$101 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 $101 One Way, $201 Round Trip from Chicago to Florida Keys
Prices starting at $201 for return flights and $101 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
Florida Keys first class flight packages
Hyatt Vacation Club at Windward Pointe, Key West
Jul 8 - Jul 13
Chicago (CHI) to Key West (EYW)
Reviewed on Apr 26, 2026
The Key West Hotel
Jul 8 - Jul 13
Chicago (CHI) to Key West (EYW)
Reviewed on Apr 2, 2026
Hyatt Vacation Club at Beach House, Key West
Jul 8 - Jul 13
Chicago (CHI) 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
Find fantastic fares on domestic and international flights that suit your travel requirements and budget needs by heading to Orbitz. Orbitz has your cheap air tickets for flights from Chicago to Florida Keys.
Flights from Chicago to Florida Keys at bargain prices
Budgeting and hidden costs should be the least of your concerns when planning a trip. Your priority should be planning all the things you want to do during your stay. With our low fares on Chicago to Florida Keys flights, you know you are getting the best deal for your vacation or business trip budget—and not incurring hidden costs or paying for over-priced tickets offered by some airlines. We want to help you enjoy your trip the way you deserve.
Remain up-to-date on your flights from Chicago to Florida Keys
Orbitz ensures that you remain up-to-date with the latest flight information by sending free alerts to your mobile device or email. Additionally, our cutting-edge mobile apps let iPhone and Android users the capability to receive status reports and review baggage and gate claim details on their mobile devices. You can even book hotels or car rentals to go along with your Chicago to Florida Keys flights or view your itinerary using these useful and easy-to-use apps.
Orbitz booking discounts for Chicago to Florida Keys flights
Orbitz can remember your information, including numbers your frequent flyer and airline loyalty memberships, so you don’t have to re-enter information when you book your flights from Chicago to Florida Keys or other flights. Not only does this make booking flights a breeze, you no longer have to go through the hassle of looking up your frequent flyer numbers to add them to your flight reservation.
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.