EYW - CHI

$162 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 9/2. 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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KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
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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Flights Deals

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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Key West to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
6:25 pm - 11:58 pmEYW-ORD
6h 33m1 stop
Delta Logo
11:20 am - 7:39 pmORD-EYW
7h 19m1 stop
$314Delta
Find Deal
Mon, Jun 2 - Tue, Jun 17
Delta Logo
6:25 pm - 11:58 pmEYW-ORD
6h 33m1 stop
Delta Logo
1:30 pm - 8:07 pmORD-EYW
5h 37m1 stop
$326Delta
Find Deal
Thu, May 29 - Thu, Jun 5
American Airlines Logo
12:49 pm - 3:28 pmEYW-ORD
3h 39mnonstop
American Airlines Logo
10:13 am - 7:02 pmORD-EYW
7h 49m1 stop
$375American Airlines
Find Deal
Thu, May 29 - Thu, Jun 5
Delta Logo
6:25 pm - 11:58 pmEYW-ORD
6h 33m1 stop
Delta Logo
11:23 am - 8:07 pmORD-EYW
7h 44m1 stop
$385Delta
Find Deal
Fri, May 23 - Sun, May 25
United Airlines Logo
6:45 pm - 9:24 amEYW-ORD
15h 39m1 stop
United Airlines Logo
2:24 pm - 6:05 pmORD-EYW
26h 41m2 stops
$400United Airlines
Find Deal
Mon, Jun 2 - Tue, Jun 17
United Airlines Logo
8:45 am - 9:39 amEYW-ORD
25h 54m1 stop
United Airlines Logo
8:52 am - 8:00 amORD-EYW
22h 08m2 stops
$416United Airlines
Find Deal
Fri, May 23 - Sun, May 25
United Airlines Logo
2:45 pm - 2:39 pmEYW-ORD
24h 54m1 stop
United Airlines Logo
5:55 pm - 8:00 amORD-EYW
13h 05m1 stop
$424United Airlines
Find Deal
Tue, Jun 24 - Fri, Jun 27
American Airlines Logo
5:30 pm - 10:48 pmEYW-ORD
6h 18m1 stop
American Airlines Logo
8:05 am - 12:19 pmORD-EYW
3h 14mnonstop
$437American Airlines
Find Deal
Fri, May 16 - Mon, May 19
American Airlines Logo
3:17 pm - 7:35 pmEYW-ORD
5h 18m1 stop
American Airlines Logo
9:22 am - 7:02 pmORD-EYW
8h 40m2 stops
$439American Airlines
Find Deal
Thu, May 29 - Thu, Jun 5
American Airlines Logo
5:30 pm - 10:48 pmEYW-ORD
6h 18m1 stop
American Airlines Logo
8:05 am - 2:37 pmORD-EYW
5h 32m1 stop
$447American Airlines
Find Deal
Fri, May 16 - Mon, May 19
Expert advice

Expert advice for your flight from Key West to Chicago

 
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.
KAYAK teamed up with top travel experts to share the best tips for your 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
Useful Info

KAYAK's insights & trends for Key West to Chicago flights

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 $294 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 $294.

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.

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 $715, prices are generally cheapest when you fly direct.

Good to know

Low seasonJune
High seasonDecember
Cheapest flight$162
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 0% 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 $162 for a one-way ticket and $314 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 is the only airline alliance operating flights between Key West and Chicago.

  • 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 $332 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 $442 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.

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 $269 or less one-way and $403 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

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

Direct returns

Chicago 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 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 7934 reviews
8.5Crew
8.2Boarding
7.9Entertainment
7.3Food
7.9Comfort
Airline reviews

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

10.0 ExcellentGary, Apr 2025TPA - LAX
Read more Delta reviews

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

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.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

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

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

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.

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

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