EYW - CHI

$113 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 10/8. 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

KAYAK searches 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
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Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Key West to Chicago

Fri, Sep 5 - Tue, Sep 9
United Airlines Logo
3:50 pm - 11:25 pmEYW-ORD
8h 35m1 stop
United Airlines Logo
6:00 am - 2:01 pmORD-EYW
7h 01m1 stop
$289United Airlines
Find Deal
Sat, Nov 15 - Sun, Nov 16
American Airlines Logo
8:00 am - 2:14 pmEYW-ORD
7h 14m1 stop
American Airlines Logo
8:30 am - 12:51 pmORD-EYW
3h 21mnonstop
$354American Airlines
Find Deal
Sat, Nov 15 - Sun, Nov 16
American Airlines Logo
12:40 pm - 7:18 pmEYW-ORD
7h 38m1 stop
American Airlines Logo
8:20 am - 4:12 pmORD-EYW
6h 52m1 stop
$364American Airlines
Find Deal
Sat, Nov 15 - Sun, Nov 16
Delta Logo
6:00 pm - 9:44 pmEYW-MDW
4h 44m1 stop
Delta Logo
1:05 pm - 7:44 pmMDW-EYW
5h 39m1 stop
$405Delta
Find Deal
Fri, Sep 5 - Tue, Sep 9
American Airlines Logo
1:59 pm - 6:13 pmEYW-ORD
5h 14m1 stop
American Airlines Logo
9:51 am - 6:59 pmORD-EYW
8h 08m2 stops
$419American Airlines
Find Deal
Sat, Nov 15 - Sun, Nov 16
American Airlines Logo
1:08 pm - 3:48 pmEYW-ORD
3h 40mnonstop
American Airlines Logo
8:30 am - 12:51 pmORD-EYW
3h 21mnonstop
$434American Airlines
Find Deal
Fri, Sep 5 - Tue, Sep 9
Delta Logo
7:00 am - 1:36 pmEYW-MDW
7h 36m1 stop
Delta Logo
6:00 am - 1:05 pmMDW-EYW
6h 05m1 stop
$464Delta
Find Deal
Sat, Nov 15 - Sun, Nov 16
United Airlines Logo
3:00 pm - 9:15 pmEYW-ORD
7h 15m1 stop
United Airlines Logo
9:25 pm - 2:04 pmORD-EYW
15h 39m2 stops
$510United Airlines
Find Deal
Fri, Sep 5 - Tue, Sep 9
United Airlines Logo
3:50 pm - 8:05 amEYW-ORD
17h 15m2 stops
United Airlines Logo
9:35 pm - 2:55 pmORD-EYW
16h 20m2 stops
$525United Airlines
Find Deal
Fri, Sep 5 - Tue, Sep 9
Delta Logo
7:00 am - 1:36 pmEYW-MDW
7h 36m1 stop
Delta Logo
6:00 am - 1:05 pmMDW-EYW
6h 05m1 stop
$544Delta
Find Deal
Expert advice

Expert advice for your flight from Key West to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
United Airlines

United's Economy Plus offers up to six inches more legroom than standard economy seats.


Purchase Priority Boarding to ensure overhead bin space and avoid gate-checking your carry-on.

American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks on longer flights.


Basic Economy offers low fares but includes restrictions like late boarding and no seat assignment.

Airports
EYW

Arrive two hours early at EYW for security. Lines can get long with only one security area and four lines available.

Read more about EYWby Paul Rubio
ORD

Take the CTA Blue Line from ORD to downtown Chicago. It's a 45-minute ride and avoids traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
Paul Rubio

Paul Rubio

Expert on EYW

Paul Rubio

Paul Rubio

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.

Read more
Booking Insights

KAYAK's insights & trends for Key West to Chicago flights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Key West to Chicago costs $199 on the route between Key West (EYW) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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

The average price of all round-trip flights from Key West to Chicago clicked on KAYAK for each day over the last 12 months.

When flying from Key West to Chicago, you should consider leaving on a Thursday and avoid Sundays if you are looking for the best rates. For your return to Key West, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

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

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.

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 $728 on average.

Good to know

Low seasonJune
Cheapest flight$113
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 2% lower on average.
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 $113 for a one-way ticket and $289 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 Embraer 170 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, SkyTeam, and Star Alliance are the airline alliances operating flights between Key West and Chicago, with SkyTeam being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Key West to Chicago are United Airlines and American Airlines. With an average price for the route of $442 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $379 and an overall rating of 7.2.

  • 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.

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 $373 or less one-way and $199 or less round-trip.

Prefer to fly direct from Key West to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Key West to Chicago.
Find which airlines fly direct from Key West Airport to Chicago, which days they fly and book direct flights.

Direct departures

Key West to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Key West

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top airlines flying 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.
7.4
United AirlinesOverall score based on 8928 reviews
8.1Crew
7.3Comfort
7.1Entertainment
6.6Food
7.7Boarding
Airline reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

2.0 MediocreAnonymous, Aug 2025RSW - ORD
Read more United Airlines reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

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

Information on your arrival and departure airports

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