$154 Cheap flight deals from Key West (EYW) to Chicago (CHI)

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This Weekend's Flight Deals from Key West to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, May 4 - Thu, May 8
EYW
Key West Intl.
ORD
O'Hare Intl.
$881 Roundtrip, found 6 days ago
$881
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sun, May 4 from Key West Intl. to O'Hare Intl., returning Thu, May 8, priced at $881 found 6 days ago

Airfares from $154 One Way, $326 Round Trip from Key West to Chicago

Prices starting at $326 for return flights and $154 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.

Tue, Jul 29 - Sun, Aug 31
EYW
Key West
ORD
Chicago
$326 Roundtrip, found 1 day ago
$326
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 29 from Key West to Chicago, returning Sun, Aug 31, priced at $326 found 1 day ago
Tue, Jul 29 - Sun, Aug 31
EYW
Key West
ORD
Chicago
$354 Roundtrip, found 1 day ago
$354
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 29 from Key West to Chicago, returning Sun, Aug 31, priced at $354 found 1 day ago
Tue, Jul 29 - Sun, Aug 31
EYW
Key West
ORD
Chicago
$358 Roundtrip, found 1 day ago
$358
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 29 from Key West to Chicago, returning Sun, Aug 31, priced at $358 found 1 day ago
Tue, Jul 29 - Sun, Aug 31
EYW
Key West
ORD
Chicago
$362 Roundtrip, found 1 day ago
$362
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jul 29 from Key West to Chicago, returning Sun, Aug 31, priced at $362 found 1 day ago
Tue, Jul 29 - Sun, Aug 31
EYW
Key West
ORD
Chicago
$363 Roundtrip, found 1 day ago
$363
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 29 from Key West to Chicago, returning Sun, Aug 31, priced at $363 found 1 day 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
1254 mi
Direct Flight Airlines
American Airlines, Qatar Airways
Earliest Flight Arrival
7:33PM UTC
Latest Flight Arrival
7:33PM UTC

Key West to Chicago

Orbitz gives you great deals on your flights from Key West to Chicago. If you also need a discount car rental or a cheap hotel room after you arrived at your destination, Orbitz has you covered.

We Offer Great Travel Deals and Discounts

When you book flights from Key West to Chicago with Orbitz for, you can be assured that you are getting the lowest price possible. Orbitz works constantly with our airline partners to ensure guaranteed low prices on Key West to Chicago flights for your trip—whether you are traveling for business or for fun with your family.

Enjoy Savings on Last-Minute Flights

If you are looking for a discount price on last-minute flights from Key West to Chicago, chances are that Orbitz can offer you a deal that will save you lots of money. Whether you just want to get away for the weekend or go on a vacation lasting weeks, Orbitz can help you find the best deals on Key West to Chicago flights that fit your budget and your itinerary for the perfect trip.

Full-Service Mobile Apps

Need more mobility when it comes to travel planning? Orbitz has easy-to-use mobile apps for iPhone, iPad, and Android, to help the traveler on the go. Not only can use the apps to find huge savings on Key West to Chicago flights wherever you are, but you can also check out and book discount hotel rooms too. The apps will also keep you up-to-date when it’s time to fly. Get easy access to your itinerary for flights from Key West to Chicago and review gate and baggage claim details too.

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.

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.