$91 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 $91 One Way, $177 Round Trip from Chicago to Florida Keys
Prices starting at $177 for return flights and $91 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
Private Oasis at Arya
Oct 23 - Oct 26
Chicago (CHI) to Miami (MIA)
Reviewed on Sep 23, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
Nov 5 - Nov 8
Chicago (CHI) to Miami (MIA)
Reviewed on Jun 22, 2016
1 Hotel South Beach
Nov 1 - Nov 6
Chicago (CHI) to Miami (MIA)
Reviewed on Sep 23, 2026
Florida Keys first class flight packages
President Hotel
Nov 5 - Nov 9
Chicago (ORD) to Miami (MIA)
Miami (MIA) to Chicago (ORD)
Reviewed on Sep 23, 2026
1 Hotel South Beach
Nov 5 - Nov 9
Chicago (ORD) to Miami (MIA)
Miami (MIA) to Chicago (ORD)
Reviewed on Sep 23, 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
If you are looking to find the best deals on Chicago to Florida Keys flights, look no further than Orbitz. Orbitz offers guaranteed low prices as well as cutting-edge mobile tools to help you book cheap flights from Chicago to Florida Keys.
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Get Miles for Your Flights From Chicago to Florida Keys
It’s easy to earn points or miles for your frequent flyer or airline loyalty program on qualifying Chicago to Florida Keys flights with Orbitz. You can add your frequent flyer number to your online flight booking, and even store your numbers in your Orbitz account profile so they automatically get added the next time you book a flight.
Stay Informed While You Travel
Orbitz keeps you updated on information that’s relevant to your flights from Chicago to Florida Keys. We can send you and six of your personal contacts free travel alerts via SMS text, voicemail, or email, so you instantly know about flight delays or changes.
Keep More Money in Your Pocket With Discount Flights
Orbitz looks for the best deals on Chicago to Florida Keys flights for you. Mix and match airlines for your departing and return flights to fit your travel schedule and budget.
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.