$25 Cheap flight deals from Chicago (CHI) to Windley Key (MIA)
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This Weekend's Flight Deals from Chicago to Windley Key
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 $25 One Way, $50 Round Trip from Chicago to Windley Key
Prices starting at $50 for return flights and $25 for one-way flights to Windley Key were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Windley Key economy flight packages
President Hotel
Mar 11 - Mar 14
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Nov 21, 2025
Creekside Inn
Mar 7 - Mar 14
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Aug 2, 2025
Windley Key packages with premium economy flights
Fontainebleau Miami Beach
Mar 22 - Mar 25
Chicago (ORD) to Miami (MIA)
Miami (MIA) to Chicago (ORD)
Reviewed on Jan 28, 2026
1 Hotel South Beach
Mar 22 - Mar 25
Chicago (ORD) to Miami (MIA)
Miami (MIA) to Chicago (ORD)
Reviewed on Jan 17, 2026
The Shelborne By Proper, a Member of Design Hotels
Mar 22 - Mar 25
Chicago (ORD) to Miami (MIA)
Miami (MIA) to Chicago (ORD)
Windley Key first class flight packages
President Hotel
Mar 10 - Mar 17
Chicago (CHI) to Miami (MIA)
Reviewed on Nov 21, 2025
Park Central South Beach
Mar 10 - Mar 17
Chicago (CHI) to Miami (MIA)
Reviewed on Dec 23, 2025
Cavalier Hotel South Beach
Mar 10 - Mar 17
Chicago (CHI) to Miami (MIA)
Reviewed on Jan 3, 2026
More About Flying To Windley Key from Chicago
Route Information for Flights from Chicago to Windley Key
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | MIA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Windley Key
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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.