$170 Cheap flights from Key West Intl. to O'Hare Intl. (EYW to ORD)

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Compare Flight Prices from Key West to Chicago

Affordable Airfare Tickets from EYW to ORD Airport

The cheapest flights to O'Hare Intl. found within the past 7 days were $323 round trip and $170 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Jul 9 - Tue, Jul 15
EYW
Key West
ORD
Chicago
$323 Roundtrip, found 6 hours ago
$323
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Jul 9 from Key West to Chicago, returning Tue, Jul 15, priced at $323 found 6 hours ago
Wed, Jul 9 - Tue, Jul 15
EYW
Key West
ORD
Chicago
$323 Roundtrip, found 6 hours ago
$323
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Jul 9 from Key West to Chicago, returning Tue, Jul 15, priced at $323 found 6 hours ago
Thu, Jul 10 - Wed, Jul 16
EYW
Key West
ORD
Chicago
$326 Roundtrip, found 6 hours ago
$326
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, Jul 10 from Key West to Chicago, returning Wed, Jul 16, priced at $326 found 6 hours ago
Wed, Jul 9 - Tue, Jul 15
EYW
Key West
ORD
Chicago
$328 Roundtrip, found 6 hours ago
$328
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Jul 9 from Key West to Chicago, returning Tue, Jul 15, priced at $328 found 6 hours ago
Wed, Jul 9 - Tue, Jul 15
EYW
Key West
ORD
Chicago
$347 Roundtrip, found 6 hours ago
$347
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Jul 9 from Key West to Chicago, returning Tue, Jul 15, priced at $347 found 6 hours ago
Thu, Jul 10 - Wed, Jul 16
EYW
Key West
ORD
Chicago
$351 Roundtrip, found 6 hours ago
$351
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, Jul 10 from Key West to Chicago, returning Wed, Jul 16, priced at $351 found 6 hours ago
Wed, Jul 9 - Tue, Jul 15
EYW
Key West
ORD
Chicago
$352 Roundtrip, found 6 hours ago
$352
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Jul 9 from Key West to Chicago, returning Tue, Jul 15, priced at $352 found 6 hours ago
Thu, Jul 10 - Wed, Jul 16
EYW
Key West
ORD
Chicago
$354 Roundtrip, found 6 hours ago
$354
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, Jul 10 from Key West to Chicago, returning Wed, Jul 16, priced at $354 found 6 hours ago
Wed, Jun 18 - Mon, Jun 23
EYW
Key West
ORD
Chicago
$357 Roundtrip, found 1 day ago
$357
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 18 from Key West to Chicago, returning Mon, Jun 23, priced at $357 found 1 day ago
Thu, Jul 10 - Wed, Jul 16
EYW
Key West
ORD
Chicago
$359 Roundtrip, found 6 hours ago
$359
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Thu, Jul 10 from Key West to Chicago, returning Wed, Jul 16, priced at $359 found 6 hours ago

Frequently asked questions

Can I catch a flight from EYW to O'Hare Intl. Airport (ORD) right now?
Make sure you visit the Covid-19 Travel Advisor to find out if there are any current travel advice reports and quarantine requirements in place in ORD when jet-setting from EYW.
Are there direct flights from Key West Intl. Airport to O'Hare Intl. Airport (ORD)?
Some trips are all about the journey; sometimes the magic is in the destination. If you’re keen to get to where you’re going fast, multiple airlines advertise direct flights from Key West Intl. Airport (EYW) to ORD, including United Airlines and American Airlines.
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 O’Hare Airport, please visit our Customer Service Portal.
How long is the flight from EYW to O'Hare Intl. Airport (ORD)?
Flights between Monroe County and Chicago take about 5 hours and 19 minutes all up. Make the most of your time in the air by napping, reading, watching a film or doing all three.
What is the flight distance from EYW to ORD?
There’s a flight distance of 1,250 mi separating EYW and O’Hare Airport. This is classified as a medium-haul flight. You’ll have lots of time to make the most of the in-flight entertainment and catch up on a snooze if you want to feel fresh on landing.
What airlines fly from Key West Intl. Airport to ORD?
There are several airlines that fly direct between Monroe County and Chicago. United Airlines (UA) is one of the most liked. This carrier operates approximately 30 flights each month. If you’d like more options, take a look at the deals on offer from American Airlines (AA). This airline operates 17 flights each month. Between the two, you’re sure to find a deal to suit your travel plans.
What airlines have practices regarding COVID-19 in place and use social distancing?
From the moment you enter the departure terminal to when you leave the arrivals terminal, if you’re flying with United Airlines, American Airlines or Delta you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.
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.

Flight information from Key West to Chicago

 

Traveling From
Key West Intl.
Traveling To
O'Hare Intl.
Shortest Flight Time
1 hours 39 mins
Earliest Departure Time
12:49PM CDT
Latest Departure Time
12:49PM CDT
Lowest Flight Price
$323

Route Info

Flight path for flights from Key West International Airport to O'Hare International Airport


Origin:
EYW - Key West International Airport
Destination:
ORD - O'Hare International Airport
Distance:
1,261.00 miles


Airlines & Aircraft Used on EYW to ORD Flight Routes


Airline Carrier
Aircraft
American Airlines
Boeing 737-800 (winglets) pax
American Airlines
Boeing 747-400 pax
United Airlines
Boeing 777 all pax models

Discover our best flights from Key West EYW to Chicago ORD. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Key West EYW to Chicago ORD at the right price  

Airfares to Chicago ORD from Key West EYW currently cost between $323 and $359. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

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

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Key West EYW to Chicago ORD on Travelocity starting at $170. Prices and availability subject to change. Additional terms may apply. 

 

Get to Chicago ORD from Key West EYW quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to ORD from EYW to take around 1 hour(s) 39 min(s).  

 

Find our cheapest airfares for flights from Key West EYW to Chicago ORD

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to ORD from EYW. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Key West EYW to Chicago ORD today 

If you’re flexible about when you travel, July is usually the cheapest month to fly from Key West EYW to Chicago ORD. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Chicago ORD from Key West EYW 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to ORD from EYW have this option.  

 

Travel with confidence when you book flights to Chicago ORD from Key West EYW with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*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.