$55 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, Feb 7 - Sat, Feb 14
ORD
O'Hare Intl.
EYW
Key West Intl.
$421 Roundtrip, found 1 day ago
$421
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Feb 7 from O'Hare Intl. to Key West Intl., returning Sat, Feb 14, priced at $421 found 1 day ago
Fri, Feb 6 - Tue, Feb 10
MDW
Midway Intl.
EYW
Key West Intl.
$477 Roundtrip, found 2 days ago
$477
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Feb 6 from Midway Intl. to Key West Intl., returning Tue, Feb 10, priced at $477 found 2 days ago
Sun, Feb 8 - Sun, Feb 15
RFD
Greater Rockford
EYW
Key West Intl.
$879 Roundtrip, found 6 days ago
$879
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Feb 8 from Greater Rockford to Key West Intl., returning Sun, Feb 15, priced at $879 found 6 days ago

Airfares from $55 One Way, $99 Round Trip from Chicago to Key West

Prices starting at $99 for return flights and $55 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.

Mon, Feb 23 - Thu, Feb 26
ORD
Chicago
EYW
Key West
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Feb 23 from Chicago to Key West, returning Thu, Feb 26, priced at $99 found 1 day ago
Mon, Feb 23 - Thu, Feb 26
ORD
Chicago
EYW
Key West
$106 Roundtrip, found 2 days ago
$106
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Mon, Feb 23 from Chicago to Key West, returning Thu, Feb 26, priced at $106 found 2 days ago
Mon, Mar 2 - Thu, Mar 5
ORD
Chicago
EYW
Key West
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Mon, Mar 2 from Chicago to Key West, returning Thu, Mar 5, priced at $110 found 2 days ago
Thu, Feb 26 - Thu, Mar 5
ORD
Chicago
EYW
Key West
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Feb 26 from Chicago to Key West, returning Thu, Mar 5, priced at $144 found 2 days ago
Sat, Sep 12 - Wed, Sep 16
ORD
Chicago
EYW
Key West
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select United flight, departing Sat, Sep 12 from Chicago to Key West, returning Wed, Sep 16, priced at $249 found 1 day ago

Key West economy flight packages

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

Hyatt Vacation Club at Sunset Harbor, Key West

8.4/10 Very Good! (315 reviews)

Apr 2 - Apr 5

3 night stay

Chicago (ORD) to Key West (EYW)

Spirit Airlines • Non-stop • Coach

Key West (EYW) to Chicago (ORD)

American Airlines • Non-stop • Coach
Price was $1,505, price is now $1,125 per person
$1,125
per person
found 1 day ago
Great place to stay. Location is excellent, its walking distance to so many attractions. Had a great stay.

Reviewed on Dec 1, 2024

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (505 reviews)

Mar 28 - Apr 3

6 night stay

Chicago (CHI) to Key West (EYW)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $4,034, price is now $2,907 per person
$2,907
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.

Reviewed on Jan 5, 2025

Ibis Bay Beach Resort
2.5-star property

Ibis Bay Beach Resort

8.2/10 Very Good! (2,000 reviews)

Mar 28 - Apr 3

6 night stay

Chicago (CHI) to Key West (EYW)

American Airlines • Roundtrip • Coach
Price was $2,343, price is now $1,776 per person
$1,776
per person
found 1 day ago
Room was very small. Window shade wouldn't block the light beaming in my window all night. Not that big of a deal though, i wasn't there for the room. The beach was pretty much rock, so that wasn't great. The facilities offer plenty for you. Bar, restaurant, boat rentals. Tours. My favorite was probably be the hammocks a plenty

Reviewed on Jul 15, 2025

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Key West first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Reach Key West, Curio Collection by Hilton
4.0-star property

The Reach Key West, Curio Collection by Hilton

8.4/10 Very Good! (1,001 reviews)

Mar 25 - Mar 29

4 night stay

Chicago (ORD) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,578, price is now $2,030 per person
$2,030
per person
found 1 day ago
Beautiful beach, great restaurant

Reviewed on Jan 22, 2026

Oceans Edge Key West Resort, Hotel & Marina
4.0-star property

Oceans Edge Key West Resort, Hotel & Marina

9/10 Wonderful! (1,736 reviews)

Mar 25 - Mar 29

4 night stay

Chicago (ORD) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,888, price is now $2,092 per person
$2,092
per person
found 1 day ago
We LOVED the setting and the surrounding area! Absolutely beautiful! Be aware the hotel IS in the airport landing zone. If you like to watch/hear commercial planes you'll be very happy. Ask for a room on the top floor only - so you can (1) look over the marina AND (2) so you won't hear people moving chairs on their balcony above you. The max/min air conditioning is centrally controlled. If you want it colder than 67, you will not be able to. Not sure what the max heat was. Be extra vigilant about putting a thick towel on the floor to soak up any water that gets past the shower door. It WILL happen! Please do not slip on the wet tile floor! Be aware that if you want/need a later checkout, they will charge you an additional $50/hour past their usual checkout time of 11am. Be prepared for onsite meal expenses. They are very good, but they ARE on the pricy side. Our particular room smelled strongly of smoke on arrival. I'm nearly POSITIVE we asked for a nonsmoking room as we both have underlying medical problems that preclude exposre to smoke. Perhaps call ahead to ENSURE you get a nonsmoking on arrival. The entire hotel was booked so we did not have any other choice.

Reviewed on Dec 28, 2025

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (505 reviews)

Mar 25 - Mar 29

4 night stay

Chicago (ORD) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $3,556, price is now $2,722 per person
$2,722
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.

Reviewed on Jan 5, 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

Getting a spectacularly low fare on Chicago to Key West 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 Key West, discount hotel accommodations, cheap car rentals, and more.

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Stay in Your Budget and Still Get Great Accommodations

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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!

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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.