$29 Cheap flight deals from Chicago (CHI) to Islamorada (MIA)
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This Weekend's Flight Deals from Chicago to Islamorada
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 $29 One Way, $59 Round Trip from Chicago to Islamorada
Prices starting at $59 for return flights and $29 for one-way flights to Islamorada were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Islamorada economy flight packages
Solé Miami, A Noble House Resort
Feb 15 - Feb 19
Chicago (CHI) to Miami (MIA)
Reviewed on Dec 27, 2025
Cavalier Hotel South Beach
Feb 15 - Feb 19
Chicago (CHI) to Miami (MIA)
Reviewed on Jan 3, 2026
Islamorada packages with premium economy flights
Cavalier Hotel South Beach
Feb 13 - Feb 15
Chicago (ORD) to Miami (MIA)
Miami (MIA) to Chicago (ORD)
Reviewed on Jan 3, 2026
1 Hotel South Beach
Feb 26 - Mar 1
Chicago (CHI) to Miami (MIA)
Reviewed on Jun 10, 2025
Islamorada first class flight packages
Southernmost Beach Resort and Guesthouses
Mar 5 - Mar 8
Chicago (ORD) to Key West (EYW)
Reviewed on Nov 1, 2025
The Key West Hotel
Mar 5 - Mar 8
Chicago (ORD) to Key West (EYW)
Reviewed on Jan 5, 2025
Oceans Edge Key West Resort, Hotel & Marina
Mar 5 - Mar 8
Chicago (ORD) to Key West (EYW)
Reviewed on Dec 28, 2025
More About Flying To Islamorada from Chicago
Route Information for Flights from Chicago to Islamorada
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | MIA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Islamorada
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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.