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EYW - ORD

$220 Find cheap flights from Key West to Chicago O'Hare Intl Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to O'Hare Intl departing on 5/21. 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
Sat 5/25
Sat 6/1

Search hundreds of travel sites at once for deals on flights to Chicago O'Hare Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Chicago, 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 Key West to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,979,812 times on KAYAK, and here is why:

Save 22% 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.

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to O'Hare Intl 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
5:09 pm - 11:59 pmEYW-ORD
7h 50m1 stop
8:30 am - 5:25 pmORD-EYW
7h 55m1 stop
$245American Airlines
Find Deal
Wed, May 22 - Wed, May 29
5:04 pm - 10:34 pmEYW-ORD
6h 30m1 stop
6:02 am - 1:01 pmORD-EYW
5h 59m1 stop
$248American Airlines
Find Deal
Wed, Jun 5 - Wed, Jun 26
11:43 am - 3:36 pmEYW-ORD
4h 53m1 stop
5:30 am - 1:05 pmORD-EYW
6h 35m2 stops
$250American Airlines
Find Deal
Tue, Aug 13 - Tue, Aug 27
6:00 pm - 11:59 pmEYW-ORD
6h 59m1 stop
6:00 am - 11:44 amORD-EYW
4h 44m1 stop
$268Delta
Find Deal
Fri, Jul 19 - Mon, Jul 22
3:25 pm - 11:41 pmEYW-ORD
9h 16m1 stop
5:30 am - 12:06 pmORD-EYW
5h 36m1 stop
$281American Airlines
Find Deal
Wed, Jun 19 - Sun, Jun 23
11:25 am - 11:30 pmEYW-ORD
13h 05m2 stops
7:00 am - 5:24 pmORD-EYW
9h 24m1 stop
$443United Airlines
Find Deal
Sat, May 11 - Tue, May 14
12:30 pm - 11:30 pmEYW-ORD
12h 00m2 stops
6:00 am - 2:09 pmORD-EYW
7h 09m1 stop
$444United Airlines
Find Deal
Wed, May 22 - Wed, May 29
11:25 am - 9:29 amEYW-ORD
23h 04m1 stop
7:00 am - 5:24 pmORD-EYW
9h 24m1 stop
$478United Airlines
Find Deal
Sat, May 11 - Tue, May 14
6:10 pm - 11:58 pmEYW-ORD
6h 48m1 stop
5:40 am - 1:00 pmORD-EYW
6h 20m1 stop
$483Delta
Find Deal
Sat, May 11 - Tue, May 14
7:25 am - 5:28 pmEYW-ORD
11h 03m2 stops
8:30 am - 7:40 pmORD-EYW
10h 10m2 stops
$1,372Delta
Find Deal
Wed, Jun 19 - Sun, Jun 23

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

Get data-powered insights and trends into flights from Key West to O'Hare Intl 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 Key West to Chicago O'Hare Airport?

The average price of all flights from Key West to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
When flying from Key West to Chicago O'Hare Airport, you should consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Key West, you’ll find the best rates on Tuesdays and the most expensive ones on Thursdays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Key West to Chicago O'Hare Intl Airport, 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 Key West to Chicago O'Hare Intl Airport is September, where tickets cost $291 on average. On the other hand, the most expensive months are June and March, where the average cost of tickets is $617 and $585 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Key West to Chicago O'Hare Intl Airport, 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 Key West to Chicago O'Hare Intl Airport, you should book around 4 days before departure. For the absolute cheapest price, our data suggests you should book 39 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Key West to Chicago O'Hare Airport found by KAYAK users in the last 72 hours was for $245 on American Airlines, followed by Delta ($268). One-way flight deals have also been found from as low as $220 on United Airlines and from $253 on American Airlines.

Which airlines fly non-stop between Key West and Chicago O'Hare Intl Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Key West to Chicago O'Hare Intl Airport.
There is just one airline that flies from Key West to Chicago O'Hare Intl Airport direct and that is American Airlines. The best one-way deal found from American Airlines for the route is $224.

How many flights are there between Key West and Chicago O'Hare Intl Airport per day?

There is a maximum of 1 nonstop flight a day that takes off from Key West and lands in Chicago O'Hare Intl Airport, with an average flight time of 3h 25m. The most common departure time is 1:00 pm and most flights take off in the afternoon. Each week, there are 7 flights.

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

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 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from Key West to Chicago O'Hare Airport?

Early birds can take the earliest flight from Key West at 1:09 pm and will be landing in Chicago O'Hare Intl Airport at 3:34 pm.

What’s the latest departure time from Key West to Chicago O'Hare Airport?

If you prefer to fly at night, the latest flight from Key West to Chicago O'Hare Intl Airport jets off at 1:09 pm and lands at 3:34 pm.

Good to know

Low season

June

High season

October

Cheapest flight

$220
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly with an average 6% increase in price.
Flight from Key West to Chicago O'Hare Airport

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

Are your dates flexible? Find out the best times to travel from Key West to O'Hare Intl 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 Key West to Chicago O'Hare Airport flights

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

    In the last 3 days, the lowest price for a flight from Key West to Chicago O'Hare Intl Airport was $220 for a one-way ticket and $245 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

    The Boeing 737-700 is the aircraft model that flies most regularly on the Key West to Chicago O'Hare Airport flight route.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Key West to Chicago are Delta and United Airlines. With an average price for the route of $441 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 $582 and an overall rating of 7.4.

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

    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 Key West to Chicago O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Key West 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 Key West to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport with an airline and back to Key West with another airline. Booking your flights between Key West and ORD 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 Key West to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport from Key West 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 EYW to Chicago O'Hare Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $332 or less one-way and $391 or less round-trip.

Prefer to fly non-stop from Key West to Chicago O'Hare Airport?

Find which airlines fly direct from Key West to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Key West to Chicago O'Hare Intl

Monday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Tuesday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Wednesday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Thursday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Friday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Saturday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Sunday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Key West

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights
See more direct flights

Top 3 airlines serving from Key West to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Key West to Chicago. 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 Key West to O'Hare Intl? 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 10975 reviews
8.6crew
7.9comfort
8.0entertainment
8.2boarding
7.4food
Airline reviews

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

10.0 ExcellentAnonymous, Apr 2024PNS - ATL
Read more about Delta reviews

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

Flight was on time, the staff was personable & professional, & the plane arrived on time.

Flight was great. DELTA did a fantastic job! FLL airport was chaotic!

You lost my luggage!!! How frustrating!!! Now they can’t find one of our bags!!!! I really don’t have time for this!!!

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The flights from Ottawa to Albuquerque went smoothly enough though on on flight they didn't have how water for coffee or tea and on another there there was no ice. The return flights from Albuquerque were delayed by mechanical problems on both flights. Ottawa was a ground crew maintenance issue.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Book cheap flights from Key West to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Key West to Chicago found on KAYAK in the last 72 hours.
5/21Tue
1 stopUnited Airlines
22h 59mEYW-ORD
$220
5/15Wed
2 stopsUnited Airlines
13h 00mEYW-ORD
$225
5/15Wed
1 stopAmerican Airlines
8h 18mEYW-ORD
$253
5/26Sun
1 stopAmerican Airlines
8h 56mEYW-ORD
$254
6/4Tue
2 stopsUnited Airlines
28h 10mEYW-ORD
$283
6/10Mon
1 stopAmerican Airlines
7h 00mEYW-ORD
$288
6/10Mon
2 stopsUnited Airlines
27h 30mEYW-ORD
$375
5/27Mon
1 stopAmerican Airlines
7h 50mEYW-ORD
$387
7/8Mon
2 stopsUnited Airlines
22h 30mEYW-ORD
$393
5/6Mon
1 stopAmerican Airlines
5h 20mEYW-ORD
$418

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Last minute flights from Key West to O'Hare Intl

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 Key West to Chicago that are departing in the next 10 days.
4/30Tue
multi-stopDelta
6h 23mEYW-ORD
5/4Sat
multi-stopDelta
6h 10mORD-EYW
$428
4/26Fri
nonstopAmerican Airlines
3h 25mEYW-ORD
4/30Tue
nonstopAmerican Airlines
3h 14mORD-EYW
$459
4/26Fri
multi-stopAmerican Airlines
6h 11mEYW-ORD
4/30Tue
nonstopAmerican Airlines
3h 14mORD-EYW
$467
4/26Fri
multi-stopAmerican Airlines
6h 11mEYW-ORD
4/30Tue
multi-stopAmerican Airlines
5h 10mORD-EYW
$475
4/30Tue
nonstopUnited Airlines
3h 28mEYW-ORD
5/4Sat
multi-stopUnited Airlines
7h 12mORD-EYW
$498
4/30Tue
multi-stopUnited Airlines
8h 56mEYW-ORD
5/4Sat
multi-stopUnited Airlines
9h 24mORD-EYW
$513
4/26Fri
multi-stopUnited Airlines
7h 32mEYW-ORD
4/30Tue
multi-stopUnited Airlines
9h 50mORD-EYW
$563
4/26Fri
multi-stopUnited Airlines
8h 25mEYW-ORD
4/30Tue
multi-stopUnited Airlines
8h 25mORD-EYW
$568

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Key West - Chicago O'Hare Airport Flights

Departure:

Key West (EYW)United States

Destination:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Chicago O'Hare Airport - Key West

Cabin classes:

$1,105
$1,198
$714
$267