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ORD - EYW

$109 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 5/31. 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 6/6
Thu 6/13

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 43,707,506 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
12:29 pm - 7:40 pmORD-EYW
6h 11m1 stop
6:00 pm - 11:56 pmEYW-ORD
6h 56m1 stop
$248Delta
Find Deal
Wed, Jun 5 - Wed, Jun 12
12:31 pm - 7:40 pmORD-EYW
6h 09m1 stop
6:10 pm - 11:54 pmEYW-ORD
6h 44m1 stop
$253Delta
Find Deal
Sun, May 26 - Mon, Jun 3
9:32 am - 5:12 pmORD-EYW
6h 40m1 stop
6:10 pm - 11:54 pmEYW-ORD
6h 44m1 stop
$258Delta
Find Deal
Sat, Jun 1 - Tue, Jun 4
9:22 am - 5:05 pmORD-EYW
6h 43m1 stop
2:35 pm - 9:18 pmEYW-ORD
7h 43m1 stop
$262Delta
Find Deal
Fri, Aug 2 - Tue, Aug 6
6:00 am - 1:04 pmORD-EYW
6h 04m1 stop
1:44 pm - 7:28 pmEYW-ORD
6h 44m1 stop
$283American Airlines
Find Deal
Thu, Aug 1 - Mon, Aug 5
7:07 pm - 9:17 amORD-EYW
13h 10m1 stop
9:57 am - 9:55 amEYW-ORD
24h 58m2 stops
Sat, May 25 - Fri, May 31
5:00 am - 1:01 pmORD-EYW
7h 01m1 stop
3:25 pm - 9:25 pmEYW-ORD
7h 00m1 stop
$328American Airlines
Find Deal
Fri, Jun 14 - Wed, Jun 19
6:40 pm - 4:21 pmORD-EYW
20h 41m2 stops
2:41 pm - 10:01 amEYW-ORD
20h 20m2 stops
Sat, Jun 1 - Thu, Jun 6
6:19 pm - 2:40 pmORD-EYW
19h 21m1 stop
11:30 am - 2:15 pmEYW-ORD
27h 45m2 stops
$399United Airlines
Find Deal
Sat, May 25 - Tue, May 28
6:40 pm - 2:25 pmORD-EYW
18h 45m1 stop
11:30 am - 9:21 amEYW-ORD
22h 51m1 stop
$414United Airlines
Find Deal
Tue, Jun 4 - Thu, Jun 6

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 $248 on Delta, followed by American Airlines ($283). One-way flight deals have also been found from as low as $109 on Delta and from $159 on American 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.

Good to know

Low season

September

High season

January

Cheapest flight

$109
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 12% 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 $109 for a one-way ticket and $248 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, oneworld, and Star Alliance 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 $357 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

Top tips for finding a cheap flight from ORD to Key West

  • Looking for a cheap flight? 25% of our users found flights on this route for $303 or less one-way and $406 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 9147 reviews
7.3Food
8.6Crew
7.3Entertainment
8.2Boarding
7.9Comfort
Airline reviews

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

6.0 GoodAnonymous, May 2024SEA - HNL
Read more about Alaska Airlines reviews

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

The flight was great. The pilot was great. It was really annoying that the staff had facemasks on. Hard to hear what they’re saying when a mask is covering their mouth. I enjoyed the flight, but there was a crying baby in front of me. You guys should offer flights baby free. I would be very into that me and the person next to me discussed how they should make free flights for all of us that don’t have kids. I wouldn’t mind paying extra to not have to deal with the smell of a dirty diaper or screaming of a child. Also, if they had a separate room, the babies could be sent to the back with a curtain or something muddle the horrible sounds.

Smooth. Courteous. Fun. One problem: the wheels on my checked roller back were broken when I picked up baggage at destination. Must have happened during flight baggage handling but I don’t know where.

Staff very helpful and friendly, in flight entertainment poor. Flight left late and thus arrived 20 minutes late to final destination.

Ground crew was great in Austin, flight crew left a lot to be desired. Not particularly friendly, helpful or nice.

Everything was fine -- on time, clear, clean. I don't want to pay extra for in-flight wi-fi

First time flying with Alaska and the staff were All professional from checkin to departure! I do plan to book more flights with Alaska. Thanks

The flight was delayed because the pilots had not arrived on their previous flight yet. The flight was 100% full so it was pretty crowded. I miss having the screens on the back of the seats. It would be great if the Alaska planes had the clip so you can put your phone or tablet on the back of the seat in front of you to not strain your neck. Everything else was very smooth.

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

It was fine since it ensure we went to our destination in time.

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.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

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.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

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.

Regarding the boarding: it needs more efforts to make it more convenient

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.
5/31Fri
1 stopDelta
6h 11mORD-EYW
$109
6/5Wed
2 stops
21h 29mORD-EYW
$127
6/5Wed
3 stops
28h 13mORD-EYW
$140
9/2Mon
1 stopAmerican Airlines
7h 55mORD-EYW
$159
9/2Mon
1 stopDelta
4h 49mORD-EYW
$164
5/25Sat
2 stops
20h 51mORD-EYW
$169
5/25Sat
1 stopUnited Airlines
19h 21mORD-EYW
$240
5/25Sat
3 stops
32h 01mORD-EYW
$243
5/14Tue
1 stopUnited Airlines
18h 46mORD-EYW
$246
6/5Wed
1 stopAmerican Airlines
5h 44mORD-EYW
$258

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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.
5/11Sat
multi-stopAmerican Airlines
5h 13mORD-EYW
5/14Tue
multi-stopAmerican Airlines
8h 18mEYW-ORD
$435
5/12Sun
multi-stopAmerican Airlines
5h 06mORD-EYW
5/18Sat
multi-stopAmerican Airlines
8h 56mEYW-ORD
$436
5/12Sun
multi-stopAmerican Airlines
6h 48mORD-EYW
5/18Sat
multi-stopAmerican Airlines
7h 02mEYW-ORD
$441
5/9Thu
multi-stopAmerican Airlines
6h 38mORD-EYW
5/12Sun
multi-stopAmerican Airlines
6h 49mEYW-ORD
$485
5/11Sat
multi-stopUnited Airlines
7h 12mORD-EYW
5/14Tue
multi-stopUnited Airlines
12h 00mEYW-ORD
$524
5/12Sun
multi-stopUnited Airlines
9h 25mORD-EYW
5/18Sat
multi-stopUnited Airlines
13h 05mEYW-ORD
$552
5/11Sat
multi-stopUnited Airlines
9h 40mORD-EYW
5/14Tue
multi-stopUnited Airlines
12h 00mEYW-ORD
$584
5/12Sun
multi-stopUnited Airlines
9h 25mORD-EYW
5/18Sat
multi-stopUnited Airlines
13h 05mEYW-ORD
$657
5/9Thu
multi-stopAmerican Airlines
4h 46mORD-EYW
5/12Sun
multi-stopAmerican Airlines
9h 00mEYW-ORD
$680
5/9Thu
multi-stopAmerican Airlines
8h 06mORD-EYW
5/12Sun
multi-stopAmerican Airlines
9h 11mEYW-ORD
$685

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Chicago O'Hare Airport - Key West Flights

Departure:

Chicago O'Hare Airport (undefined)United States

Destination:

Key West (EYW)United States

Return flight deals:

Key West - Chicago O'Hare Airport

Cabin classes:

$1,058
$1,053
$754
$321