EYW - CHI

$103 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 5/19. 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, 0 bags

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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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

Everything you should know

Cheapest round-trip
$237
Typical prices: $427-$388
Multiple Airlines
Thu 5/14Sun 5/24
EYW - ORD • 1 stop
Cheapest non-stop
$309
United Airlines
Thu 5/14Sun 5/17
EYW - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers more legroom than standard.
Arrive two hours early at Key West for security lines.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $309 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 3h 51m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $298 (round-trip)
Shortest trip • 5h 32m (one-way)
Insights
Insights
Insights
Insights
Start a new search
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
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

Thu, May 14 - Sun, May 24
Multiple Airlines Logo
3:08 pm - 12:23 pm
EYW
-
ORD
22h 15m
1 stop
Multiple Airlines Logo
1:50 pm - 12:31 pm
ORD
-
EYW
21h 41m
2 stops
$237Multiple Airlines
Wed, May 6 - Sun, May 10
Multiple Airlines Logo
11:46 am - 9:27 am
EYW
-
ORD
22h 41m
1 stop
Multiple Airlines Logo
8:30 am - 12:31 pm
ORD
-
EYW
27h 01m
1 stop
$243Multiple Airlines
Fri, May 8 - Fri, May 15
Multiple Airlines Logo
1:11 pm - 12:23 pm
EYW
-
ORD
24h 12m
1 stop
Multiple Airlines Logo
1:59 pm - 11:04 am
ORD
-
EYW
20h 05m
2 stops
$248Multiple Airlines
Thu, May 14 - Sun, May 17
Multiple Airlines Logo
1:57 pm - 10:14 pm
EYW
-
ORD
9h 17m
1 stop
Multiple Airlines Logo
5:30 pm - 11:27 am
ORD
-
EYW
16h 57m
1 stop
$267Multiple Airlines
Thu, May 14 - Sun, May 17
Multiple Airlines Logo
1:57 pm - 10:14 pm
EYW
-
ORD
9h 17m
1 stop
Multiple Airlines Logo
8:39 am - 11:27 am
ORD
-
EYW
25h 48m
2 stops
$277Multiple Airlines
Wed, Jun 3 - Sat, Jun 6
Multiple Airlines Logo
11:46 am - 7:51 pm
EYW
-
ORD
9h 05m
2 stops
Multiple Airlines Logo
5:11 pm - 11:25 am
ORD
-
EYW
17h 14m
1 stop
$279Multiple Airlines
Wed, May 6 - Sun, May 10
Multiple Airlines Logo
11:46 am - 9:27 am
EYW
-
ORD
22h 41m
1 stop
Multiple Airlines Logo
1:59 pm - 11:27 am
ORD
-
EYW
20h 28m
2 stops
$282Multiple Airlines
Wed, May 27 - Wed, Jun 10
Multiple Airlines Logo
11:46 am - 7:55 am
EYW
-
ORD
21h 09m
2 stops
Multiple Airlines Logo
5:25 pm - 11:25 am
ORD
-
EYW
17h 00m
1 stop
$289Multiple Airlines
Tue, May 5 - Sat, May 9
Delta Logo
6:23 pm - 10:28 pm
EYW
-
MDW
5h 05m
1 stop
Delta Logo
6:23 am - 2:35 pm
MDW
-
EYW
7h 12m
1 stop
$389Delta
Fri, May 8 - Tue, May 12
Delta Logo
7:30 am - 11:56 am
EYW
-
MDW
5h 26m
1 stop
Delta Logo
10:59 am - 5:23 pm
MDW
-
EYW
5h 24m
1 stop
$424Delta
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 $339 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 Wednesday and avoid Mondays 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 $372 on average.

Expert advice

Expert advice for your flight from Key West to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

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.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Paul Rubio

Paul Rubio

Expert on EYW

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.

Good to know

Cheapest flight$99
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 $99 for a one-way ticket and $237 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?

    Star Alliance, and oneworld are the airline alliances operating flights between Key West and Chicago, with Star Alliance 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.

  • 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 $333 or less one-way and $479 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

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

Chicago to Key West

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Reviews of the top airline 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.
7.1
American AirlinesOverall score based on 11659 reviews
7.9Crew
7.5Boarding
6.9Entertainment
6.4Food
7.2Comfort
Airline reviews

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

10.0 ExcellentDeepa, Apr 2026
DFW - ORD
Read more American Airlines reviews

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

I have never been assaulted they way I was today in Charlotte - shame on American

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

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

Information on your arrival and departure airports