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Save on Packages
Up to $536 by booking Flight + Hotel together*
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 42
Planning a trip is rarely straight forward, especially when searching for cheap deals. At Orbitz.com, we make it easier than anywhere else by providing you with guaranteed low prices. So if you are looking for Chicago to Florida Keys flights at low cost, you will not be disappointed.
Cruising for a bargain deal
Regardless of your destination, we always provide you fantastic bargains for your trip, and that includes on hotels and even cruises. We offer budget air fares on flights from Chicago to Florida Keys so you can reach your destination with more money in your pocket to spend.
Cheap Chicago to Florida Keys flights that lead to rewards
Get rewarded for your cheap Chicago to Florida Keys flights by earning miles and points for your airline loyalty or frequent flyer program. Rack up the miles by flying cheaply with Orbitz so you can earn free flights and other savings with your favorite airlines. Just enter your frequent flyer number when booking your discount fare on flights from Chicago to Florida Keys on Orbtiz.com.
Quality combinations
If you require budget Chicago to Florida Keys flights and a bargain hotel to go with it, Orbitz will wow you with the great combinations we can offer. The quality is always high and always a superb value.
Even last minute bookings on our apps
You do not need to be tied to your desktop computer to make your booking. With our cutting-edge mobile tools, you can search for those low cost deals anywhere, anytime. Our app gives you the freedom to secure flights from Chicago to Florida Keys at the very last minute from your mobile device.
Save more with Florida Keys Flight + Hotel packages
Pier House Resort & Spa
4.0 out of 5.0Mon, May 28 - Mon, Jun 4
CHI - EYW
$1,687
per person
La Concha Hotel & Spa
4.0 out of 5.0Mon, May 28 - Mon, Jun 4
CHI - EYW
$1,353
per person
Fairfield Inn and Suites by Marriott Key West
2.5 out of 5.0Mon, May 28 - Mon, Jun 4
CHI - EYW
$1,183
per person
Best Western Key Ambassador Resort Inn
2.5 out of 5.0Mon, May 28 - Mon, Jun 4
CHI - EYW
$1,145
per person
Playa Largo Resort & Spa, Autograph Collection
3.5 out of 5.0Sat, Jun 9 - Sat, Jun 16
CHI - EYW
$1,521
per person
The Moorings Village
3.5 out of 5.0Sat, Jun 9 - Sat, Jun 16
CHI - EYW
$3,905
per person
Tranquility Bay Beachfront Hotel and Resort
4.0 out of 5.0Sat, Jun 9 - Sat, Jun 16
CHI - EYW
$1,761
per person
The Saint Hotel Key West, Autograph Collection
3.5 out of 5.0Sat, Jun 9 - Sat, Jun 16
CHI - EYW
$1,724
per person
MB at Key Largo (Formerly Dove Creek Lodge)
3.0 out of 5.0Sat, Jun 9 - Sat, Jun 16
CHI - EYW
$1,283
per person
Indigo Reef Resort Villas & Marina by KeysCaribbean
3.5 out of 5.0Sat, Jun 9 - Sat, Jun 16
CHI - EYW
$2,121
per person
Ocean Pointe Suites at Key Largo
3.0 out of 5.0Sat, Jun 9 - Sat, Jun 16
CHI - EYW
$1,419
per person
Holiday Inn Key Largo
3.0 out of 5.0Sat, Jun 9 - Sat, Jun 16
CHI - EYW
$1,150
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!
Airports near Florida Keys
Flights from Cities near Chicago
Flights to Cities near Florida Keys
Other Flights to Florida Keys
- Chicago to Florida Keys
- Santo Domingo to Florida Keys
- Mexico City to Florida Keys
- New York to Florida Keys
- Denver to Florida Keys
- Buenos Aires to Florida Keys
- Medellin to Florida Keys
- Lima to Florida Keys
- Caracas to Florida Keys
- Guayaquil to Florida Keys
- Philadelphia to Florida Keys
- San Jose to Florida Keys
- Quito to Florida Keys
- Bogota to Florida Keys
- Santiago to Florida Keys
- San Juan to Florida Keys
* Savings based on all holiday package bookings with Flight + Hotel on Orbitz.com from July 1, 2015 to June 30, 2016, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.
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.
