CHI - EYW

$87 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 4/25. 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
$296
Overall average: $549
Spirit Airlines
Mon 3/16Fri 3/20
ORD - EYW • 1 stop
Cheapest non-stop
$309
Typical prices: $427-$759
United Airlines
Thu 3/12Mon 3/16
ORD - EYW • Non-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
Delta
Cheapest • from $299 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines and United Airlines. Average duration is 3h 26m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
ORD
-
EYW
Cheapest
ORD
-
EYW
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Miami (MIA)
Cheapest • Avg $313 (round-trip)
Miami (MIA)
Shortest trip • 4h 57m (one-way)
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 7% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 12% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Key West!
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

Mon, Mar 16 - Fri, Mar 20
Multiple Airlines Logo
4:36 pm - 11:30 am
ORD
-
EYW
17h 54m
1 stop
Multiple Airlines Logo
1:06 pm - 11:38 pm
EYW
-
ORD
11h 32m
1 stop
$296Multiple Airlines
Mon, Mar 16 - Fri, Mar 20
Multiple Airlines Logo
6:10 pm - 11:30 am
ORD
-
EYW
16h 20m
1 stop
Multiple Airlines Logo
1:06 pm - 11:38 pm
EYW
-
ORD
11h 32m
1 stop
$297Multiple Airlines
Sat, Mar 14 - Thu, Mar 19
Multiple Airlines Logo
2:56 pm - 9:06 am
MDW
-
EYW
17h 10m
1 stop
Multiple Airlines Logo
9:46 am - 5:44 pm
EYW
-
MDW
8h 58m
1 stop
$298Multiple Airlines
Fri, Apr 24 - Mon, May 4
Multiple Airlines Logo
5:09 pm - 9:06 am
ORD
-
EYW
38h 57m
2 stops
Multiple Airlines Logo
12:06 pm - 11:22 am
EYW
-
ORD
24h 16m
1 stop
$298Multiple Airlines
Thu, Mar 19 - Tue, Mar 24
United Airlines Logo
5:55 pm - 10:19 pm
ORD
-
EYW
3h 24mnonstop
United Airlines Logo
6:28 pm - 11:44 pm
EYW
-
ORD
6h 16m
1 stop
$300United Airlines
Tue, Mar 17 - Thu, Mar 19
Multiple Airlines Logo
6:36 pm - 11:11 am
ORD
-
EYW
15h 35m
2 stops
Multiple Airlines Logo
12:25 pm - 7:51 pm
EYW
-
ORD
8h 26m
1 stop
$301Multiple Airlines
Wed, Mar 11 - Sun, Mar 15
Multiple Airlines Logo
4:43 pm - 9:06 am
ORD
-
EYW
15h 23m
2 stops
Multiple Airlines Logo
4:22 pm - 3:35 pm
EYW
-
ORD
24h 13m
1 stop
$302Multiple Airlines
Mon, Mar 16 - Thu, Mar 19
Spirit Airlines Logo
8:58 pm - 11:30 am
ORD
-
EYW
13h 32m
2 stops
Spirit Airlines Logo
12:25 pm - 7:51 pm
EYW
-
ORD
8h 26m
1 stop
$303Spirit Airlines
Tue, Mar 24 - Thu, Mar 26
Multiple Airlines Logo
4:33 pm - 11:11 am
MDW
-
EYW
17h 38m
1 stop
Multiple Airlines Logo
12:25 pm - 10:19 pm
EYW
-
MDW
10h 54m
2 stops
$304Multiple Airlines
Mon, Apr 27 - Wed, May 6
Delta Logo
6:00 am - 1:44 pm
MDW
-
EYW
6h 44m
1 stop
Delta Logo
6:23 pm - 10:28 pm
EYW
-
MDW
5h 05m
1 stop
$314Delta
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 March.

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 $494 and $468 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 2 weeks before departure, which saves you about 7% 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$87
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 13% 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

  • Does Key West Airport (EYW) have pet relief areas?

    Key West Airport has pet relief areas located at arrivals and departures. The designated relief areas in arrivals are outside the baggage claim, near the blue curbside for passenger pick-ups while those in departures are near the restrooms. You’ll find waste bags and trash containers which visitors can use to clean after their pets.

  • Where can I get a rental car at Key West Airport?

    Renting a car is sometimes more convenient than taking a taxi. Some rental car companies at Key Stone Airport are Hertz, Avis, Budget, and Dollar. Once you land at the airport and are looking to rent a car, head to the car rental counters in the arrivals baggage claim area.

  • Does Chicago Midway have a USO Military Lounge?

    USO military lounges provide a space for military personnel and their family members to sit, relax and wait for their flight. Chicago Midway Airport has a USO military lounge located at concourse C post-security. The lounge features free internet, complimentary food and beverages, reading materials, and a TV for entertainment.

  • Does Chicago O'Hare airport have social services agency?

    Chicago O'Hare has unique services for passengers who need guidance, support, and advocacy. Travelers Aid Chicago social service in terminal 2 of O'Hare Airport provides social assistance for travelers and visitors and crisis intervention information.

  • 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 $87 for a one-way ticket and $296 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 $404 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 $451 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 $158 or less one-way and $328 or less round-trip.
  • You might be flying from Chicago to Key West through Chicago Midway Airport (MDW). If this is the case and you have some time to kill at the airport, you can browse through the airport's art. Chicago Midway has art displays located at Concourse A.
  • Airports can get busy, causing passengers to feel overwhelmed. One of the unique things about Chicago Midway Airport is the yoga room. The room in concourse C provides a quiet and calming space for passengers to meditate and take a timeout while waiting for their flight.
  • You may be flying to Key West from Chicago O'Hare airport (ORD). If you're traveling with your family, you should wait for your flight at the family lounge. The lounge is in Terminal 2, just beyond security. It has a play area for kids, device charging stations, stroller parking spaces for those traveling with infants, and live entertainment at various times throughout the year, featuring musicians, caricature artists, and more.
  • Chicago O'Hare Airport is unique for a health club facility. If you're looking for a place to exercise before a flight, consider becoming a member of the Hilton athletic club. Members enjoy access to facilities like a sauna, steam room, lap pool, and locker rooms for a small fee. The health club is inside the Hilton Chicago O'Hare Airport Hotel, directly across the domestic terminals 1, 2, and 3.
  • Getting to the center or downtown Key West from the airport is easier with the availability of buses. The Keys West Transit and the Lower Keys shuttle serve the airport, with buses available every 30min. The bus service is at Faraldo Circle outside the Airport exit.

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 8237 reviews
7.8Entertainment
8.1Boarding
8.5Crew
7.2Food
7.9Comfort
Airline reviews

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

2.0 MediocreJason, Feb 2026
ATL - MCO
Read more Delta reviews

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

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

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.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

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?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

I needed a cheaper option than Southwest who are almost as bad as Spirit...did the check in the morning of the flight and assigned the last row, middle seat. Paid 20.00 at the airport for an exit row window in 19 and all 8 rows behind me which sold occupied on their seat map were empty....so they force to you to pay for a better seat....I was alone in row 19 and shortly after take off two huge fat people came and grabbed the other seats, I rang the call button for the attendant and said I paid 20.00 for this seat and they just moved in here...I either want to be reseated, or have them take their original seats or a refund of what I paid, the attendant made them move back to their original seats. Worst, worst worst airline in the air....never again, never again, never again.

It was cancelled a few hours before take off. Spirit has yet to confirm I will be refunded for the trip

gate agents with the different rules at the different airports. made me pay for my bag as a carry on instead of a personal item, yet it fit under the seat on the way from Indy to Ft Laud

charging $3 for really bad and cold coffee on airplane flight is ridiculous.

Checking in and getting to gate fast and leasy at Laguardia airport. There is no entertainment on the plane and food was for purchase. Great experience flying with spirit

Flight was delayed for 12 h. They should stop overlooking flights.

Got surprised by passing an additional fee when selecting seats. No snack or drink offered. Will never use spirit again.

Went as planned. No wifi included and no screens. No free snacks. Didn't buy food so can't rate that. Unable to charge devices on plane. Staff were friendly and flight was fast, cheap and convenient.

Kayak and Spirit could not meaningfully share itinerary data, leading to many hours of remediation.

Do not fly with Spirit. They will leave you canceled if their flight is not 110% booked.

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

Information on your arrival and departure airports