ORD - EYW

$140 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 8/5. 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, 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$319
Typical prices: $498-$289
American Airlines
Tue 7/7Tue 7/14
ORD - EYW • Non-stop
Cheapest one-way
$140
Multiple Airlines
Wed 8/5
ORD - EYW • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Basic Economy saves money, while Main Cabin Extra adds early boarding.
United Economy Plus adds legroom; buy Priority Boarding for overhead bin space.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $319 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 3h 24m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $420 (round-trip)
Shortest trip • 5h 15m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 9% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 16% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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Start a new search
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

Tue, Jul 7 - Tue, Jul 14
American Airlines Logo
11:22 am - 3:43 pm
ORD
-
EYW
3h 21mnonstop
American Airlines Logo
4:18 pm - 7:06 pm
EYW
-
ORD
3h 48mnonstop
$319American Airlines
Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
5:30 pm - 11:27 am
ORD
-
EYW
16h 57m
1 stop
Multiple Airlines Logo
12:07 pm - 11:14 pm
EYW
-
ORD
12h 07m
1 stop
$322Multiple Airlines
Wed, Jul 22 - Fri, Jul 31
Multiple Airlines Logo
1:50 pm - 11:07 am
ORD
-
EYW
44h 17m
2 stops
Multiple Airlines Logo
12:07 pm - 11:10 pm
EYW
-
ORD
12h 03m
1 stop
$323Multiple Airlines
Thu, Aug 27 - Thu, Sep 3
Multiple Airlines Logo
5:30 pm - 11:27 am
ORD
-
EYW
16h 57m
1 stop
Multiple Airlines Logo
12:05 pm - 11:14 pm
EYW
-
ORD
12h 09m
1 stop
$327Multiple Airlines
Mon, Jul 20 - Mon, Jul 27
American Airlines Logo
5:07 am - 12:14 pm
ORD
-
EYW
6h 07m
1 stop
American Airlines Logo
7:33 pm - 12:01 am
EYW
-
ORD
5h 28m
1 stop
$328American Airlines
Thu, Aug 13 - Tue, Aug 18
American Airlines Logo
11:59 am - 4:18 pm
ORD
-
EYW
3h 19mnonstop
American Airlines Logo
1:50 pm - 7:46 pm
EYW
-
ORD
6h 56m
1 stop
$329American Airlines
Sat, Sep 12 - Fri, Sep 25
Multiple Airlines Logo
4:49 pm - 10:19 am
ORD
-
EYW
16h 30m
1 stop
Multiple Airlines Logo
12:59 pm - 7:44 pm
EYW
-
ORD
31h 45m
2 stops
$334Multiple Airlines
Sat, Sep 12 - Wed, Sep 16
Multiple Airlines Logo
4:49 pm - 10:19 am
ORD
-
EYW
16h 30m
1 stop
Multiple Airlines Logo
10:04 am - 3:26 pm
EYW
-
ORD
30h 22m
2 stops
$337Multiple Airlines
Thu, Aug 13 - Mon, Aug 17
Delta Logo
1:50 pm - 7:57 pm
ORD
-
EYW
5h 07m
1 stop
Delta Logo
7:40 am - 2:09 pm
EYW
-
ORD
7h 29m
1 stop
$339Delta
Wed, Jul 1 - Tue, Jul 7
American Airlines Logo
11:00 am - 3:25 pm
ORD
-
EYW
3h 25mnonstop
American Airlines Logo
1:01 pm - 5:39 pm
EYW
-
ORD
5h 38m
1 stop
$346American 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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Key West?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Key West departing in July.

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 Sundays if you are looking for the best rates. For your return to Chicago O'Hare Airport, you’ll find the best rates on Wednesdays and the most expensive ones on Mondays.

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 May, where tickets cost $361 (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 $540 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.

No, with an average price for the route of $439, prices are generally cheapest when you fly direct.

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 2 weeks before departure, which saves you about 9% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 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.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

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.

Paul Rubio

Paul Rubio

Expert on EYW

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.

Good to know

Low seasonAugust
Cheapest flight$140
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 16% 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 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Key West was $140 for a one-way ticket and $319 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 $368 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 $415 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 $188 or less one-way and $349 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 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.
7.9
DeltaOverall score based on 8396 reviews
7.2Food
8.1Boarding
7.8Entertainment
7.8Comfort
8.5Crew
Airline reviews

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

8.0 ExcellentAnonymous, Jun 2026
ATL - GNV
Read more Delta reviews

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Very easy to use and convenient, you can perform any action within the same portal

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

Okay considering we had weather delays which the Pilot notified us of immediately!

N Everything was perfect from boarding to assistance to baggage in Tampa

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

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

Information on your arrival and departure airports