$44 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 $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
Barcelona Studios Guesthouse
Oct 30 - Nov 4
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Apr 13, 2025
Park Central South Beach
Oct 30 - Nov 3
Chicago (CHI) to Miami (MIA)
Reviewed on Aug 30, 2025
Cavalier Hotel South Beach
Nov 1 - Nov 6
Chicago (CHI) to Miami (MIA)
Reviewed on Apr 28, 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
Hyatt Vacation Club at Windward Pointe, Key West
Oct 26 - Nov 1
Chicago (ORD) to Key West (EYW)
Reviewed on Jun 3, 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
Bishop Hotel Key West
Oct 26 - Nov 1
Chicago (ORD) to Key West (EYW)
Reviewed on May 14, 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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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.