CHI - EYW

$98 Find Cheap Flights from Chicago 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 Chicago to Key West departing on 4/12. 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
1 adult, Economy, 0 bags

KAYAK searches 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
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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$309
Typical prices: $510-$333
American Airlines
Tue 5/12Sat 5/16
ORD - EYW • Non-stop
Cheapest one-way
$98
Typical prices: $191-$324
Multiple Airlines
Sun 4/12
ORD - EYW • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers extra legroom for comfort.
EYW is a ten-minute drive to Old Town Key West.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $309 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 3h 25m
Direct flights
Direct flights
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Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
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Top layover airports
Cheapest • Avg $313 (round-trip)
Shortest trip • 4h 57m (one-way)
Insights
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Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 5% compared to booking last minute.
Insights
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When to travel
Cheapest • 12% price drop
Most popular
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Flight Deals
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Flight Deals

Cheap Flights from Chicago to Key West (CHI-EYW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Key West

Tue, May 12 - Sat, May 16
American Airlines Logo
1:53 pm - 6:19 pm
ORD
-
EYW
3h 26mnonstop
American Airlines Logo
1:08 pm - 3:55 pm
EYW
-
ORD
3h 47mnonstop
$309American Airlines
Thu, Apr 30 - Sun, May 3
Multiple Airlines Logo
8:21 am - 12:26 pm
MDW
-
EYW
27h 05m
1 stop
Multiple Airlines Logo
2:09 pm - 7:46 am
EYW
-
MDW
18h 37m
1 stop
$310Multiple Airlines
Thu, Apr 9 - Sun, Apr 12
Multiple Airlines Logo
5:25 am - 3:42 pm
ORD
-
EYW
9h 17m
1 stop
Multiple Airlines Logo
12:25 pm - 11:17 am
EYW
-
ORD
23h 52m
1 stop
$313Multiple Airlines
Fri, Apr 10 - Sun, Apr 12
Multiple Airlines Logo
4:55 pm - 11:04 am
ORD
-
EYW
17h 09m
1 stop
Multiple Airlines Logo
4:22 pm - 12:24 pm
EYW
-
ORD
21h 02m
1 stop
$314Multiple Airlines
Thu, Apr 23 - Tue, Apr 28
Multiple Airlines Logo
1:27 pm - 1:35 pm
ORD
-
EYW
23h 08m
1 stop
Multiple Airlines Logo
1:01 pm - 6:20 pm
EYW
-
ORD
6h 19m
1 stop
$316Multiple Airlines
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
4:28 pm - 1:35 pm
ORD
-
EYW
20h 07m
2 stops
Multiple Airlines Logo
1:06 pm - 1:00 pm
EYW
-
ORD
24h 54m
1 stop
$317Multiple Airlines
Mon, May 11 - Mon, May 18
American Airlines Logo
5:00 am - 1:49 pm
ORD
-
EYW
7h 49m
1 stop
American Airlines Logo
6:46 pm - 9:35 pm
EYW
-
ORD
3h 49mnonstop
$318American Airlines
Thu, Apr 23 - Wed, Apr 29
Delta Logo
12:52 pm - 7:40 pm
MDW
-
EYW
5h 48m
1 stop
Delta Logo
6:23 pm - 10:28 pm
EYW
-
MDW
5h 05m
1 stop
$329Delta
Thu, Jul 2 - Sun, Jul 5
Allegiant Air Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
Allegiant Air Logo
8:48 pm - 2:38 pm
EYW
-
MDW
18h 50m
2 stops
$336Allegiant Air
Wed, Apr 29 - Sat, May 2
Delta Logo
10:41 am - 5:23 pm
MDW
-
EYW
5h 42m
1 stop
Delta Logo
6:18 pm - 10:28 pm
EYW
-
MDW
5h 10m
1 stop
$354Delta
Booking Insights

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

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

How much is a round-trip flight from Chicago to Key West?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Key West departing in May.

What is the cheapest Chicago to Key West flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Key West costs $249 on the route between Chicago O'Hare Intl Airport (ORD) and Key West (EYW). It is also the most popular route.

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

The average price of all round-trip flights from Chicago to Key West clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Key West, look for departures on Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Key West, Wednesday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Chicago to Key West?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago 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 to Key West is January, where tickets cost $385 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $521 and $489 respectively.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $442 on average.

How far in advance should I book a flight from Chicago to Key West?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Key West, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Key West, you should book around 3 weeks before departure, which saves you about 5% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Key West

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

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.

Paul Rubio

Paul Rubio

Expert on EYW

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

Good to know

Low seasonSeptember
Cheapest flight$98
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Chicago O'Hare Airport to Key West

When to book flights from Chicago to Key West

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

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

    In the last 3 days, the lowest price for a flight from Chicago to Key West was $98 for a one-way ticket and $309 for a round-trip.

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

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

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

    Chicago is served by 2 major airports and there is only 1 main airport in Key West. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Key West.

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

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

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

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

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

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

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

    There are nonstop flights from Chicago to Key West on a daily basis.

  • 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 $366 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $437 and an overall rating of 7.4.

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

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago 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 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 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 with another airline.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $168 or less one-way and $361 or less round-trip.

Prefer to fly direct from Chicago to Key West?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Key West.
Find which airlines fly direct from Chicago to Key West Airport, which days they fly and book direct flights.

Direct departures

Chicago to Key West

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

Key West to Chicago

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Reviews of the top 4 airlines serving from Chicago 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 Chicago 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.
7.9
DeltaOverall score based on 8357 reviews
7.2Food
7.8Entertainment
8.5Crew
7.9Comfort
8.1Boarding
Airline reviews

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

8.0 ExcellentMark, Mar 2026
SEA - MIA
Read more Delta reviews

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The whole experience was excellent. As it most often is with Delta

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

We had to take a bus to the plane with a old woman and carry on bags, and at landing at the airport we have to wait one hour seating on the plane waiting for a gate. We came back from Australia Bussines class Quantas 16 hours traveling, then wait in Dallas 7 hours for connection...honestly waiting 1 hour more at the plane was the worst part.

Flight delayed twice (not Spirit fault) No food served* No entertainment * *in response to my choices in the rating. None was provided so couldn’t rate properly

Pricing, boarding time communication, over priced baggage and overall service is lacking, seating unconfortable

Flight attendant was all so sweet and pilot got us to our destination safely and on time

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

The airplane rattled near the left wing as if several screws were loose. Then after we landed in Fort Lauderdale, we had to sit and wait on the runway for quite some time. It was very scary and TOTALLY unacceptable!

I was in the airport when I'll check the status of my flight and it was canceled and without any reason. The worst of the worst ...

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

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

Information on your arrival and departure airports