Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

CHI - EYW

$108 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 7/2. 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.
1 adult
0 bags
Thu 6/27
Thu 7/4

Search 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
In the last 7 days travelers have searched 42,816,550 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
10:40 am - 2:50 pmORD-EYW
3h 10mnonstop
4:00 pm - 6:24 pmEYW-ORD
3h 24mnonstop
$229United Airlines
Find Deal
Sun, Nov 17 - Sat, Nov 23
6:00 am - 11:47 amORD-EYW
4h 47m1 stop
7:00 am - 2:12 pmEYW-ORD
8h 12m1 stop
$232Delta
Find Deal
Wed, Sep 4 - Tue, Sep 10
4:32 pm - 9:09 amORD-EYW
15h 37m2 stops
5:30 pm - 8:34 amEYW-ORD
16h 04m1 stop
Wed, Jun 26 - Wed, Jul 3
6:16 pm - 9:09 amORD-EYW
13h 53m1 stop
5:30 pm - 8:34 amEYW-ORD
16h 04m1 stop
Wed, Jun 26 - Wed, Jul 3
12:22 pm - 7:38 pmORD-EYW
6h 16m1 stop
6:03 pm - 11:54 pmEYW-ORD
6h 51m1 stop
$248Delta
Find Deal
Wed, Aug 14 - Mon, Aug 19
10:40 am - 2:50 pmORD-EYW
3h 10mnonstop
5:25 pm - 11:42 pmEYW-ORD
7h 17m1 stop
$258United Airlines
Find Deal
Wed, Nov 20 - Wed, Mar 19
7:00 am - 4:14 pmORD-EYW
32h 14m3 stops
5:30 pm - 8:34 amEYW-ORD
16h 04m1 stop
Wed, Jun 26 - Wed, Jul 3
9:22 am - 5:08 pmORD-EYW
6h 46m1 stop
12:42 pm - 6:47 pmEYW-ORD
7h 05m1 stop
$268Delta
Find Deal
Tue, Aug 6 - Mon, Aug 12
8:40 am - 4:43 pmORD-EYW
7h 03m1 stop
2:56 pm - 9:33 pmEYW-ORD
7h 37m1 stop
$272American Airlines
Find Deal
Fri, Sep 6 - Sun, Sep 8
6:02 am - 4:24 pmORD-EYW
9h 22m1 stop
2:30 pm - 8:02 pmEYW-ORD
6h 32m1 stop
$273American Airlines
Find Deal
Thu, Jun 27 - Thu, Jul 4

Flights from Chicago to Key West - Travel Insights & Trends

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.

What is the cheapest Chicago to Key West flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Key West.
Our data shows that the cheapest route for a one-way flight from Chicago to Key West cost $262 and was between Chicago O'Hare Intl Airport and Key West. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $325.

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

The average price of all flights from Chicago to Key West clicked on KAYAK for each day over the last 12 months.
For Chicago to Key West, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Key West back to Chicago, the best deals are generally found on Sunday, with Saturday being 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 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 August, where tickets cost $310 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $529 and $518 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Chicago to Key West, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 60 days before departure.

Which airlines provide the cheapest flights from Chicago to Key West?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Key West from Chicago were found on Delta ($108) and American Airlines ($139), and the lowest round-trip tickets were found on United Airlines ($229) and Delta ($232).

Which cabin class options are there for flights between Chicago and Key West?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are First, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Good to know

Low season

September

High season

December

Cheapest flight

$108
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 14% 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 $108 for a one-way ticket and $229 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?

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

  • What is the most popular layover when flying to Key West from Chicago?

    Charlotte is the most popular layover city among KAYAK users traveling from Chicago to Key West.

  • 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 $346 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 $479 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.

See more FAQs

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 $404 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.
See more tips

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.
8.0
Alaska AirlinesOverall score based on 9192 reviews
7.9Comfort
7.3Food
7.3Entertainment
8.2Boarding
8.6Crew
Airline reviews

The boarding gate is literally just an aisle to the concourse. There is no seating and it's shared with several other airlines. It's crowded, hot, and standing-room only. It's difficult to hear gate announcements over the PA system with too many other carriers crammed into a small space. I've enjoyed flying AA in the past on the west coast, but the BNA single gate experience is horrendous! Never again from BNA to SEA with AA.

4.0 OkayBrent, May 2024SEA - BNA
Read more about Alaska Airlines reviews

The boarding gate is literally just an aisle to the concourse. There is no seating and it's shared with several other airlines. It's crowded, hot, and standing-room only. It's difficult to hear gate announcements over the PA system with too many other carriers crammed into a small space. I've enjoyed flying AA in the past on the west coast, but the BNA single gate experience is horrendous! Never again from BNA to SEA with AA.

I would have liked it to have been easier to order food for the flight. My son was not happy with the snack pack I bought him and it was a very long flight for a little boy to go without food.

It was a partial full flight. But even with a spare seat it was hard to get comfortable More on me being a wide body probably

I had a middle seat in between two large men. It was a redeye so needless to say I didn’t get a minute of sleep. One guy was pouring over into my seat the other kept falling onto my shoulder

Our flights using Alaska Airlines went great! All of the flight attendants were very friendly. Big shout out to the pilots for getting us to and from our destinations safely!

I can’t complain. Perhaps passing out headphones, but it was on me to bring my own since I could have used some for my personal device.

Easy and quick boarding. A bit of a hard landing at PDX

Great price on internet. I love that WiFi was so affordable. Got a lot done.

Very close to on-time takeoff and landing. Attendants were all great - Julia was best! Joined the Alaska Air Rewards and will fly with them again!

I didn't have food or use entertainment, so those evaluations are invalid.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

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.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

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.

The control panel for the seat back screen did not work at all after takeoff.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

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

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Book cheap flights from Chicago to Key West

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Key West found on KAYAK in the last 72 hours.
7/2Tue
1 stopDelta
6h 08mORD-EYW
$108
7/1Mon
1 stopAmerican Airlines
9h 22mORD-EYW
$139
7/2Tue
2 stopsDelta
14h 23mORD-EYW
$158
7/3Wed
1 stopDelta
6h 50mORD-EYW
$159
7/1Mon
2 stopsDelta
18h 30mORD-EYW
$179
6/29Sat
2 stops
20h 34mORD-EYW
$206
7/6Sat
1 stopUnited Airlines
10h 25mORD-EYW
$207
8/28Wed
2 stopsUnited Airlines
24h 26mORD-EYW
$212
9/16Mon
1 stopUnited Airlines
26h 30mORD-EYW
$235
7/2Tue
2 stopsAmerican Airlines
7h 59mORD-EYW
$264

Search by stops

Search by airline

Search by price

Last minute flights from Chicago to Key West

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Key West that are departing in the next 10 days.
5/30Thu
multi-stopDelta
5h 00mORD-EYW
6/4Tue
multi-stopDelta
6h 40mEYW-ORD
$428
5/30Thu
multi-stopAmerican Airlines
5h 13mORD-EYW
6/3Mon
multi-stopAmerican Airlines
6h 49mEYW-ORD
$435
5/30Thu
multi-stopAmerican Airlines
6h 48mORD-EYW
6/4Tue
multi-stopAmerican Airlines
8h 18mEYW-ORD
$440
5/30Thu
multi-stopAmerican Airlines
10h 31mORD-EYW
6/4Tue
multi-stopAmerican Airlines
9h 00mEYW-ORD
$525
5/31Fri
multi-stopUnited Airlines
7h 09mORD-EYW
6/4Tue
multi-stopUnited Airlines
8h 15mEYW-ORD
$563
6/2Sun
multi-stopUnited Airlines
27h 00mORD-EYW
6/4Tue
multi-stopUnited Airlines
22h 51mEYW-ORD
$636
6/2Sun
multi-stopUnited Airlines
23h 37mORD-EYW
6/4Tue
multi-stopUnited Airlines
22h 51mEYW-ORD
$641
5/31Fri
multi-stopUnited Airlines
15h 54mORD-EYW
6/4Tue
multi-stopUnited Airlines
12h 45mEYW-ORD
$725
6/2Sun
multi-stopDelta
5h 58mMDW-EYW
6/4Tue
multi-stopDelta
4h 51mEYW-MDW
$933
6/2Sun
multi-stopDelta
5h 58mMDW-EYW
6/4Tue
multi-stopDelta
12h 02mEYW-MDW
$1,253

Search by stops

Search by airline

Search by price

Flights to Key West

Destination:

Key West (EYW)United States

Return flight deals:

Key West - Chicago

Cabin classes:

$1,058
$1,053
$754
$325