EYW - ORD

$84 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 2/27. 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
$214
Multiple Airlines
Tue 2/24Tue 3/3
EYW - ORD • 1 stop
Cheapest non-stop
$249
American Airlines
Thu 4/9Mon 4/13
EYW - ORD • Non-stop
Our travelers' advice
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
American Airlines
Cheapest • from $249 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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

Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
1:01 pm - 5:03 pm
EYW
-
ORD
29h 02m
1 stop
Multiple Airlines Logo
6:51 pm - 9:06 am
ORD
-
EYW
37h 15m
2 stops
$214Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
1:01 pm - 5:03 pm
EYW
-
ORD
29h 02m
1 stop
Multiple Airlines Logo
10:19 am - 11:50 am
ORD
-
EYW
24h 31m
1 stop
$229Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
6:45 pm - 9:37 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
1:51 pm - 6:15 pm
ORD
-
EYW
3h 24mnonstop
$249American Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
6:35 pm - 11:43 pm
EYW
-
ORD
6h 08m
1 stop
United Airlines Logo
10:44 am - 3:00 pm
ORD
-
EYW
3h 16mnonstop
$259United Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
6:35 pm - 11:43 pm
EYW
-
ORD
6h 08m
1 stop
United Airlines Logo
7:10 am - 5:44 pm
ORD
-
EYW
9h 34m
1 stop
$269United Airlines
Fri, May 29 - Wed, Jun 3
Multiple Airlines Logo
2:51 pm - 7:59 am
EYW
-
ORD
18h 08m
1 stop
Multiple Airlines Logo
10:17 am - 3:22 pm
ORD
-
EYW
28h 05m
1 stop
$271Multiple Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
3:56 pm - 6:35 pm
EYW
-
ORD
3h 39mnonstop
United Airlines Logo
10:44 am - 3:00 pm
ORD
-
EYW
3h 16mnonstop
$279United Airlines
Sun, May 31 - Wed, Jun 3
Multiple Airlines Logo
4:10 pm - 5:10 pm
EYW
-
ORD
26h 00m
1 stop
Multiple Airlines Logo
3:49 pm - 11:25 am
ORD
-
EYW
18h 36m
1 stop
$282Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
American Airlines Logo
6:34 pm - 12:06 am
EYW
-
ORD
6h 32m
1 stop
American Airlines Logo
1:59 pm - 6:24 pm
ORD
-
EYW
3h 25mnonstop
$289American Airlines
Mon, Jun 1 - Wed, Jun 3
Multiple Airlines Logo
12:10 pm - 7:59 am
EYW
-
ORD
20h 49m
1 stop
Multiple Airlines Logo
10:17 am - 10:24 am
ORD
-
EYW
23h 07m
1 stop
$299Multiple 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 Thursdays 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.

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 $434, 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 seasonDecember
Cheapest flight$84
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly and prices are also 20% lower on average.
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 $84 for a one-way ticket and $214 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 $367 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 $427 and an overall rating of 7.2.

  • 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 $346 or less one-way and $413 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 9215 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
8.1Crew
6.6Food
Airline reviews

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.

4.0 OkaySean, Jan 2026
BOS - ORD
Read more United Airlines reviews

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

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

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

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

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