$36 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 $36 One Way, $89 Round Trip from Chicago to Florida Keys
Prices starting at $89 for return flights and $36 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
Creekside Inn
Jun 1 - Jun 8
Chicago (CHI) to Miami (MIA)
Reviewed on Mar 22, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Jun 1 - Jun 8
Chicago (CHI) to Miami (MIA)
Reviewed on Feb 8, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
Jun 9 - Jun 12
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Florida Keys packages with premium economy flights
Cavalier Hotel South Beach
Jun 11 - Jun 14
Chicago (CHI) to Miami (MIA)
Reviewed on Jan 3, 2026
1 Hotel South Beach
Jun 11 - Jun 14
Chicago (CHI) to Miami (MIA)
Reviewed on Jan 17, 2026
Florida Keys first class flight packages
Hotel Colonnade Coral Gables, Autograph Collection
May 20 - May 25
Chicago (ORD) to Miami (MIA)
Reviewed on Oct 14, 2025
JW Marriott Turnberry Resort & Spa
May 20 - May 25
Chicago (ORD) to Miami (MIA)
Reviewed on Aug 24, 2025
Cadillac Hotel & Beach Club, Autograph Collection
May 20 - May 25
Chicago (ORD) to Miami (MIA)
Reviewed on Jan 19, 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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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.