$104 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, Jan 24 - Sat, Jan 31
ORD
O'Hare Intl.
EYW
Key West Intl.
$411 Roundtrip, found 3 days ago
$411
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jan 24 from O'Hare Intl. to Key West Intl., returning Sat, Jan 31, priced at $411 found 3 days ago
Fri, Jan 23 - Tue, Jan 27
MDW
Midway Intl.
EYW
Key West Intl.
$477 Roundtrip, found 5 days ago
$477
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jan 23 from Midway Intl. to Key West Intl., returning Tue, Jan 27, priced at $477 found 5 days ago

Airfares from $104 One Way, $207 Round Trip from Chicago to Key West

Prices starting at $207 for return flights and $104 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 - Fri, Feb 27
ORD
Chicago
EYW
Key West
$207 Roundtrip, found 6 hours ago
$207
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Mon, Feb 23 from Chicago to Key West, returning Fri, Feb 27, priced at $207 found 6 hours ago
Mon, Feb 16 - Thu, Feb 19
ORD
Chicago
EYW
Key West
$209 Roundtrip, found 2 hours ago
$209
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Mon, Feb 16 from Chicago to Key West, returning Thu, Feb 19, priced at $209 found 2 hours ago
Thu, Feb 19 - Thu, Feb 26
ORD
Chicago
EYW
Key West
$210 Roundtrip, found 2 hours ago
$210
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Feb 19 from Chicago to Key West, returning Thu, Feb 26, priced at $210 found 2 hours ago
Mon, Mar 2 - Fri, Mar 6
ORD
Chicago
EYW
Key West
$216 Roundtrip, found 17 hours ago
$216
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Mon, Mar 2 from Chicago to Key West, returning Fri, Mar 6, priced at $216 found 17 hours ago
Sun, Feb 8 - Thu, Feb 12
ORD
Chicago
EYW
Key West
$229 Roundtrip, found 2 hours ago
$229
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sun, Feb 8 from Chicago to Key West, returning Thu, Feb 12, priced at $229 found 2 hours ago

Key West economy flight packages

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
4.0-star property

Oceans Edge Key West Resort, Hotel & Marina

9/10 Wonderful! (1,736 reviews)

Feb 21 - Feb 27

6 night stay

Chicago (CHI) to Key West (EYW)

United • Roundtrip • Coach
Save 100% on your flight
Price was $2,176, price is now $1,262 per person
$1,262
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

Lighthouse Hotel - Key West Historic Inns
3.5-star property

Lighthouse Hotel - Key West Historic Inns

9/10 Wonderful! (831 reviews)

Feb 21 - Feb 27

6 night stay

Chicago (CHI) to Key West (EYW)

United • Roundtrip • Coach
Save 100% on your flight
Price was $2,965, price is now $1,923 per person
$1,923
per person
found 1 day ago
The rooms ideally could have been a bit cleaner. For instance vacuum underneath the furnishings. Great breakfast and the loft room Was fantastic. Close to everything yet not in the congestion.

Reviewed on Jan 15, 2026

Pier House Resort & Spa
4.0-star property

Pier House Resort & Spa

9/10 Wonderful! (1,006 reviews)

Feb 21 - Feb 27

6 night stay

Chicago (CHI) to Key West (EYW)

United • Roundtrip • Coach
Save 100% on your flight
Price was $3,437, price is now $2,255 per person
$2,255
per person
found 1 day ago
This is a wonderful resort in Key West that has great amenities and located on Duval Street! Highly recommend.

Reviewed on Jun 24, 2025

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Key West packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort
2.5-star property

Ibis Bay Beach Resort

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

Mar 11 - Mar 18

7 night stay

Chicago (MDW) to Key West (EYW)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,287, price is now $1,630 per person
$1,630
per person
just found
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

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 11 - Mar 18

7 night stay

Chicago (MDW) to Key West (EYW)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,120, price is now $1,930 per person
$1,930
per person
just found
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 11 - Mar 18

7 night stay

Chicago (MDW) to Key West (EYW)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $5,297, price is now $3,442 per person
$3,442
per person
just found
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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Key West first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West
4.0-star property

The Perry Hotel & Marina Key West

9.4/10 Exceptional! (1,151 reviews)

Mar 7 - Mar 14

7 night stay

Chicago (ORD) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $3,054, price is now $2,420 per person
$2,420
per person
found 3 hours ago
Check-in was as smooth as could be. Reps made sure we had access to a luggage cart right away. Property very clean. Room staff could not have been nicer. Would certainly book again

Reviewed on Aug 12, 2025

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (505 reviews)

Mar 7 - Mar 14

7 night stay

Chicago (ORD) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $5,105, price is now $3,603 per person
$3,603
per person
found 3 hours 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

Winslow's Bungalows - Key West Historic Inns
4.0-star property

Winslow's Bungalows - Key West Historic Inns

9.2/10 Wonderful! (1,044 reviews)

Mar 7 - Mar 14

7 night stay

Chicago (ORD) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $3,462, price is now $2,518 per person
$2,518
per person
found 3 hours ago
Great place! Great staff!

Reviewed on Dec 26, 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

The best fares for Chicago to Key West flights are always found on Orbitz. With superior discounts and the latest innovations in mobile access, your ideal trip starts with Orbitz.

The Easy Way to Plan Travel Cheaply

We provide access to many low-cost vacation packages and travelers can mix and match airlines when scheduling their flights for the best prices and flight times. Finding cheap tickets on flights from Chicago to Key West is easy when you make Orbitz your #1 travel planner.

Book Chicago to Key West Flights With Mobile Apps

Our iPhone and Android mobile apps can be used to compare and book flights from Chicago to Key West. These apps are perfect for checking the status of flights, gate and baggage claims details, car rental rates, and for receiving alerts on special savings that are exclusive to mobile users. Mobile app users can even score great rates when booking hotel rooms. You can compare hotels, virtually view photo galleries, and check out user reviews using the app, as well as find out which ones are closest to you.

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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.