EYW - ORD

$130 Find Cheap Flights from Key West to Chicago O'Hare Airport - Compare and Save

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 O'Hare Intl departing on 9/23. 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

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Everything you should know

Cheapest round-trip
$262
Multiple Airlines
Thu 9/3Mon 9/7
EYW - ORD • 1 stop
Cheapest non-stop
$312
American Airlines
Sat 9/5Sun 9/6
EYW - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds up to six inches more legroom than standard economy.
American Main Cabin Extra adds early boarding; use the AA app for entertainment.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $312 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 3h 51m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top layover airports
Cheapest • Avg $370 (round-trip)
Shortest trip • 5h 41m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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We hope you love your trip to O'Hare Intl!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Key West to O'Hare Intl (EYW-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to O'Hare Intl 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 O'Hare Intl

Thu, Sep 3 - Mon, Sep 7
Multiple Airlines Logo
12:05 pm - 11:08 pm
EYW
-
ORD
12h 03m
1 stop
Multiple Airlines Logo
8:05 am - 12:34 pm
ORD
-
EYW
27h 29m
2 stops
$262Multiple Airlines
Thu, Oct 1 - Sat, Oct 3
Multiple Airlines Logo
10:59 am - 10:59 pm
EYW
-
ORD
13h 00m
1 stop
Multiple Airlines Logo
3:50 pm - 2:13 pm
ORD
-
EYW
21h 23m
1 stop
$297Multiple Airlines
Thu, Sep 3 - Mon, Sep 7
Multiple Airlines Logo
12:05 pm - 11:08 pm
EYW
-
ORD
12h 03m
1 stop
Multiple Airlines Logo
8:05 am - 12:34 pm
ORD
-
EYW
27h 29m
2 stops
$309Multiple Airlines
Sat, Sep 5 - Sun, Sep 6
American Airlines Logo
4:56 pm - 7:48 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
12:08 pm - 4:27 pm
ORD
-
EYW
3h 19mnonstop
$312American Airlines
Thu, Sep 3 - Mon, Sep 7
American Airlines Logo
4:56 pm - 7:48 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
11:59 am - 4:18 pm
ORD
-
EYW
3h 19mnonstop
$319American Airlines
Thu, Sep 3 - Sun, Sep 6
American Airlines Logo
4:56 pm - 7:48 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
12:08 pm - 4:27 pm
ORD
-
EYW
3h 19mnonstop
$319American Airlines
Fri, Sep 4 - Sun, Sep 6
American Airlines Logo
4:56 pm - 7:48 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
12:08 pm - 4:27 pm
ORD
-
EYW
3h 19mnonstop
$319American Airlines
Sat, Sep 5 - Sun, Sep 6
American Airlines Logo
7:10 pm - 12:35 am
EYW
-
ORD
6h 25m
1 stop
American Airlines Logo
12:08 pm - 4:27 pm
ORD
-
EYW
3h 19mnonstop
$322American Airlines
Thu, Oct 1 - Sun, Oct 4
Multiple Airlines Logo
10:59 am - 11:55 pm
EYW
-
ORD
13h 56m
1 stop
Multiple Airlines Logo
3:50 pm - 8:34 am
ORD
-
EYW
15h 44m
1 stop
$328Multiple Airlines
Fri, Sep 4 - Sun, Sep 6
American Airlines Logo
4:50 pm - 11:52 pm
EYW
-
ORD
8h 02m
1 stop
American Airlines Logo
12:08 pm - 4:27 pm
ORD
-
EYW
3h 19mnonstop
$329American Airlines
Booking Insights

KAYAK's insights & trends for Key West to O'Hare Intl flights

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

How much is a round-trip flight from Key West to Chicago O'Hare Intl Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Key West to Chicago O'Hare Intl Airport departing in October.

Flight prices are below average for this route right now.

Flights to Chicago O'Hare Intl Airport from Key West usually cost between $353 and $409 in October.
The lowest price found in the past 5 days was $297 on Multiple Airlines (Oct 1-Oct 3).

What’s the cheapest day of the week to fly from Key West to Chicago O'Hare Airport?

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

If you are looking for a flight deal from Key West to Chicago O'Hare Airport, look for departures on Wednesdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago O'Hare Airport, Tuesday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Key West to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Key West to Chicago O'Hare Intl Airport, 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 O'Hare Intl Airport is March, where tickets cost $0 (return) on average. On the other hand, the most expensive months are January and April, where the average cost of round-trip tickets is $884 and $574 respectively.

Can I save money by flying with a layover from Key West to Chicago O'Hare Intl Airport?

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.

No, with an average price for the route of $339, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Key West to O'Hare Intl

 
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

Low season

December

Cheapest flight

$130
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Key West to Chicago O'Hare Airport

When to book flights from Key West to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Key West to O'Hare Intl 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 Key West to Chicago O'Hare Airport flights

  • What is the cheapest flight from Key West to Chicago O'Hare Intl Airport?

    In the last 5 days, the lowest price for a flight from Key West to Chicago O'Hare Intl Airport was $130 for a one-way ticket and $297 for a round-trip.

  • Do I need a passport to fly between Key West and Chicago O'Hare Airport?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

  • Which aircraft models fly most regularly from Key West to Chicago O'Hare Airport?

    The Embraer 170 is the aircraft model that flies most regularly on the Key West to Chicago O'Hare Airport flight route.

  • Which airline alliances offer flights from Key West to Chicago O'Hare Airport?

    oneworld is the only airline alliance operating flights between Key West and Chicago O'Hare Airport.

  • On which days can I fly direct from Key West to Chicago O'Hare Airport?

    There are nonstop flights from Key West to Chicago O'Hare Airport on a daily basis.

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

    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 O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport with an airline and back to Key West with another airline. Booking your flights between Key West and ORD can sometimes prove cheaper using this method.

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

    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 O'Hare Airport 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 O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $283 or less one-way and $446 or less round-trip.

Prefer to fly direct from Key West to Chicago O'Hare Airport?

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

Direct departures

Key West to Chicago O'Hare Intl

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 O'Hare Intl 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 O'Hare Intl

 
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 O'Hare Intl? 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 11837 reviews
7.2Comfort
6.4Food
7.9Crew
6.8Entertainment
7.5Boarding
Airline reviews

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

4.0 OkaySyeda, Jul 2026
MIA - ORD
Read more American Airlines reviews

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

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.

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.

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

Waited for oxygen tanks for 30 minutes after boarding was complete.

Little warm on the plane and delayed for an hour

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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

Everything you need to know for your flight from Key West to O'Hare Intl

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