$86 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 $86 One Way, $171 Round Trip from Chicago to Florida Keys
Prices starting at $171 for return flights and $86 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
Hotel Riu Plaza Miami Beach
Jul 18 - Jul 22
Chicago (CHI) to Miami (MIA)
Reviewed on Jan 19, 2026
Casablanca Miami Beach
Aug 8 - Aug 12
Chicago (CHI) to Miami (MIA)
Reviewed on Apr 8, 2025
EAST Miami Residences
Aug 11 - Aug 16
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Nov 29, 2025
Florida Keys packages with premium economy flights
The Sunny
Aug 3 - Aug 7
Chicago (CHI) to Miami (MIA)
Reviewed on Apr 8, 2026
W South Beach
Aug 3 - Aug 7
Chicago (CHI) to Miami (MIA)
Reviewed on Aug 25, 2025
Miami International Airport Hotel
Aug 3 - Aug 7
Chicago (CHI) to Miami (MIA)
Reviewed on Jun 10, 2026
Florida Keys first class flight packages
Hyatt Vacation Club at Sunset Harbor, Key West
Jul 31 - Aug 4
Chicago (ORD) to Key West (EYW)
Reviewed on Dec 1, 2024
The Key West Hotel
Jul 31 - Aug 4
Chicago (ORD) to Key West (EYW)
Reviewed on Apr 2, 2026
Hyatt Vacation Club at Beach House, Key West
Jul 31 - Aug 4
Chicago (ORD) to Key West (EYW)
Reviewed on May 6, 2026
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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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.