EYW - ORD

$105 Find Cheap Flights from Key West to Chicago O'Hare Airport

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 4/17. 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 O'Hare Intl Airport

 
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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Everything you should know

Cheapest round-trip
$271
Overall average: $499
Multiple Airlines
Wed 4/15Wed 4/22
EYW - ORD • 2 stops
Cheapest non-stop
$289
American Airlines
Thu 4/9Mon 4/13
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 extra legroom on this route.
Arrive two hours early at Key West for security checks.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $289 (round-trip)
Best reviews • 7.4 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 47m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
Cheapest • 40% 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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Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
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

Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
11:51 am - 10:23 am
EYW
-
ORD
23h 32m
2 stops
Multiple Airlines Logo
8:52 pm - 3:42 pm
ORD
-
EYW
17h 50m
1 stop
$271Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
6:46 pm - 9:35 pm
EYW
-
ORD
3h 49mnonstop
American Airlines Logo
8:10 am - 12:38 pm
ORD
-
EYW
3h 28mnonstop
$289American Airlines
Sun, Apr 5 - Sat, Apr 11
Multiple Airlines Logo
10:32 pm - 10:39 pm
EYW
-
ORD
49h 07m
2 stops
Multiple Airlines Logo
6:10 pm - 11:30 am
ORD
-
EYW
16h 20m
1 stop
$290Multiple Airlines
Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
11:51 am - 3:08 pm
EYW
-
ORD
28h 17m
1 stop
Multiple Airlines Logo
8:52 pm - 3:42 pm
ORD
-
EYW
17h 50m
1 stop
$292Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
8:05 am - 3:21 pm
EYW
-
ORD
8h 16m
1 stop
American Airlines Logo
8:10 am - 12:38 pm
ORD
-
EYW
3h 28mnonstop
$299American Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
8:05 am - 3:21 pm
EYW
-
ORD
8h 16m
1 stop
American Airlines Logo
3:26 pm - 10:36 pm
ORD
-
EYW
6h 10m
1 stop
$309American Airlines
Wed, Apr 15 - Wed, Apr 22
United Airlines Logo
3:52 pm - 6:36 pm
EYW
-
ORD
3h 44mnonstop
United Airlines Logo
7:30 am - 3:57 pm
ORD
-
EYW
7h 27m
1 stop
$319United Airlines
Tue, Mar 31 - Sat, Apr 4
Multiple Airlines Logo
1:01 pm - 6:26 pm
EYW
-
ORD
6h 25m
1 stop
Multiple Airlines Logo
7:17 am - 10:21 am
ORD
-
EYW
26h 04m
2 stops
$333Multiple Airlines
Tue, Mar 31 - Sat, Apr 4
Multiple Airlines Logo
1:01 pm - 6:26 pm
EYW
-
ORD
6h 25m
1 stop
Multiple Airlines Logo
6:10 pm - 11:30 am
ORD
-
EYW
16h 20m
1 stop
$337Multiple Airlines
Fri, Apr 3 - Fri, Apr 10
Multiple Airlines Logo
1:06 pm - 12:04 am
EYW
-
ORD
11h 58m
2 stops
Multiple Airlines Logo
5:05 am - 1:37 pm
ORD
-
EYW
7h 32m
1 stop
$354Multiple 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.

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 Sunday, 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 December, where tickets cost $268 (return) on average. On the other hand, the most expensive months are January and March, where the average cost of round-trip tickets is $884 and $650 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 $349, 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
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.

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.

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 seasonJanuary
Cheapest flight$105
Best time to beat the crowds but there is an average 96% increase in price.
Most popular time to fly with an average 25% 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 3 days, the lowest price for a flight from Key West to Chicago O'Hare Intl Airport was $105 for a one-way ticket and $271 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?

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

  • 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.

  • 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 $315 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 $457 and an overall rating of 7.1.

  • 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 $310 or less one-way and $349 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 airlines 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.
7.4
United AirlinesOverall score based on 9428 reviews
7.7Boarding
7.3Comfort
8.1Crew
7.1Entertainment
6.6Food
Airline reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

10.0 ExcellentDr. Joseph, Feb 2026
DCA - ORD
Read more United Airlines reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

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

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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

Information on your arrival and departure airports