CHI - EYW

$126 Find Cheap Flights from Chicago to Key West - Compare and Save

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 8/22. 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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Everything you should know

Cheapest round-trip
$282
Allegiant Air
Thu 8/13Thu 8/20
MDW - EYW • 1 stop
Cheapest non-stop
$309
Typical prices: $287-$344
American Airlines
Sun 8/30Sun 9/6
ORD - EYW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Main Cabin Extra adds early boarding and drinks; Wi-Fi is free for 20 minutes.
United Economy Plus adds up to 6 inches of legroom; Priority Boarding helps bin space.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $309 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 3h 22m
Direct flights
Direct flights
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+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $404 (round-trip)
Shortest trip • 5h 07m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 15% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 49% price drop
Most popular
Good to know
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+1
+1
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Flight Deals
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Expert advice
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

Thu, Aug 13 - Thu, Aug 20
Multiple Airlines Logo
2:49 pm - 9:41 am
MDW
-
EYW
17h 52m
1 stop
Multiple Airlines Logo
11:04 am - 10:47 pm
EYW
-
MDW
12h 43m
2 stops
$282Multiple Airlines
Wed, Aug 19 - Sun, Aug 23
Multiple Airlines Logo
7:44 pm - 9:10 am
ORD
-
EYW
12h 26m
1 stop
Multiple Airlines Logo
12:05 pm - 1:20 pm
EYW
-
ORD
26h 15m
1 stop
$286Multiple Airlines
Thu, Aug 13 - Thu, Aug 20
Multiple Airlines Logo
5:13 pm - 11:27 am
ORD
-
EYW
17h 14m
1 stop
Multiple Airlines Logo
12:05 pm - 11:08 pm
EYW
-
ORD
12h 03m
1 stop
$291Multiple Airlines
Thu, Oct 1 - Thu, Oct 8
Multiple Airlines Logo
9:26 am - 10:19 am
ORD
-
EYW
23h 53m
1 stop
Multiple Airlines Logo
10:59 am - 11:55 pm
EYW
-
ORD
13h 56m
1 stop
$295Multiple Airlines
Sun, Aug 30 - Sun, Sep 6
American Airlines Logo
12:08 pm - 4:27 pm
ORD
-
EYW
3h 19mnonstop
American Airlines Logo
4:58 pm - 7:50 pm
EYW
-
ORD
3h 52mnonstop
$309American Airlines
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
11:59 am - 4:18 pm
ORD
-
EYW
3h 19mnonstop
American Airlines Logo
8:09 pm - 12:35 am
EYW
-
ORD
5h 26m
1 stop
$319American Airlines
Fri, Aug 14 - Tue, Aug 18
Delta Logo
12:46 pm - 7:57 pm
MDW
-
EYW
6h 11m
1 stop
Delta Logo
6:15 pm - 10:36 pm
EYW
-
MDW
5h 21m
1 stop
$329Delta
Thu, Aug 13 - Thu, Aug 20
Delta Logo
12:46 pm - 7:57 pm
MDW
-
EYW
6h 11m
1 stop
Delta Logo
6:15 pm - 10:36 pm
EYW
-
MDW
5h 21m
1 stop
$354Delta
Tue, Jul 28 - Tue, Aug 4
Delta Logo
11:05 am - 7:51 pm
MDW
-
EYW
7h 46m
1 stop
Delta Logo
6:15 pm - 10:36 pm
EYW
-
MDW
5h 21m
1 stop
$356Delta
Fri, Aug 7 - Mon, Aug 10
Delta Logo
10:54 am - 5:20 pm
MDW
-
EYW
5h 26m
1 stop
Delta Logo
7:40 am - 11:51 am
EYW
-
MDW
5h 11m
1 stop
$359Delta
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 August.

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 $319 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 Thursday, as it's usually the priciest day. When flying back from Key West, Wednesday is the cheapest day to fly and Monday 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 February, where tickets cost $104 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $249 and $249 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.

No, with an average price for the route of $413, prices are generally cheapest when you fly direct.

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 15% 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$126
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly with an average 20% 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 5 days, the lowest price for a flight from Chicago to Key West was $126 for a one-way ticket and $282 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 $358 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $432 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 $233 or less one-way and $382 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 3 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.
7.8
DeltaOverall score based on 8451 reviews
8.5Crew
8.1Boarding
7.8Comfort
7.8Entertainment
7.2Food
Airline reviews

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

2.0 MediocreJean, Jun 2026
MDW - ATL
Read more Delta reviews

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

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

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?

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

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

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Always wish for more healthy, gluten free options. We have to bring our own.

Our seats were all the way in back of the plane,

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

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

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

The Airline was not prepared for weather delays. We were held up due to an incoming flight being delayed and so we did not have a flight crew. This caused an extra delay for departure by 2 hours.

We sat on the plane for 1 hour because the airline was short handed could not be unloading.

From the moment I walked into the airport in Chicago to the moment I was walking off the plane in Florida I had an unforgettable experience! I was traveling with my 3 month old by myself and everyone just made sure I was taken care of. I couldn’t thank them enough!

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

Information on your arrival and departure airports