$137 Cheap flight deals from Chicago (CHI) to Key West (EYW)

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

This Weekend's Flight Deals from Chicago to Key West

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.

Fri, Aug 22 - Mon, Aug 25
ORD
O'Hare Intl.
EYW
Key West Intl.
$370 Roundtrip, found 2 days ago
$370
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Aug 22 from O'Hare Intl. to Key West Intl., returning Mon, Aug 25, priced at $370 found 2 days ago

Airfares from $137 One Way, $269 Round Trip from Chicago to Key West

Prices starting at $269 for return flights and $137 for one-way flights to Key West were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Sep 17 - Wed, Sep 24
MDW
Chicago
EYW
Key West
$269 Roundtrip, found 4 days ago
$269
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep 17 from Chicago to Key West, returning Wed, Sep 24, priced at $269 found 4 days ago
Tue, Nov 18 - Mon, Nov 24
ORD
Chicago
EYW
Key West
$269 Roundtrip, found 5 days ago
$269
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 18 from Chicago to Key West, returning Mon, Nov 24, priced at $269 found 5 days ago
Tue, Dec 9 - Tue, Dec 16
ORD
Chicago
EYW
Key West
$272 Roundtrip, found 4 days ago
$272
Roundtrip
found 4 days ago
Select United flight, departing Tue, Dec 9 from Chicago to Key West, returning Tue, Dec 16, priced at $272 found 4 days ago
Sat, Jan 31 - Sat, Feb 7
ORD
Chicago
EYW
Key West
$273 Roundtrip, found 9 hours ago
$273
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Sat, Jan 31 from Chicago to Key West, returning Sat, Feb 7, priced at $273 found 9 hours ago
Tue, Sep 16 - Wed, Sep 24
MDW
Chicago
EYW
Key West
$274 Roundtrip, found 4 days ago
$274
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 16 from Chicago to Key West, returning Wed, Sep 24, priced at $274 found 4 days ago

Key West economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West
3.5-star property

Hyatt Vacation Club at Beach House, Key West

9.2/10 Wonderful! (1,004 reviews)

Sep 15 - Sep 19

4 night stay

Chicago (CHI) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
The hotel was very nice. The bathroom in the primary sweet was amazing. Suzy at the tiki hut on the property was great!

Reviewed on May 16, 2025

Hyatt Vacation Club at Windward Pointe, Key West
3.5-star property

Hyatt Vacation Club at Windward Pointe, Key West

9.6/10 Exceptional! (1,015 reviews)

Sep 15 - Sep 19

4 night stay

Chicago (CHI) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
Such a nice property

Reviewed on Jun 3, 2025

Orchid Key Inn - Adults Only
3.5-star property

Orchid Key Inn - Adults Only

9.8/10 Exceptional! (1,006 reviews)

Sep 15 - Sep 19

4 night stay

Chicago (CHI) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
This is a great place to relax, great breakfast, pool, bar, steps away from everything on Duval. I would give it a perfect score other than Alex the bartender being a little….let’s call it snitty. We would stay here again.

Reviewed on Aug 1, 2025

Don't see what you're looking for?
See all available trips from Chicago to Key West
View all trips

More About Flying To Key West from Chicago

Route Information for Flights from Chicago to Key West

Origin Airport IATA Code
CHI
Destination Airport IATA Code
EYW
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Key West

Orbitz has your discount air ticket deals for flights from Chicago to Key West. The guaranteed low prices from flights and hotels to car rentals and vacation packages make Orbitz the perfect travel website for budget trip planning.

Use Orbitz to Earn Frequent Flyer Miles

You know you can find great fares with Orbitz—but did you know you don’t have to give up earning miles or points towards your frequent flyer program? If you’re a member of a frequent flyer program, you can use Orbitz to find bargain prices for flights from Chicago to Key West and still earn points or miles. All you have to do is add your frequent flyer account number as you book your tickets online. After you complete your travel plans, you can choose to keep your account number in your personal account profile so that you can automatically add it to your next Orbitz reservation.

Orbitz Keeps You Up-to-Date With Instant Flight Alerts

While Orbitz gives you access to cheap tickets for Chicago to Key West flights, the travel site also offers free email, voice, or text message alerts to keep you informed of any abrupt changes or delays that affect your travel. You can even choose to have the alerts sent to up to six of your mobile or email contacts to keep your friends in the loop.

Bargain Chicago to Key West Flights With Mobile Apps

Download the cutting-edge Orbitz app for either Android or iPhone, and use it to check on the status of your upcoming flights from Chicago to Key West at any time. These apps also make it easy for you to book discount hotel rates in your destination city and check for deals on future Chicago to Key West flights.

Frequently asked questions

Am I able to catch a flight from Chicago to Key West now?
The Covid-19 Travel Advisor can answer all your queries about travel restrictions and quarantine when flying from Chicago to Key West.
Are there non-stop flights from Chicago to Key West?
Two carriers operate nonstop flights from Chicago, IL Airport (ORD-O'Hare Intl.) to Key West, FL Airport (EYW-Key West Intl.) — United Airlines and American Airlines. They'll take you where you need to go in style and comfort.
What is the shortest flight from Chicago to Key West?
The shortest flight from Midway Intl. Airport (MDW) to EYW is around 3 hours and 32 minutes. Order a wine from the drink trolley, hone your travel itinerary or get to know your seat mate — you'll have plenty of time on this medium-haul trip.
What airlines fly from Chicago to Key West most frequently?
There are a few airlines offering frequent flights from O'Hare Airport to Key West, FL Airport (EYW-Key West Intl.), including United Airlines (UA). A top pick for many travelers, it operates 60 flights on this route each month. Alternatively, book your favorite aisle (or window) seat with American Airlines (AA). You'll have 52 monthly flights between Chicago and Key West to choose from with this carrier.
If I am not able to travel due to COVID-19, can I cancel my flight to Key West?
We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Key West have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Key West with flexible change policies?
In most cases you'll have the option to reschedule your flight to Key West without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.
How can I save money on flights?
To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

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.