Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

CHI - EYW

Find cheap flights from Chicago to Key West from $109

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 7/17. 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
Mon 6/3
Mon 6/10

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 43,693,958 times on KAYAK, and here is why:

Save 22% 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
10:11 am - 5:09 pmMDW-EYW
5h 58m1 stop
6:05 pm - 9:44 pmEYW-MDW
4h 39m1 stop
$216Delta
Find Deal
Wed, Sep 4 - Tue, Sep 10
10:11 am - 5:09 pmMDW-EYW
5h 58m1 stop
6:05 pm - 9:44 pmEYW-MDW
4h 39m1 stop
$233Delta
Find Deal
Wed, Sep 4 - Tue, Sep 10
1:05 pm - 7:33 pmMDW-EYW
5h 28m1 stop
6:05 pm - 9:44 pmEYW-MDW
4h 39m1 stop
$248Delta
Find Deal
Wed, Sep 11 - Tue, Sep 17
12:22 pm - 7:40 pmORD-EYW
6h 18m1 stop
12:39 pm - 4:49 pmEYW-ORD
5h 10m1 stop
$248Delta
Find Deal
Fri, Jun 14 - Mon, Jun 17
8:30 am - 4:08 pmORD-EYW
6h 38m1 stop
12:46 pm - 5:45 pmEYW-ORD
5h 59m1 stop
$255American Airlines
Find Deal
Wed, May 29 - Wed, Jun 5
8:30 am - 4:08 pmORD-EYW
6h 38m1 stop
2:29 pm - 7:54 pmEYW-ORD
6h 25m1 stop
$256American Airlines
Find Deal
Sat, May 25 - Tue, May 28
8:04 pm - 9:02 amORD-EYW
11h 58m1 stop
5:09 pm - 4:28 pmEYW-ORD
24h 19m2 stops
Thu, Jun 6 - Sun, Jun 9
7:07 pm - 9:02 amORD-EYW
12h 55m1 stop
5:09 pm - 5:40 pmEYW-ORD
25h 31m2 stops
Sun, Jun 2 - Sun, Jun 9
10:43 am - 2:40 pmORD-EYW
26h 57m1 stop
12:30 pm - 11:30 pmEYW-ORD
12h 00m2 stops
$453United Airlines
Find Deal
Sat, May 11 - Tue, May 14
2:25 pm - 2:25 pmORD-EYW
23h 00m2 stops
11:30 am - 9:19 pmEYW-ORD
10h 49m2 stops
$493United Airlines
Find Deal
Wed, May 29 - Wed, Jun 5

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 $220 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 $317.

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 Monday, with Thursday 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 $308 on average. On the other hand, the most expensive months are March and February, where the average cost of tickets is $600 and $531 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 82 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 ($109) and Allegiant Air ($230), and the lowest round-trip tickets were found on Delta ($216) and American Airlines ($255).

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

March

Cheapest flight

$109
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 29% increase in price.
Flight from Chicago Midway 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 $109 for a one-way ticket and $216 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 American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Key West are Delta and American Airlines. With an average price for the route of $351 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $474 and an overall rating of 7.3.

  • 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 $249 or less one-way and $396 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 9137 reviews
7.3Entertainment
8.2Boarding
8.6Crew
7.9Comfort
7.3Food
Airline reviews

My baggage was in another flight, anit was delayed for one hour.

4.0 OkayAnonymous, May 2024SEA - LAX
Read more about Alaska Airlines reviews

My baggage was in another flight, anit was delayed for one hour.

The maintenance delay was seemingly handled very poorly... Little to no information was provided to the passengers sitting on board for an extended period of time. On a brighter note, at least the cabin crew (flight attendants) did the best they could. They seemingly were provided very little information with regards to the delay. Unless absolutely beyond my control, I can’t imagine buying a ticket on Alaska airlines again, based on this and a previous experience my wife recently had, along with complaints overheard from other passengers.

They oversold my flight by 9 seats so when I went to check in I was not assigned a seat and the only one available if I didn’t want to chance it were 100 dollars more

The seats were incredibly small and the attendants were grumpy the whole time.

Honestly, there was not much they could do. Due to wind, the flight was delayed for several hours because we had to be diverted to San Jose where we needed to refuel before departing to Hawaii. Wish they had offered some snacks during the delays/diversion because we had to wait such a long time to finally get our food served during the flight after leaving California.

The only issue was in the wheelchair waiting area before we got on the plane. They seemed very disorganized. Everyone we encountered after that was great! We loved Cassandra at check-in. She was awesome. The flight attendants were wonderful too! The lady helping with the waiting wheelchair when we got off the plane was awesome too!

They canceled the flight 30 minutes prior to departure without any heads up.

Like South West(2 check in baggage free) if Alaskan Airlines could give at least one check in baggage free then it would be great.

Expect to get miles for us having to miss our first planned flight due to them waiting on passengers that decided to be late to the airport.

Was not happy that we had to wait an additional 50 minutes for passengers that were still in TSA. This delay made us miss our connecting flight in Seattle to get home to tuck in our two little toddlers. We ran off the plane and ran across the entire airport trying to make this flight only to get to the gate to see that they have ended boarding. So they were willing to wait for passengers in Hawaii but not Seattle?? Especially when this wasn't even our fault. I expect to receive miles for missing our flight and spending an additional 4 hours in Seattle.

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.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

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.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

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.
7/17Wed
1 stopDelta
5h 35mMDW-EYW
$109
7/17Wed
1 stopDelta
6h 49mORD-EYW
$109
7/17Wed
2 stops
20h 16mORD-EYW
$181
7/17Wed
3 stops
23h 30mORD-EYW
$216
8/30Fri
2 stopsAllegiant Air
17h 22mMDW-EYW
$230
8/12Mon
1 stopDelta
5h 58mMDW-EYW
$254
6/6Thu
1 stopDelta
5h 00mORD-EYW
$254
6/7Fri
2 stopsAmerican Airlines
7h 59mORD-EYW
$264
8/30Fri
1 stopDelta
5h 58mMDW-EYW
$289
6/6Thu
2 stopsAmerican Airlines
7h 59mORD-EYW
$298

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.
5/9Thu
multi-stopDelta
6h 20mORD-EYW
5/12Sun
multi-stopDelta
5h 14mEYW-ORD
$428
5/9Thu
multi-stopAmerican Airlines
6h 48mORD-EYW
5/12Sun
multi-stopAmerican Airlines
5h 04mEYW-ORD
$490
5/6Mon
multi-stopUnited Airlines
9h 24mORD-EYW
5/10Fri
multi-stopUnited Airlines
22h 44mEYW-ORD
$538
5/6Mon
multi-stopUnited Airlines
9h 24mORD-EYW
5/10Fri
multi-stopUnited Airlines
27h 15mEYW-ORD
$543
5/9Thu
multi-stopAmerican Airlines
10h 31mORD-EYW
5/12Sun
multi-stopAmerican Airlines
11h 14mEYW-ORD
$736
5/5Sun
multi-stopUnited Airlines
26h 42mORD-EYW
5/7Tue
multi-stopUnited Airlines
28h 23mEYW-ORD
$862
5/6Mon
multi-stopUnited Airlines
14h 22mORD-EYW
5/10Fri
multi-stopUnited Airlines
12h 45mEYW-ORD
$905
5/5Sun
multi-stopUnited Airlines
26h 42mORD-EYW
5/7Tue
multi-stopUnited Airlines
11h 22mEYW-ORD
$917
5/6Mon
multi-stopDelta
6h 15mMDW-EYW
5/10Fri
multi-stopDelta
7h 15mEYW-MDW
$933
5/5Sun
nonstopAmerican Airlines
3h 14mORD-EYW
5/7Tue
multi-stopAmerican Airlines
7h 50mEYW-ORD
$1,027

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
$317