Selected fares from Chicago to Florida Keys
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Chicago to Florida Keys Intro 9
Looking for guaranteed low prices on Chicago to Florida Keys flights? Orbitz is your source and much more. From cutting-edge mobile tools to great deals, Orbitz makes it easy to book your dream vacation.
Frequent Flyers Earn Miles
Earn frequent flyer miles or points on Orbitz flights from Chicago to Florida Keys. When booking your Chicago to Florida Keys flights, have your frequent flyer number on hand and add it where prompted. Your Orbitz account can store your number for future use, meaning you never miss out on your rewards.
Book Orbitz on the Go
With the Orbitz mobile apps for Android and iPhone, you no longer have to be sitting at your desk to book Chicago to Florida Keys flights. With a few easy clicks, you can book your flights, research hotel rooms, and check your flight status and other important flight information.
Easily Plan Your Vacation
Not only does Orbitz offer great prices on flights from Chicago to Florida Keys, but you will also find fantastic deals on hotels, cruises, and vacation activities. Never miss out on that dream trip or waste hours waiting in long lines—you can buy tickets to attraction in advance with Orbitz to guarantee admission to your favorite places.
Best Deals At Your Fingertips
Orbitz combines low prices on Chicago to Florida Keys flights with discounts on quality hotels. Using Orbitz’s Display Matrix, you can see all your options and savings easily. With our low price guarantee, you know you have the best deals at your fingertips.
Save more with Florida Keys Flight + Hotel packages
Westgate South Beach Oceanfront Resort
4.0 out of 5.0Sat, Sep 30 - Wed, Oct 4
CHI-All Airports - Miami Intl.
$432
per person
Daddy O Hotel
4.0 out of 5.0Sat, Sep 30 - Wed, Oct 4
CHI-All Airports - Miami Intl.
$260
per person
The Palms Hotel & Spa
4.0 out of 5.0Sat, Sep 30 - Wed, Oct 4
CHI-All Airports - Miami Intl.
$522
per person
Crest Hotel Suites
3.0 out of 5.0Fri, Oct 6 - Thu, Oct 12
O'Hare Intl. - Miami Intl.
$600
per person
Faena Hotel Miami Beach
5.0 out of 5.0Sat, Sep 30 - Wed, Oct 4
CHI-All Airports - Miami Intl.
$900
per person
W Fort Lauderdale
4.0 out of 5.0Mon, Sep 25 - Sat, Sep 30
CHI-All Airports - Miami Intl.
$600
per person
SLS Hotel South Beach
4.0 out of 5.0Sat, Oct 7 - Wed, Oct 11
CHI-All Airports - Miami Intl.
$798
per person
Four Seasons Hotel Miami
5.0 out of 5.0Sat, Sep 30 - Wed, Oct 4
CHI-All Airports - Miami Intl.
$584
per person
Turnberry Isle Miami, Autograph Collection
4.5 out of 5.0Sat, Sep 30 - Wed, Oct 4
CHI-All Airports - Miami Intl.
$506
per person
Newport Beachside Resort
3.0 out of 5.0Sat, Sep 30 - Wed, Oct 4
CHI-All Airports - Miami Intl.
$376
per person
Fashion Boutique Hotel
3.5 out of 5.0Tue, Oct 3 - Sat, Oct 7
CHI-All Airports - Miami Intl.
$289
per person
The St. Regis Bal Harbour Resort
5.0 out of 5.0Sat, Sep 30 - Wed, Oct 4
CHI-All Airports - Miami Intl.
$1,089
per person
More to explore for Chicago to Florida Keys
Explore Florida Keys with Orbitz's Travel Guides to find the best flights, cars, vacation packages and more!
Flights from Cities near Chicago
Flights to Cities near Florida Keys
Other Flights to Florida Keys
- New York to Florida Keys
- Caracas to Florida Keys
- Chicago to Florida Keys
- Atlanta to Florida Keys
- Tianjin to Florida Keys
- Shenzhen to Florida Keys
- Hong Kong to Florida Keys
- Bogota to Florida Keys
- Shanghai to Florida Keys
- Guangzhou to Florida Keys
- Philadelphia to Florida Keys
- Buenos Aires to Florida Keys
- Chongqing to Florida Keys
Other Flights from Chicago
- Chicago to Las Vegas
- Chicago to Los Angeles
- Chicago to Orlando
- Chicago to New York
- Chicago to Cancun
- Chicago to Phoenix
- Chicago to Fort Lauderdale
- Chicago to London
- Chicago to Denver
- Chicago to Mexico City
- Chicago to Tampa
- Chicago to New Orleans
- Chicago to San Francisco
- Chicago to Miami
- Chicago to Atlanta
- Chicago to Fort Myers
- Chicago to Guadalajara
- Chicago to Toronto
- Chicago to Montreal
Related Flights from Florida Keys to Chicago
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.
