EYW - CHI

$109 Find Cheap Flights from Key West to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Chicago departing on 12/18. 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

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Chicago, 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 Key West to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 47,107,125 times on KAYAK, and here is why:

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Cheap Flight Deals from Key West to Chicago (EYW-CHI)

 
These are the cheapest deals for flights from Key West to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Key West to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Key West to Chicago.

Recent one-way flight deals from Key West to Chicago

Only flying one-way? Below are some of the best one-way flight deals from Key West to Chicago found on KAYAK recently.

Recent last minute flight deals from Key West to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Key West to Chicago.

Recent direct flight deals from Key West to Chicago

The latest deals for direct flights from Key West to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Key West to Chicago

Find recent round-trip train or bus tickets from Key West to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
4:12 pm - 6:41 pmEYW-ORD
3h 29mnonstop
7:10 am - 11:30 amORD-EYW
3h 20mnonstop
$249United Airlines
Find Deal
Sun, Dec 22 - Mon, Dec 30
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
10:28 am - 7:07 pmORD-EYW
7h 39m1 stop
$254American Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 11
4:50 pm - 12:30 amEYW-ORD
8h 40m1 stop
7:10 am - 11:30 amORD-EYW
3h 20mnonstop
$259United Airlines
Find Deal
Sun, Dec 22 - Mon, Dec 30
7:00 am - 1:43 pmEYW-ORD
7h 43m1 stop
5:45 am - 11:38 amORD-EYW
4h 53m1 stop
$268Delta
Find Deal
Thu, Jan 30 - Sun, Feb 2
4:00 pm - 9:53 pmEYW-ORD
6h 53m1 stop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$279American Airlines
Find Deal
Thu, Jan 30 - Sun, Feb 2
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$289American Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 11
2:55 pm - 7:30 pmEYW-ORD
5h 35m1 stop
8:05 am - 3:30 pmORD-EYW
6h 25m1 stop
$308American Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 11
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
6:00 am - 3:27 pmORD-EYW
8h 27m1 stop
$324American Airlines
Find Deal
Sun, Dec 22 - Mon, Dec 30
12:26 pm - 2:55 pmEYW-ORD
3h 29mnonstop
7:10 am - 11:30 amORD-EYW
3h 20mnonstop
$329United Airlines
Find Deal
Fri, Dec 27 - Fri, Jan 3
6:02 pm - 10:06 pmEYW-MDW
5h 04m1 stop
6:00 am - 12:07 pmMDW-EYW
5h 07m1 stop
$688Delta
Find Deal
Fri, Dec 27 - Fri, Jan 3
6:30 pm - 11:58 pmEYW-ORD
6h 28m1 stop
$109Delta
Find Deal
Wed, Dec 18
5:31 pm - 8:29 amEYW-RFD
15h 58m1 stop
$115Allegiant Air
Find Deal
Thu, Dec 5
9:03 am - 5:20 pmEYW-ORD
9h 17m1 stop
Sun, Jan 12
10:00 am - 3:16 pmEYW-MDW
6h 16m1 stop
Sun, Jan 12
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
$140United Airlines
Find Deal
Wed, Dec 18
1:01 pm - 3:29 pmEYW-ORD
3h 28mnonstop
$150American Airlines
Find Deal
Wed, Feb 19
8:53 am - 10:29 pmEYW-ORD
14h 36m1 stop
Sun, Feb 23
8:01 am - 12:12 pmEYW-ORD
5h 11m1 stop
$159American Airlines
Find Deal
Wed, Jan 1
7:25 am - 12:48 pmEYW-ORD
6h 23m1 stop
$169Delta
Find Deal
Tue, Dec 17
10:55 am - 6:49 pmEYW-ORD
8h 54m1 stop
$190United Airlines
Find Deal
Fri, Jan 17
12:55 pm - 3:26 pmEYW-ORD
3h 31mnonstop
8:09 am - 12:25 pmORD-EYW
3h 16mnonstop
$349American Airlines
Find Deal
Fri, Nov 22 - Mon, Nov 25
1:39 pm - 7:33 pmEYW-ORD
6h 54m1 stop
8:09 am - 12:25 pmORD-EYW
3h 16mnonstop
$359American Airlines
Find Deal
Fri, Nov 22 - Mon, Nov 25
6:13 pm - 11:59 pmEYW-ORD
6h 46m1 stop
7:10 am - 1:18 pmORD-EYW
5h 08m1 stop
$377Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
12:33 pm - 5:54 pmEYW-MDW
6h 21m1 stop
12:43 pm - 8:30 pmMDW-EYW
6h 47m1 stop
$377Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
12:55 pm - 3:26 pmEYW-ORD
3h 31mnonstop
12:15 pm - 6:48 pmORD-EYW
5h 33m1 stop
$409American Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
12:55 pm - 6:54 pmEYW-ORD
6h 59m1 stop
1:50 pm - 6:55 pmORD-EYW
28h 05m2 stops
$554United Airlines
Find Deal
Fri, Nov 22 - Mon, Nov 25
12:55 pm - 6:54 pmEYW-ORD
6h 59m1 stop
6:00 am - 6:55 pmORD-EYW
11h 55m2 stops
$593United Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
10:11 am - 9:20 amEYW-ORD
24h 09m2 stops
11:51 am - 4:25 pmORD-EYW
27h 34m3 stops
Fri, Nov 22 - Mon, Nov 25
12:55 pm - 3:26 pmEYW-ORD
3h 31mnonstop
8:09 am - 12:25 pmORD-EYW
3h 16mnonstop
$649American Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
3:05 pm - 11:59 pmEYW-ORD
9h 54m2 stops
9:15 am - 6:55 pmORD-EYW
8h 40m2 stops
$743United Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
4:12 pm - 6:41 pmEYW-ORD
3h 29mnonstop
7:10 am - 11:30 amORD-EYW
3h 20mnonstop
$249United Airlines
Find Deal
Sun, Dec 22 - Mon, Dec 30
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$289American Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 11
12:26 pm - 2:55 pmEYW-ORD
3h 29mnonstop
7:10 am - 11:30 amORD-EYW
3h 20mnonstop
$329United Airlines
Find Deal
Fri, Dec 27 - Fri, Jan 3
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$649United Airlines
Find Deal
Thu, Jan 9 - Fri, Jan 17
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
$835United Airlines
Find Deal
Sun, Dec 1 - Thu, Dec 5

Flights from Key West to Chicago - Travel Insights & Trends

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

What is the cheapest Key West to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Key West to Chicago.
Our data shows that the cheapest route for a one-way flight from Key West to Chicago cost $213 and was between Key West and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $134.

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

The average price of all flights from Key West to Chicago clicked on KAYAK for each day over the last 12 months.
For Key West to Chicago, Monday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Chicago back to Key West, the best deals are generally found on Tuesday, with Thursday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Key West to Chicago, 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 Key West to Chicago is August, where tickets cost $294 on average. On the other hand, the most expensive months are November and February, where the average cost of tickets is $530 and $461 respectively.

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

The average 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 1 stop layover the cheapest option at $766 on average

Good to know

Low season

May

High season

February

Cheapest flight

$109
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 13% increase in price.
Flight from Key West to Chicago O'Hare Airport

When to book flights from Key West to Chicago

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

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

    In the last 3 days, the lowest price for a flight from Key West to Chicago was $109 for a one-way ticket and $249 for a round-trip.

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

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

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

    When flying out of Key West you will be using Key West. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

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

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

    The Boeing 737-700 is the aircraft model that flies most regularly on the Key West to Chicago flight route.

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

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

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

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

  • Which is the best airline for flights from Key West to Chicago, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Key West to Chicago are Delta and United Airlines. With an average price for the route of $388 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 $408 and an overall rating of 7.4.

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

    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 Key West to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Key West 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 Key West to Chicago?

    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 Chicago with an airline and back to Key West with another airline.

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

    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 Chicago from Key West up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Key West to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $253 or less one-way and $239 or less round-trip.

Prefer to fly non-stop from Key West to Chicago?

Find which airlines fly direct from Key West Airport to Chicago, which days they fly and book direct flights.

Nonstop departures

Key West to Chicago

Monday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Tuesday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Wednesday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Thursday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Friday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Saturday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Sunday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

See more direct flights

Nonstop returns

Chicago to Key West

Monday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Tuesday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Wednesday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Thursday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Friday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Saturday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Sunday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

See more direct flights
See more direct flights

Top 3 airlines serving from Key West to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Key West to Chicago. 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 Key West to Chicago? 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
DeltaOverall score based on 8765 reviews
8.5Crew
7.9Comfort
7.9Entertainment
7.3Food
8.2Boarding
Airline reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

8.0 ExcellentAndrew, Nov 2024MCO - LGA
Read more Delta reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Great - This was the last flight before hurricane closures and did a quick turnaround to get the plane heading north. Much appreciated.

I liked the screens in the seat headrest with movies to watch. I didn’t like being forced to check my carryon bag and being told there wasn’t room for my bag - when there were 5 bins sitting empty on takeoff. I didn’t like the “I don’t give a fig” attitude of the flight attendants and the delta gate attendants when I asked why they decided to put me out. They gave me a 1800 number to call but I can’t get a live person on the phone. Customer service is non existent. My business must not be that important to them.

It was not in Delta's control, but when we landed, we ended up parking at the wrong gate, and so everyone was already ready to deplane and had their carryon bags, ready to leave. But we had to sit down and move to the proper gate. This process took over 30 minutes. Again, not Delta's fault - more so on the staff at JFK

It’s was good. There’s so much room for improvement though. Since the plane was small, there was no entertainment but for years now, the most jarring aspect of travel is the lack of tasty snacks.

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

Love delta but the delays and long waits for updates was just too much this time.

Flight for canceled. Horrible experience.. had to rent a car to drive myself up here.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

Exceptional, I’d like to specifically recognize Robert for his outstanding customer service. He is professional, pleasant, and personable.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

This flight was fine but had no time to breathe as the connection was late from Sea to ORD.. Super stressful. If we checked bags, the trip would have been very distressed.

Seats were very uncomfortable. I paid extra for a seat with more leg room, the seat was no different than a seat at the back of the plane. Flight attendant was rude.

the food choice of packaged chips and popcorn was utterly ridiculous for first class

Book cheap flights from Key West to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Key West to Chicago found on KAYAK in the last 72 hours.
12/18Wed
1 stopDelta
6h 28mEYW-ORD
$109
12/5Thu
1 stopAllegiant Air
15h 58mEYW-RFD
$115
1/12Sun
1 stop
9h 17mEYW-ORD
$128
1/12Sun
1 stop
6h 16mEYW-MDW
$133
12/18Wed
nonstopUnited Airlines
3h 21mEYW-ORD
$140
2/19Wed
nonstopAmerican Airlines
3h 28mEYW-ORD
$150
2/23Sun
1 stop
14h 36mEYW-ORD
$156
1/1Wed
1 stopAmerican Airlines
5h 11mEYW-ORD
$159
12/17Tue
1 stopDelta
6h 23mEYW-ORD
$169
1/17Fri
1 stopUnited Airlines
8h 54mEYW-ORD
$190

Search by stops

Search by airline

Search by price

Last minute flights from Key West to Chicago

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 Key West to Chicago that are departing in the next 10 days.
11/22Fri
nonstopAmerican Airlines
3h 31mEYW-ORD
11/25Mon
nonstopAmerican Airlines
3h 16mORD-EYW
$349
11/22Fri
multi-stopAmerican Airlines
6h 54mEYW-ORD
11/25Mon
nonstopAmerican Airlines
3h 16mORD-EYW
$359
11/22Fri
multi-stopDelta
6h 46mEYW-ORD
11/25Mon
multi-stopDelta
5h 08mORD-EYW
$377
11/22Fri
multi-stopDelta
6h 21mEYW-MDW
11/25Mon
multi-stopDelta
6h 47mMDW-EYW
$377
11/22Fri
nonstopAmerican Airlines
3h 31mEYW-ORD
11/26Tue
multi-stopAmerican Airlines
5h 33mORD-EYW
$409
11/22Fri
multi-stopUnited Airlines
6h 59mEYW-ORD
11/25Mon
multi-stopUnited Airlines
28h 05mORD-EYW
$554
11/22Fri
multi-stopUnited Airlines
6h 59mEYW-ORD
11/26Tue
multi-stopUnited Airlines
11h 55mORD-EYW
$593
11/22Fri
multi-stop
24h 09mEYW-ORD
11/25Mon
multi-stop
27h 34mORD-EYW
$637
11/22Fri
nonstopAmerican Airlines
3h 31mEYW-ORD
11/26Tue
nonstopAmerican Airlines
3h 16mORD-EYW
$649
11/22Fri
multi-stopUnited Airlines
9h 54mEYW-ORD
11/26Tue
multi-stopUnited Airlines
8h 40mORD-EYW
$743

Search by stops

Search by airline

Search by price

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

Information on your arrival and departure airports

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