
$34 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 $34 One Way, $65 Round Trip from Chicago to Islamorada
Prices starting at $65 for return flights and $34 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

Creekside Inn
Feb 27 - Mar 2
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Aug 2, 2025

Cavalier Hotel South Beach
Mar 20 - Mar 24
Chicago (CHI) to Miami (MIA)
Reviewed on Jan 3, 2026

Casablanca Miami Beach
Mar 20 - Mar 24
Chicago (CHI) to Miami (MIA)
Reviewed on Apr 8, 2025
Islamorada first class flight packages

The Key West Hotel
Mar 12 - Mar 17
Chicago (CHI) to Key West (EYW)
Reviewed on Jan 5, 2025

Isla Bella Beach Resort & Spa
Mar 11 - Mar 18
Chicago (ORD) to Miami (MIA)
Reviewed on Dec 18, 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.


