ORD - EYW

$101 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 10/5. 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

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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Flights 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

Mon, Dec 15 - Mon, Dec 22
United Airlines Logo
10:55 am - 3:14 pmORD-EYW
3h 19mnonstop
United Airlines Logo
4:05 pm - 6:30 pmEYW-ORD
3h 25mnonstop
$249United Airlines
Find Deal
Tue, Dec 16 - Sun, Dec 21
United Airlines Logo
6:00 am - 2:04 pmORD-EYW
7h 04m1 stop
United Airlines Logo
4:05 pm - 6:30 pmEYW-ORD
3h 25mnonstop
$259United Airlines
Find Deal
Sat, Aug 16 - Sat, Aug 23
Delta Logo
1:30 pm - 8:12 pmORD-EYW
5h 42m1 stop
Delta Logo
7:00 am - 12:17 pmEYW-ORD
6h 17m1 stop
$269Delta
Find Deal
Tue, Jul 15 - Fri, Jul 25
Delta Logo
1:26 pm - 7:49 pmORD-EYW
5h 23m1 stop
Delta Logo
6:27 pm - 12:09 amEYW-ORD
6h 42m1 stop
$289Delta
Find Deal
Mon, Dec 15 - Mon, Dec 22
United Airlines Logo
6:00 am - 2:04 pmORD-EYW
7h 04m1 stop
United Airlines Logo
4:05 pm - 6:30 pmEYW-ORD
3h 25mnonstop
$302United Airlines
Find Deal
Tue, Nov 4 - Sat, Nov 8
American Airlines Logo
8:00 am - 12:16 pmORD-EYW
3h 16mnonstop
American Airlines Logo
2:00 pm - 7:33 pmEYW-ORD
6h 33m1 stop
$313American Airlines
Find Deal
Wed, Nov 12 - Sat, Nov 15
Delta Logo
9:30 am - 5:12 pmORD-EYW
6h 42m1 stop
Delta Logo
1:30 pm - 7:17 pmEYW-ORD
6h 47m1 stop
$320Delta
Find Deal
Sat, Aug 2 - Wed, Aug 6
American Airlines Logo
5:00 am - 1:50 pmORD-EYW
7h 50m1 stop
American Airlines Logo
5:02 pm - 10:49 pmEYW-ORD
6h 47m1 stop
$323American Airlines
Find Deal
Sat, Aug 2 - Tue, Aug 5
 Logo
11:21 am - 11:41 amORD-EYW
23h 20m2 stops
 Logo
10:02 am - 7:04 amEYW-ORD
22h 02m2 stops
Sat, Aug 2 - Tue, Aug 5
 Logo
11:21 am - 11:41 amORD-EYW
23h 20m2 stops
 Logo
10:02 am - 7:26 pmEYW-ORD
10h 24m1 stop
Expert advice

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

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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.

Read more about ORDby Stefanie Waldek
EYW

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

Read more about EYWby Paul Rubio
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
Useful Info

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 Thursdays 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 September, 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 $536 and $501 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 $905 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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonSeptember
High seasonJanuary
Cheapest flight$101
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 9% lower on average.
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 $101 for a one-way ticket and $249 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?

    oneworld is the only airline alliance operating flights between Chicago O'Hare Airport and Key West.

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

    You can catch a nonstop flight from Chicago O'Hare Airport to Key West on Saturday.

  • 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 $337 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $477 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 $361 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

Saturday

American Airlines

American Airlines

See more direct flights

Direct returns

Key West to Chicago O'Hare Intl

Saturday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

See more direct flights

Reviews of the top 3 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.
8.0
DeltaOverall score based on 7982 reviews
7.9Comfort
7.3Food
8.5Crew
8.2Boarding
7.9Entertainment
Airline reviews

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

4.0 OkayMrs., Jul 2025LAX - RDU
Read more Delta reviews

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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

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