ORD - EYW

$95 Find Cheap Flights from Chicago O'Hare Airport to Key West

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Key West departing on 2/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Key West

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$289
Overall average: $549
American Airlines
Fri 3/13Mon 3/16
ORD - EYW • 1 stop
Cheapest non-stop
$297
Typical prices: $421-$815
American Airlines
Fri 3/6Fri 3/13
ORD - EYW • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers extra legroom benefits.
Expect long lines at ORD security during peak times.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
United Airlines
Cheapest • from $289 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
June
Cheapest • 17% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Key West!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from O'Hare Intl to Key West (ORD-EYW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Key West that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Key West

Fri, Mar 13 - Mon, Mar 16
American Airlines Logo
1:39 pm - 10:37 pm
ORD
-
EYW
7h 58m1 stop
American Airlines Logo
6:49 pm - 9:36 pm
EYW
-
ORD
3h 47mnonstop
$289American Airlines
Fri, Apr 3 - Wed, Apr 8
Multiple Airlines Logo
4:00 pm - 2:38 pm
ORD
-
EYW
21h 38m1 stop
Multiple Airlines Logo
11:51 am - 4:47 pm
EYW
-
ORD
5h 56m1 stop
$290Multiple Airlines
Thu, Jan 29 - Sun, Feb 1
Spirit Airlines Logo
5:15 am - 11:56 am
ORD
-
EYW
5h 41m1 stop
Spirit Airlines Logo
12:51 pm - 11:47 pm
EYW
-
ORD
11h 56m1 stop
$291Spirit Airlines
Sat, Jan 17 - Sat, Jan 24
Multiple Airlines Logo
12:44 pm - 9:26 am
ORD
-
EYW
19h 42m1 stop
Multiple Airlines Logo
10:49 am - 4:35 pm
EYW
-
ORD
6h 46m1 stop
$292Multiple Airlines
Wed, Mar 18 - Sun, Mar 22
Multiple Airlines Logo
4:18 pm - 9:06 am
ORD
-
EYW
15h 48m1 stop
Multiple Airlines Logo
12:25 pm - 11:26 am
EYW
-
ORD
24h 01m1 stop
$293Multiple Airlines
Fri, Jan 30 - Tue, Feb 3
Delta Logo
5:30 am - 11:25 am
ORD
-
EYW
4h 55m1 stop
Delta Logo
6:06 pm - 11:56 pm
EYW
-
ORD
6h 50m1 stop
$294Delta
Mon, Feb 2 - Thu, Feb 5
Spirit Airlines Logo
7:20 am - 1:30 pm
ORD
-
EYW
5h 10m1 stop
Spirit Airlines Logo
12:51 pm - 9:12 am
EYW
-
ORD
21h 21m3 stops
$295Spirit Airlines
Wed, Mar 18 - Thu, Mar 26
Multiple Airlines Logo
4:51 pm - 9:06 am
ORD
-
EYW
15h 15m2 stops
Multiple Airlines Logo
11:01 am - 4:51 pm
EYW
-
ORD
6h 50m1 stop
$296Multiple Airlines
Sun, Feb 15 - Wed, Feb 18
American Airlines Logo
1:53 pm - 6:19 pm
ORD
-
EYW
3h 26mnonstop
American Airlines Logo
6:53 pm - 9:40 pm
EYW
-
ORD
3h 47mnonstop
$297American Airlines
Fri, Jan 30 - Sun, Feb 1
Multiple Airlines Logo
8:43 pm - 10:09 am
ORD
-
EYW
12h 26m2 stops
Multiple Airlines Logo
12:51 pm - 10:49 pm
EYW
-
ORD
10h 58m1 stop
$298Multiple Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Key West flights

Get data-powered insights and trends into flights from O'Hare Intl to Key West to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Key West?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Key West clicked on KAYAK for each day over the last 12 months.

When flying from Chicago O'Hare Airport to Key West, you should consider leaving on a Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago O'Hare Airport, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Key West?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Key West, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Key West is June, where tickets cost $362 (return) on average. On the other hand, the most expensive months are March and February, where the average cost of round-trip tickets is $549 and $504 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Key West?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $412 on average.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Key West?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Key West, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Key West, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Expert advice

Expert advice for your flight from O'Hare Intl to Key West

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Consider Basic Economy for budget travel; restrictions include late boarding and no seat assignment.


Main Cabin Extra offers early boarding and complimentary drinks, ideal for longer flights.

United Airlines

Economy Plus provides up to 6 inches more legroom than standard economy seats.


Purchase Priority Boarding to avoid gate-checking your carry-on due to overhead bin space.

Airports
ORD

Security lines at ORD can be long during peak times. Arrive early to ensure a smooth departure experience.

EYW

At EYW, taxis and rideshares are readily available, making it easy to reach Key West's attractions quickly.

Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Paul Rubio

Paul Rubio

Expert on EYW

Paul Rubio

Paul Rubio

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

Read more

Good to know

Low seasonAugust
Cheapest flight$95
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Chicago O'Hare Airport to Key West

When to book flights from O'Hare Intl to Key West

Are your dates flexible? Find out the best times to travel from O'Hare Intl to Key West based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago O'Hare Airport to Key West flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Key West?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Key West was $95 for a one-way ticket and $289 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and Key West?

    A passport is not required to fly from Chicago O'Hare Airport to Key West.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to Key West?

    Only American Airlines offers inflight Wi-Fi service on the Chicago O'Hare Airport to Key West flight route.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Key West?

    The Embraer 170 is the aircraft model that flies most regularly on the Chicago O'Hare Airport to Key West flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to Key West?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago O'Hare Airport and Key West, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Chicago O'Hare Airport to Key West?

    There are nonstop flights from Chicago O'Hare Airport to Key West on a daily basis.

  • Which is the best airline for flights from Chicago to Key West, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Key West are Delta and United Airlines. With an average price for the route of $361 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $482 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Key West?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Key West.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Key West?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Key West from Chicago O'Hare Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Key West?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Key West with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and EYW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Key West?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Key West from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Key West

  • Looking for a cheap flight? 25% of our users found flights on this route for $258 or less one-way and $329 or less round-trip.

Prefer to fly direct from Chicago O'Hare Airport to Key West?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to Key West.
Find which airlines fly direct from Chicago O'Hare Intl Airport to Key West Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Key West

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Key West to Chicago O'Hare Intl

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Reviews of the top 4 airlines serving from O'Hare Intl to Key West

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Key West. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Key West? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8039 reviews
8.5Crew
7.9Comfort
8.1Boarding
7.2Food
7.8Entertainment
Airline reviews

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

8.0 ExcellentG, Jan 2026
ATL - FLL
Read more Delta reviews

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

I've flown two Spirit flights recently - boarding for one was somewhat chaotic, with the board listing the wrong flight and causing much confusion; boarding for the other was very smooth and easy. My seat (for which I did not pay extra) was a bit narrow and without great legroom, but it was fine for a NY-Florida trip and was more than worth the low price I paid. The crew was friendly and one flight landed early and the other was only very slightly delayed. All in all a very good experience.

Your flight crew and boarding area crew need to have microphone use training. They all hold the microphone right up to their mouths, way to close making understanding them almost impossible. The microphone should be held about 3 to 4 inches away from their mouths. This would provide for much better clarity through the PA system. ‘Eating the mic’ DOES NOT work.

It was the first time I flew on that airline and had a very positive experience. Nearly identical to Jetblue which consider the standard of airlines excellence.

A bottled or canned drink, whether water or soda would have been appreciated upon settling in and flying, without being charged for it.

COMMUNICATION!!!! The issue was a crew shortage, which means you knew in advance the issue. Instead of notifying people in advance, we're finding out an hour before the flight it's canceled. You rebooked people to more flights you knew wouldn't get out. You ended by taking part of my party to a completely different state and leaving them there. The next morning, you still have no way to get them to the original destination and they ended up missing an important event. We came out of so much money to check bags multiple times. And on top of all that, the staff in the building seemed to not care and were fairly rude. Overall, just go on and fold and quit making promises to people to get them places when you know you can't. Shoutout to Delta for doing a great job at making it less painful (for those of us who made it).

The flight was cancelled without prior notice. I was inform as I was checking in. No hotel accommodation nor any simple explanation as why it was cancelled.

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Bad experience with gate agent. I asked what group she was boarding. She gave me a face and said, with attitude, group 1. I stood back and waited for my group, group 2 to be called. After an awful lot of people boarded she took the mic and announced, now boarding group 5. The lack of professionalism amongst spirit staff is astounding.

Boarding process was slightly delayed but took an extra long time which caused a 30 minutes delay.

Flight cancelled. Only options are to a different city or wait 2 days for a flight to same destination

Everything you need to know for your flight from O'Hare Intl to Key West

Information on your arrival and departure airports