$172 Cheap American Airlines flights from Key West to Chicago (EYW to ORD)

Find The Best Day To Fly from Key West to Chicago

Amazing American Airlines EYW to ORD Flight Deals

The cheapest flights to O'Hare Intl. found within the past 7 days were $347 round trip and $172 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Nov 7 - Mon, Nov 10
EYW
Key West
ORD
Chicago
$347 Roundtrip, found 7 hours ago
$347
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Nov 7 from Key West to Chicago, returning Mon, Nov 10, priced at $347 found 7 hours ago
Fri, Nov 7 - Mon, Nov 10
EYW
Key West
ORD
Chicago
$367 Roundtrip, found 7 hours ago
$367
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Nov 7 from Key West to Chicago, returning Mon, Nov 10, priced at $367 found 7 hours ago
Fri, Sep 19 - Sun, Sep 21
EYW
Key West
ORD
Chicago
$367 Roundtrip, found 1 day ago
$367
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Sep 19 from Key West to Chicago, returning Sun, Sep 21, priced at $367 found 1 day ago
Fri, Nov 7 - Mon, Nov 10
EYW
Key West
ORD
Chicago
$377 Roundtrip, found 7 hours ago
$377
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Nov 7 from Key West to Chicago, returning Mon, Nov 10, priced at $377 found 7 hours ago
Fri, Nov 7 - Mon, Nov 10
EYW
Key West
ORD
Chicago
$379 Roundtrip, found 7 hours ago
$379
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Nov 7 from Key West to Chicago, returning Mon, Nov 10, priced at $379 found 7 hours ago
Fri, Nov 7 - Mon, Nov 10
EYW
Key West
ORD
Chicago
$382 Roundtrip, found 7 hours ago
$382
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Nov 7 from Key West to Chicago, returning Mon, Nov 10, priced at $382 found 7 hours ago

Frequently asked questions

Can I catch a flight from EYW to ORD right now?
Make sure you visit our Covid-19 Travel Advisor to see if there are any present quarantine requirements and travel advice reports in place in ORD when flying from Key West Intl. Airport (EYW).
What terminal is American Airlines at EYW?
While we can't say for sure exactly which terminal your American Airlines flight from Key West Intl. Airport to ORD will take off from, we can tell you that you'll probably be stepping off the plane at terminal 3.
Are there American Airlines non-stop flights from EYW to ORD?
If you're going from Key West Intl. Airport to ORD and prefer to fly direct, American Airlines has you covered. Book your seat now and you'll be living it up at the other end before long.
How long is an American Airlines flight from EYW to ORD?
Weather and wind ... They're just a few things that can impact on how long your plane ride will last. However, a trip from Key West Intl. Airport (EYW) to ORD with American Airlines takes on average just 3 hours and 59 minutes, so you'll have touched down and be in vacation mode in the blink of an eye.
What type of aircraft does American Airlines fly from EYW to ORD?
If you're traveling from EYW to ORD with American Airlines, you'll likely be flying aboard the Embraer 175.
How many direct and indirect flights does American Airlines fly from EYW to ORD?
If you need to lock in a journey from EYW to ORD, you can pick from at least 2 American Airlines flights per day.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to ORD, please visit our Customer Service Portal.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Discover our best American Airlines flight from Key West EYW to Chicago ORD 

To find the best deals on flights to Key West from Chicago with American Airlines, just enter your travel dates, filter by American Airlines, and hit search. You’ll find flights to choose from and can sort by price, flight duration, and arrival or departure time.  

 

Return flights from Key West EYW to Chicago ORD with American Airlines 

If you’re planning a round trip, booking return flights with American Airlines is usually the most cost-effective option. With airfares ranging from $347 to $382, it’s easy to find a flight that suits your budget. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way American Airlines flights from Key West EYW to Chicago ORD 

A one-way ticket gives you much greater flexibility—allowing you to choose your return date, destination, and time whenever you’re ready. By booking in advance you can find great deals on one-way tickets too. Right now, a one-way American Airlines flight from Key West to Chicago costs from $172. Prices and availability subject to change. Additional terms may apply. 

 

The easy way to find cheap flights to Chicago ORD from  Key West EYW with American Airlines 

To find a cheap American Airlines flight from Key West EYW to Chicago ORD, sort your search results by price or filter by budget. Thanks to Travelocity’s Price Match Promise, if you find a better airfare deal anywhere else within 24 hours, we’ll credit or refund the difference. 

 

How to find our best airfare deals on American Airlines flights from Key West EYW to Chicago ORD 

If you’re looking for cheap flights, it helps to be flexible when it comes to your travel dates. You’ll usually find lower cost tickets when you travel during quieter months such as November, or if you book a flight with a stopover. 

 

Find nonstop flights from Key West EYW to Chicago ORD with American Airlines 

If you’re keen to be on Chicago soil fast, don’t waste time with a stopover—filter your search results to show direct American Airlines flights only. The journey takes around hour(s) min(s) – so you’ll be there before you know it. 

 

Flexible airline tickets for American Airlines flights from Key West EYW to Chicago ORD 

Make sure you’re not out of pocket if plans change by choosing a flexible ticket with penalty-free amendment and cancellation options. Use our ‘no change fee’ filter to see which flights have this option.  

 

There are a lot of reasons to book your flights to Chicago ORD from  Key West EYW with American Airlines on Travelocity 

At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether you’re traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.

American Airlines Airports
Hop on a(n) American Airlines flight today by flying to many destinations out of these domestic and international airports:
Airport code
Country
Airport name
Number of flights
DFWUSADallas-Fort Worth Intl.599
CLTUSACharlotte-Douglas Intl.536
ORDUSAO'Hare Intl.317
PHLUSAPhiladelphia Intl.247
MIAUSAMiami Intl.193
DCAUSARonald Reagan Washington National152
PHXUSASky Harbor Intl.141
LAXUSALos Angeles Intl.81
LGAUSALaGuardia72
BOSUSALogan Intl.57

Travelers ❤️ these 🏨 after their flight to Chicago

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...
8/10 Very Good! (2,090 reviews)
"Great"

Reviewed on Jul 27, 2025

Hilton Chicago O'Hare Airport
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd, Rosemont, IL
This hotel features 3 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free ...
8.6/10 Excellent! (2,353 reviews)
"The staff was very helpful."

Reviewed on Jul 28, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and ...
8.6/10 Excellent! (1,815 reviews)
"Our Church Archdiocese held its biennial convention at the Hyatt Regency O'Hare Hotel. Nobody could ask for anything more or better. The logistics for hosting over 2,000 registered guests must have been astronomical, but everything was there and in place when needed and expected. If/when I return ..."

Reviewed on Jul 29, 2025

Hyatt Regency O'Hare Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.