EYW - CHI

$99 Find Cheap Flights from Key West to Chicago

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 Chicago departing on 3/26. 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.
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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
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Cheap Flight Deals from Key West to Chicago (EYW-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Chicago 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.

Recent round-trip flight deals from Key West to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Key West to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
4:04 pm - 6:39 pmEYW-ORD
3h 35mnonstop
10:59 am - 3:04 pmORD-EYW
3h 05mnonstop
$229United Airlines
Find Deal
Fri, Apr 25 - Tue, Apr 29
12:56 pm - 3:33 pmEYW-ORD
3h 37mnonstop
8:05 am - 12:22 pmORD-EYW
3h 17mnonstop
$303American Airlines
Find Deal
Wed, Apr 16 - Tue, Apr 22
11:39 am - 6:16 pmEYW-ORD
7h 37m1 stop
8:05 am - 12:22 pmORD-EYW
3h 17mnonstop
$312American Airlines
Find Deal
Fri, Apr 25 - Tue, Apr 29
8:00 am - 2:15 pmEYW-ORD
7h 15m1 stop
8:05 am - 12:22 pmORD-EYW
3h 17mnonstop
$313American Airlines
Find Deal
Wed, Apr 16 - Tue, Apr 22
7:00 am - 12:03 pmEYW-MDW
6h 03m1 stop
12:48 pm - 8:30 pmMDW-EYW
6h 42m1 stop
$323Delta
Find Deal
Wed, Apr 16 - Tue, Apr 22
3:06 pm - 7:29 pmEYW-ORD
5h 23m1 stop
5:10 am - 12:06 pmORD-EYW
5h 56m1 stop
$323American Airlines
Find Deal
Wed, Apr 16 - Tue, Apr 22
3:57 pm - 11:24 pmEYW-ORD
8h 27m1 stop
12:00 pm - 6:45 pmORD-EYW
5h 45m1 stop
$326American Airlines
Find Deal
Thu, Apr 3 - Wed, Apr 9
4:04 pm - 6:39 pmEYW-ORD
3h 35mnonstop
10:59 am - 3:04 pmORD-EYW
3h 05mnonstop
$358United Airlines
Find Deal
Thu, Apr 3 - Wed, Apr 9
7:29 pm - 11:54 pmEYW-ORD
5h 25m1 stop
8:00 am - 3:18 pmORD-EYW
6h 18m1 stop
$359American Airlines
Find Deal
Fri, Apr 25 - Tue, Apr 29
6:15 pm - 11:56 pmEYW-ORD
6h 41m1 stop
5:45 am - 11:35 amORD-EYW
4h 50m1 stop
$405Delta
Find Deal
Sat, Mar 15 - Tue, Mar 18

Expert advice for your flight from Key West to Chicago

Our travel pros reveal their best tips for your Key West to Chicago journey.
Airlines
American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks on longer flights.


Basic Economy offers low fares but includes restrictions like late boarding and no seat assignment.

United Airlines

United's Economy Plus offers up to six inches more legroom than standard economy seats.


Purchase Priority Boarding to ensure overhead bin space and avoid gate-checking your carry-on.

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

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

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.

Flights from Key West to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Key West to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Key West to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Key West to Chicago.
Our data shows that the cheapest route for a return flight from Key West to Chicago cost $229 and was between Key West (EYW) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $229.

What’s the cheapest day of the week to fly from Key West to Chicago?

The average price of all round-trip flights from Key West to Chicago clicked on KAYAK for each day over the last 12 months.
When flying from Key West to Chicago, you should consider leaving on a Thursday and avoid Sundays 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?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Key West to Chicago, 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 is August, where tickets cost $294 (return) on average. On the other hand, the most expensive months are February and September, where the average cost of round-trip tickets is $536 and $460 respectively.

Can I save money by flying with a layover from Key West to Chicago?

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 $378, prices are generally cheapest when you fly direct.

Good to know

Low season

February

High season

December

Cheapest flight

$99
Best time to beat the crowds but there is an average 38% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Key West to Chicago O'Hare Airport

When to book flights from Key West to Chicago

Are your dates flexible? Find out the best times to travel from Key West to Chicago 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 flights from Key West to Chicago

  • What is the cheapest flight from Key West to Chicago?

    In the last 3 days, the lowest price for a flight from Key West to Chicago was $99 for a one-way ticket and $229 for a round-trip.

  • Do I need a passport to fly between Key West and Chicago?

    A passport is not required to fly from Key West to Chicago.

  • Which airports will I be using when flying from Key West to Chicago?

    When flying out of Key West you will be using Key West. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

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

  • Which aircraft models fly most regularly from Key West to Chicago?

    The Embraer 170 is the aircraft model that flies most regularly on the Key West to Chicago flight route.

  • Which airline alliances offer flights from Key West to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Key West and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Key West to Chicago?

    There are nonstop flights from Key West to Chicago 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 $377 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 $406 and an overall rating of 7.4.

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 with an airline and back to Key West with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Chicago?

    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 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

KAYAK’s top tips for finding a cheap flight from Key West to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $158 or less one-way and $418 or less round-trip.

Prefer to fly direct from Key West to Chicago?

Find which airlines fly direct from Key West Airport to Chicago, which days they fly and book direct flights.

Direct departures

Key West to Chicago

Monday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Tuesday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Wednesday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Thursday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Friday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Saturday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Sunday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

See more direct flights

Direct returns

Chicago to Key West

Monday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Tuesday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Wednesday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Thursday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Friday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Saturday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Sunday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

See more direct flights
See more direct flights

Top 3 airlines serving from Key West to Chicago

 
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 Chicago? 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 8061 reviews
8.2Boarding
8.0Comfort
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

8.0 ExcellentAnonymous, Feb 2025EYW - ATL
Read more Delta reviews

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Great - This was the last flight before hurricane closures and did a quick turnaround to get the plane heading north. Much appreciated.

I liked the screens in the seat headrest with movies to watch. I didn’t like being forced to check my carryon bag and being told there wasn’t room for my bag - when there were 5 bins sitting empty on takeoff. I didn’t like the “I don’t give a fig” attitude of the flight attendants and the delta gate attendants when I asked why they decided to put me out. They gave me a 1800 number to call but I can’t get a live person on the phone. Customer service is non existent. My business must not be that important to them.

It was not in Delta's control, but when we landed, we ended up parking at the wrong gate, and so everyone was already ready to deplane and had their carryon bags, ready to leave. But we had to sit down and move to the proper gate. This process took over 30 minutes. Again, not Delta's fault - more so on the staff at JFK

It’s was good. There’s so much room for improvement though. Since the plane was small, there was no entertainment but for years now, the most jarring aspect of travel is the lack of tasty snacks.

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Everything you need to know for your flight from Key West to Chicago

Information on your arrival and departure airports

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