$214 Cheap flight deals from Key West (EYW) to Chicago (CHI)

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Airfares from $214 One Way, $409 Round Trip from Key West to Chicago

Prices starting at $409 for return flights and $214 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Feb 11 - Sat, Feb 13
EYW
Key West
ORD
Chicago
$409 Roundtrip, found 2 days ago
$409
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Feb 11 from Key West to Chicago, returning Sat, Feb 13, priced at $409 found 2 days ago
Thu, Feb 11 - Sat, Feb 13
EYW
Key West
ORD
Chicago
$435 Roundtrip, found 2 days ago
$435
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Feb 11 from Key West to Chicago, returning Sat, Feb 13, priced at $435 found 2 days ago
Thu, Feb 11 - Sat, Feb 13
EYW
Key West
ORD
Chicago
$445 Roundtrip, found 2 days ago
$445
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Feb 11 from Key West to Chicago, returning Sat, Feb 13, priced at $445 found 2 days ago
Thu, Dec 17 - Fri, Dec 25
EYW
Key West
ORD
Chicago
$447 Roundtrip, found 5 days ago
$447
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Dec 17 from Key West to Chicago, returning Fri, Dec 25, priced at $447 found 5 days ago
Thu, Feb 11 - Sat, Feb 13
EYW
Key West
ORD
Chicago
$457 Roundtrip, found 2 days ago
$457
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Feb 11 from Key West to Chicago, returning Sat, Feb 13, priced at $457 found 2 days ago

More About Flying To Chicago from Key West

Route Information for Flights from Key West to Chicago

Origin Airport IATA Code
EYW
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Key West to Chicago

Orbitz guarantees you low prices on flights from Key West to Chicago. In addition to low fares on Key West to Chicago flights, Orbitz offers fantastic savings on hotels, cruises, vacation packages, and more.

Earn Miles While Saving

Besides helping you fly for the lowest fares, Orbitz lets you earn miles for your frequent flyer program for certain flights from Key West to Chicago. If you are a member of the frequent flyer or loyalty program offered by the airline you booked through Orbitz or a partner airline’s, simply add your frequent flyer number to your Orbitz reservation to get credit for your Key West to Chicago flights.

Travel Planning Made Easy

We help take some of the anxiety out of your Key West to Chicago flights with free flight alerts. We will let you know of flight changes and delays to your flights from Key West to Chicago by email, voicemail, or text messages to your mobile phone. Alerts can also be sent to up to six other contacts to keep family and business teams informed.

Use Mobile Apps with Orbitz

Orbitz lets you find the best deals on Key West to Chicago flights while on the go, with our easy-to-use Android and iPhone mobile apps. Easily check flight status, gate numbers, and other flight details all in one place with our app—which is great when you are in a hurry. You can use the apps to access great mobile deals on flights and amazing hotel rooms.

Frequently asked questions

Are there non-stop flights from Key West to Chicago?
The terrific news is, there are. United Airlines and American Airlines are a couple of carriers that will fly you directly from Key West, FL (EYW-Key West Intl.) to ORD.
What is the shortest flight from Key West to Chicago?
The fastest flight from Key West Intl. Airport to Chicago, IL (ORD-O'Hare Intl.) is 3 hours and 43 minutes. Pack a few things in your carry-on to help pass the time, like a gripping read or a portable board game.
What airlines fly from Key West to Chicago most frequently?
United Airlines (UA) is one of the carriers with the most flights from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD). It offers 30 flights on this route each month. Taking a vacation is one of life's greatest pleasures, and this airline will get you to your destination quickly and safely. If you'd like some more options, check out the fares with American Airlines (AA), which offers 17 flights from Key West to Chicago every month.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.