Beginning of main content

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Fares from $28 One Way, $65 Round Trip from Chicago to Florida Keys

Prices starting at $65 for return flights and $28 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.

Need A Hotel In Florida Keys?

More About Flying To Florida Keys from Chicago

Flights from Chicago to Florida Keys - Frequently Asked Questions

Are there non-stop flights from Chicago to Florida Keys?

Yes, you can fly from Chicago, IL Airport (ORD-O'Hare Intl.) to Key West, FL Airport (EYW-Key West Intl.) with American Airlines, the only carrier offering direct flights on this route.

What is the shortest flight from Chicago to Florida Keys?

From Chicago, the thrilling sights and sounds of Florida Keys are at least 3 hours and 5 minutes away. Lock in your favorite seat, or maybe even one with more legroom, and get to your destination in pure comfort.

What airlines fly from Chicago to Florida Keys most frequently?

American Airlines is the most frequent airline servicing the Chicago to Florida Keys route. Take your pick of 14 flights per month with this carrier.

Route Information for Flights from Chicago to Florida Keys

Origin Airport IATA CodeCHI
Destination Airport IATA CodeMIA
Distance1199 mi
Direct Flight AirlinesAmerican Airlines, Alaska Airlines, Frontier Airlines, SAS, Volaris, Air New Zealand, United Airlines
Earliest Flight Arrival12:59PM UTC
Latest Flight Arrival3:36AM UTC

Flights Review

Feb 17, 2020

Service was good..1. Quick boarding, 2. No bothered by attending 3. Quick flight.

Feb 12, 2020

Traveled with a special needs child and everything offered my American Airlines was very helpful and accommodating.

Jan 31, 2020

took forever to get bags. Everything else was greatw

Jan 19, 2020

Broke my suitcase in baggage handling

Jan 7, 2020

I will definitely upgrade my seating on my next flight.

Jan 5, 2020

Got charged for checking a bag I thought was free but besides that it was good

Jan 3, 2020

Great flight attendants

Dec 26, 2019

Good service

Nov 23, 2019

Everyone was great.

Oct 18, 2019

American is by far my favorite airline. I will only fly American or occasionally southwest Bc I have 5 kids and SW tends to be more affordable.

Chicago to Florida Keys

Getting a spectacularly low fare on Chicago to Florida Keys flights is always possible when you use Orbitz as your personal travel planner. Orbitz is your essential travel resource for low cost flights from Chicago to Florida Keys, discount hotel accommodations, cheap car rentals, and more.

Research and Book Chicago to Florida Keys Flights on the Go

Our free cutting-edge mobile apps for iPad, Android, and iPhone make it easy to find the best fares when researching and booking flights from Chicago to Florida Keys. You can also use the apps to check your flight status, find baggage claims details, and get exclusive mobile discount rates on car rentals and hotels.

Earn Miles and Points for Your Frequent Flyer Program

Build up points or miles for your frequent flyer plan with qualifying Chicago to Florida Keys flights. Simply add your frequent flyer number when booking your domestic or international flights or enter the numbers in your Orbitz account profile to automatically add them to your bookings.

Flight Alerts Take the Hassle out of Travel

You can get email, SMS text, or voicemail updates regarding any major changes to your flights from Chicago to Florida Keys. These free alerts can also be sent to as many as six additional contacts, ensuring that your friends, colleagues, or family are aware of changes to your arrival time.

Stay in Your Budget and Still Get Great Accommodations

Orbitz shoppers can access affordable vacation packages and have the option of booking their departure and arrival flights through different airlines, making travel less costly and more convenient. The best prices on flights from Chicago to Florida Keysare always found on Orbitz.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 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.