$143 Cheap flight deals from Chicago (CHI) to Key West (EYW)

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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.

Sat, Aug 2 - Tue, Aug 5
MDW
Midway Intl.
EYW
Key West Intl.
$379 Roundtrip, found 6 days ago
$379
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Aug 2 from Midway Intl. to Key West Intl., returning Tue, Aug 5, priced at $379 found 6 days ago
Sat, Aug 2 - Tue, Aug 5
ORD
O'Hare Intl.
EYW
Key West Intl.
$396 Roundtrip, found 3 days ago
$396
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Key West Intl., returning Tue, Aug 5, priced at $396 found 3 days ago

Airfares from $143 One Way, $249 Round Trip from Chicago to Key West

Prices starting at $249 for return flights and $143 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.

Tue, Apr 28 - Tue, May 5
ORD
Chicago
EYW
Key West
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select United flight, departing Tue, Apr 28 from Chicago to Key West, returning Tue, May 5, priced at $249 found 1 day ago
Sat, Jan 3 - Sat, Jan 10
ORD
Chicago
EYW
Key West
$260 Roundtrip, found 21 hours ago
$260
Roundtrip
found 21 hours ago
Select United flight, departing Sat, Jan 3 from Chicago to Key West, returning Sat, Jan 10, priced at $260 found 21 hours ago
Tue, Apr 28 - Tue, May 5
ORD
Chicago
EYW
Key West
$265 Roundtrip, found 1 day ago
$265
Roundtrip
found 1 day ago
Select United flight, departing Tue, Apr 28 from Chicago to Key West, returning Tue, May 5, priced at $265 found 1 day ago
Tue, Oct 14 - Wed, Oct 22
MDW
Chicago
EYW
Key West
$269 Roundtrip, found 13 hours ago
$269
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Oct 14 from Chicago to Key West, returning Wed, Oct 22, priced at $269 found 13 hours ago
Tue, Jan 27 - Sat, Jan 31
ORD
Chicago
EYW
Key West
$270 Roundtrip, found 14 hours ago
$270
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Jan 27 from Chicago to Key West, returning Sat, Jan 31, priced at $270 found 14 hours ago

Key West economy flight packages

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

Hyatt Vacation Club at Windward Pointe, Key West

9.6/10 Exceptional! (1,002 reviews)

Sep 5 - Sep 8

3 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

Almond Tree Inn Hotel - Adults Only
3.5-star property

Almond Tree Inn Hotel - Adults Only

10/10 Exceptional! (1,002 reviews)

Sep 11 - Sep 15

4 night stay

Chicago (CHI) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
As always, Almond Tree Inn was a bright spot in our latest trip to Key West. I’ve stayed here several times over the years and everything about Almond Tree is top notch, from the superbly attentive and friendly staff to the well-appointed and maintained property. You always feel special staying here and this trip was no exception. As Florida locals, we look forward to our stays with you each and every time- THANK YOU!

Reviewed on May 26, 2025

Orchid Key Inn - Adults Only
3.5-star property

Orchid Key Inn - Adults Only

9.8/10 Exceptional! (1,005 reviews)

Sep 11 - Sep 15

4 night stay

Chicago (CHI) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
Great place. Very cool retro motel that’s been renovated. Room was a little small but very comfortable and clean. There’s a nice bar with great cocktails. Staff are friendly and attentive. The location was great. Central to everything and very walkable to most of the popular sites.

Reviewed on Jan 20, 2025

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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

If you are looking to find the best deals on Chicago to Key West flights, look no further than Orbitz. Orbitz offers guaranteed low prices as well as cutting-edge mobile tools to help you book cheap flights from Chicago to Key West.

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Orbitz keeps you updated on information that’s relevant to your flights from Chicago to Key West. We can send you and six of your personal contacts free travel alerts via SMS text, voicemail, or email, so you instantly know about flight delays or changes.

Keep More Money in Your Pocket With Discount Flights

Orbitz looks for the best deals on Chicago to Key West flights for you. Mix and match airlines for your departing and return flights to fit your travel schedule and budget.

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.