hotel
Feb 5 - Feb 11
Chicago (CHI) to Key West (EYW)
Reviewed on Jan 5, 2025
Oceans Edge Key West Resort, Hotel & Marina
Feb 5 - Feb 11
Chicago (CHI) to Key West (EYW)
Reviewed on Sep 21, 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 | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Florida Keys
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Flights from Chicago
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- Flights to Key West
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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.