Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

ORD - EYW

$144 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 7/11. 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
0 bags
Thu 7/11
Thu 7/18

Search 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
In the last 7 days travelers have searched 44,212,782 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
6:00 am - 1:35 pmORD-EYW
6h 35m1 stop
7:23 am - 11:12 amEYW-ORD
4h 49m1 stop
$232Delta
Find Deal
Tue, Aug 27 - Sun, Sep 1
6:16 pm - 9:09 amORD-EYW
13h 53m1 stop
5:30 pm - 9:14 amEYW-ORD
16h 44m2 stops
Wed, Jun 26 - Wed, Jul 10
6:16 pm - 9:09 amORD-EYW
13h 53m1 stop
5:30 pm - 9:14 amEYW-ORD
16h 44m2 stops
Wed, Jun 26 - Wed, Jul 24
6:00 am - 1:46 pmORD-EYW
6h 46m1 stop
7:25 am - 12:34 pmEYW-ORD
6h 09m1 stop
$248Delta
Find Deal
Mon, Sep 9 - Sat, Sep 14
6:00 am - 11:47 amORD-EYW
4h 47m1 stop
7:23 am - 11:12 amEYW-ORD
4h 49m1 stop
$263Delta
Find Deal
Tue, Aug 27 - Sun, Sep 1
6:00 am - 11:47 amORD-EYW
4h 47m1 stop
12:42 pm - 4:43 pmEYW-ORD
5h 01m1 stop
$268Delta
Find Deal
Sat, Jul 27 - Fri, Aug 2
9:45 am - 4:29 pmORD-EYW
5h 44m1 stop
12:05 pm - 7:27 pmEYW-ORD
8h 22m1 stop
$273American Airlines
Find Deal
Sun, Jun 30 - Thu, Jul 4
5:07 am - 2:06 pmORD-EYW
7h 59m2 stops
1:41 pm - 9:25 pmEYW-ORD
8h 44m1 stop
$278American Airlines
Find Deal
Sun, Jun 30 - Thu, Jul 4
10:55 am - 2:45 pmORD-EYW
26h 50m1 stop
3:23 pm - 9:13 pmEYW-ORD
6h 50m1 stop
$330United Airlines
Find Deal
Thu, Sep 12 - Tue, Sep 17
6:40 pm - 2:35 pmORD-EYW
18h 55m1 stop
11:20 am - 9:51 amEYW-ORD
23h 31m1 stop
$331United Airlines
Find Deal
Wed, Aug 14 - Sun, Aug 18

Flights from O'Hare Intl to Key West - Travel Insights & Trends

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 flights from Chicago O'Hare Intl Airport to Key West clicked on KAYAK for each day over the last 12 months.
For Chicago O'Hare Airport to Key West, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Key West back to Chicago O'Hare Airport, the best deals are generally found on Wednesday, with Saturday being the most expensive.

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 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 August, where tickets cost $310 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $529 and $518 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
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 60 days before departure.

Which airlines provide the cheapest flights from Chicago O'Hare Airport to Key West?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago O'Hare Airport to Key West found by KAYAK users in the last 72 hours was for $232 on Delta, followed by American Airlines ($273). One-way flight deals have also been found from as low as $169 on Delta and from $171 on United Airlines.

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Key West?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are First, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago O'Hare Airport to Key West take?

Flying to Key West from Chicago O'Hare Airport requires at least one layover, as there are no direct flights for this route. The shortest flight duration is 3h 10m.

Good to know

Low season

September

High season

January

Cheapest flight

$144
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 13% 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 $144 for a one-way ticket and $232 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?

    American Airlines, and PSA Airlines offer 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.

  • What is the most popular layover when flying to Key West from Chicago O'Hare Airport?

    Charlotte is the most popular layover city among KAYAK users traveling from Chicago O'Hare Airport to Key West.

  • 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 $364 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 $469 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.

See more FAQs

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 $341 or less round-trip.

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.
8.0
Alaska AirlinesOverall score based on 9267 reviews
7.3Food
7.3Entertainment
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

First class only upgrades seat width. The bottom cushion of the seat sloped forward so much that I was constantly sliding out of my seat. The meal was awful, granola and dried fruit? Seriously, for what I paid to upgrade? I can bring my own sawdust and rotten fruit for a whole lot less. Priority boarding is great except when you have a hundred economy passengers stranding in the aisle slamming you in the face with their enormous carry ons and smelly asses right under your nose. I want my money back for that leg of my trip. It wasn’t worth the money for such a minimal upgrade.

4.0 OkayAnonymous, Jun 2024MKE - SEA
Read more about Alaska Airlines reviews

First class only upgrades seat width. The bottom cushion of the seat sloped forward so much that I was constantly sliding out of my seat. The meal was awful, granola and dried fruit? Seriously, for what I paid to upgrade? I can bring my own sawdust and rotten fruit for a whole lot less. Priority boarding is great except when you have a hundred economy passengers stranding in the aisle slamming you in the face with their enormous carry ons and smelly asses right under your nose. I want my money back for that leg of my trip. It wasn’t worth the money for such a minimal upgrade.

I had never flown Alaska Airlines before. I’ll definitely use them again. Seats were comfortable and roomier than expected.

Seats lack shoulder and elbow room. The lady next to me was short and slightly heavy with knee problems, she kept jabbing me with her elbow while playing her game on her phone for 2 hours, the duration of the whole flight. It was frustrating and annoying! I was in the middle seat, there was no space to adjust to avoid her arm jabbing me.

I was in second from last seat. My luggage was in row 15. I asked the stewardess if I could move up before the plane lands. There were 3 empty rows. She went on to explain to me, how no one was sitting there when the plane took off and there was no education on the exit doors. Blah, blah, blah. I said ok, S he kept over explaining to me. So whatever if that’s the rules. She went in the back to the other 2 stewards to tell them the entire conversation I just had with her. Not only could I hear her so could all the back rows of the plane. This was very unprofessional and inappropriate.

Soda cans were mini-size; snacks were teeny. Options for entertainment on trans-continent flights were bad - no seat screens and no way to support device (as seen on other airlines) so had to hold device in position. Just overall, not good (compared to United)

I like the big picture of the Eskimo on the tail of the plane.

The crew members were wonderful. When we encountered a little turbulence, the pilots let us know and provided an estimate of how long it would last. Another nice amenity: every seat has AC power outlets and USB ports. It was a 6-hour flight, which seems a bit much for a single-aisle jet: over 200 passengers with access to only 3 restrooms (assuming you time it right and won't be blocked in by beverage carts); food is mediocre, over-priced, and (if you failed to reserve a meal ahead of time) the flight attendants have to process food/meal sales in the aisle. To access any entertainment, you must use your own device to log on to the plane's wi-fi (or bring your own entertainment).

The crews on Alaska Airlines are really wonderful. They clearly know how to treat passengers with kindness and respect. During my trip, I discovered that my upgraded seat had been changed when reviewing my electronic boarding pass. When I questioned the change at the gate, the two staff members acknowledged that the change was odd, checked on their computer, and confirmed that I still had my upgraded seat (i.e., the electronic boarding pass was incorrect). I was impressed by how they seemed to be "in my corner" from the start, quickly investigated, and provided me with a paper boarding pass with the correct information "just in case." All that said, I was a bit disappointed that Alaska Airlines uses single-aisle jets with only four restrooms (3 at the back of the plane, one at the front (ostensibly reserved for crew and first class travelers). I would understand for short flights, but for a 6-hour flight from Seattle to Honolulu...really? I will stick with Hawaiian Airlines from now on.

Seats are more spacious than other airlines that have you packed like sardines.

Barbara at JFK terminal for Alaska was very helpful in retrieving our boarding passes for our connecting and quite pleasant!! Thanks

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We sat on the plane for 1 hour because the airline was short handed could not be unloading.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Book cheap flights from Chicago to Key West

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Key West found on KAYAK in the last 72 hours.
7/11Thu
2 stops
19h 05mORD-EYW
$144
7/4Thu
2 stops
20h 40mORD-EYW
$149
7/4Thu
2 stops
20h 40mORD-EYW
$166
7/4Thu
1 stopDelta
6h 38mORD-EYW
$169
9/16Mon
1 stopUnited Airlines
26h 50mORD-EYW
$171
7/11Thu
3 stops
20h 51mORD-EYW
$172
9/16Mon
2 stopsUnited Airlines
21h 20mORD-EYW
$239
11/6Wed
nonstopAmerican Airlines
3h 12mORD-EYW
$250
11/6Wed
1 stopDelta
6h 39mORD-EYW
$254
11/6Wed
nonstopAmerican Airlines
3h 12mORD-EYW
$284

Search by stops

Search by airline

Search by price

Last minute flights from O'Hare Intl to Key West

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Key West that are departing in the next 10 days.
6/14Fri
multi-stopAmerican Airlines
5h 59mORD-EYW
6/17Mon
multi-stopAmerican Airlines
7h 44mEYW-ORD
$438
6/14Fri
multi-stopAmerican Airlines
7h 25mORD-EYW
6/17Mon
multi-stopAmerican Airlines
5h 38mEYW-ORD
$443
6/14Fri
multi-stopAmerican Airlines
7h 59mORD-EYW
6/17Mon
multi-stopAmerican Airlines
7h 57mEYW-ORD
$493
6/14Fri
multi-stopAmerican Airlines
9h 42mORD-EYW
6/17Mon
multi-stopAmerican Airlines
9h 12mEYW-ORD
$528
6/15Sat
multi-stopAmerican Airlines
5h 55mORD-EYW
6/22Sat
multi-stopAmerican Airlines
5h 24mEYW-ORD
$538
6/15Sat
multi-stopAmerican Airlines
9h 11mORD-EYW
6/22Sat
multi-stopAmerican Airlines
7h 49mEYW-ORD
$543
6/14Fri
multi-stopAmerican Airlines
8h 29mORD-EYW
6/17Mon
multi-stopAmerican Airlines
8h 12mEYW-ORD
$578
6/15Sat
multi-stopAmerican Airlines
10h 59mORD-EYW
6/22Sat
multi-stopAmerican Airlines
9h 15mEYW-ORD
$683
6/13Thu
multi-stopDelta
5h 15mORD-EYW
6/13Thu
multi-stopDelta
6h 56mEYW-ORD
$1,028
6/13Thu
multi-stopAmerican Airlines
7h 25mORD-EYW
6/13Thu
multi-stopAmerican Airlines
7h 59mEYW-ORD
$1,038

Search by stops

Search by airline

Search by price

Chicago O'Hare Airport - Key West Flights

Departure:

Chicago O'Hare Airport (ORD)United States

Destination:

Key West (EYW)United States

Return flight deals:

Key West - Chicago O'Hare Airport

Cabin classes:

$1,058
$1,053
$754
$229