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EYW - CHI

$194 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 7/28. 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
Sat 6/15
Sat 6/22

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 42,211,976 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 Key West to Chicago (EYW-CHI)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Chicago 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
6:05 pm - 9:44 pmEYW-MDW
4h 39m1 stop
1:05 pm - 7:33 pmMDW-EYW
5h 28m1 stop
$232Delta
Find Deal
Fri, Sep 27 - Tue, Oct 1
2:35 pm - 7:01 pmEYW-ORD
5h 26m1 stop
6:00 am - 1:05 pmORD-EYW
6h 05m1 stop
$248Delta
Find Deal
Fri, Aug 16 - Sun, Aug 18
6:05 pm - 9:44 pmEYW-MDW
4h 39m1 stop
10:11 am - 5:09 pmMDW-EYW
5h 58m1 stop
$252Delta
Find Deal
Fri, Sep 27 - Tue, Oct 1
7:00 am - 2:12 pmEYW-ORD
8h 12m1 stop
6:00 am - 1:07 pmORD-EYW
6h 07m1 stop
$288Delta
Find Deal
Sat, Nov 9 - Mon, Nov 11
5:09 pm - 5:40 pmEYW-ORD
25h 31m2 stops
8:04 pm - 9:02 amORD-EYW
11h 58m1 stop
Thu, Jun 6 - Thu, Jun 13
2:40 pm - 9:37 pmEYW-ORD
7h 57m1 stop
8:30 am - 4:29 pmORD-EYW
6h 59m1 stop
$345American Airlines
Find Deal
Thu, Jun 20 - Mon, Jun 24
2:40 pm - 9:37 pmEYW-ORD
7h 57m1 stop
6:45 am - 1:55 pmORD-EYW
6h 10m1 stop
$347American Airlines
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Thu, Jun 20 - Mon, Jun 24
10:04 am - 12:55 amEYW-ORD
15h 51m3 stops
8:04 pm - 9:02 amORD-EYW
11h 58m1 stop
Thu, Jun 6 - Thu, Jun 13
4:00 pm - 6:24 pmEYW-ORD
3h 24mnonstop
10:40 am - 2:50 pmORD-EYW
3h 10mnonstop
$374United Airlines
Find Deal
Sat, Nov 9 - Mon, Nov 11
11:25 am - 9:47 amEYW-ORD
23h 22m1 stop
10:40 am - 2:50 pmORD-EYW
3h 10mnonstop
$404United Airlines
Find Deal
Sat, Nov 9 - Mon, Nov 11

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 $308 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 $914.

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 Friday 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 October, where tickets cost $255 on average. On the other hand, the most expensive months are November and February, where the average cost of tickets is $517 and $461 respectively.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Allegiant Air ($194) and United Airlines ($207). The cheapest round-trip tickets were found on Delta ($232) and American Airlines ($345).

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

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 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Key West to Chicago take?

There are no direct flights for this route listed on KAYAK. The shortest multi-flight duration is 3h 24m.

Good to know

Low season

January

High season

June
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 14% lower on average.

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 $194 for a one-way ticket and $232 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?

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

  • 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 $396 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

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 $351 or less one-way.

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 10673 reviews
7.9Comfort
8.2Boarding
8.6Crew
8.0Entertainment
7.4Food
Airline reviews

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

4.0 OkayJoanne, May 2024MIA - JFK
Read more about Delta reviews

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

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.
7/28Sun
1 stopAllegiant Air
15h 28mEYW-RFD
$194
6/25Tue
1 stopUnited Airlines
28h 32mEYW-ORD
$207
5/28Tue
1 stopUnited Airlines
28h 22mEYW-ORD
$214
7/21Sun
2 stops
19h 40mEYW-ORD
$245
6/8Sat
1 stopDelta
6h 56mEYW-ORD
$254
10/25Fri
1 stopAmerican Airlines
7h 21mEYW-ORD
$258
6/23Sun
2 stops
25h 31mEYW-ORD
$263
7/21Sun
1 stopDelta
7h 31mEYW-ORD
$279
6/22Sat
1 stopAmerican Airlines
5h 24mEYW-ORD
$293
6/25Tue
3 stopsAlaska Airlines
33h 15mEYW-ORD
$984

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Key West - Chicago Flights

Departure:

Key West (undefined)United States

Return flight deals:

Chicago - Key West

Cabin classes:

$2,708
$1,198
$714
$914