$144 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.

Fri, May 30 - Sun, Jun 1
EYW
Key West Intl.
ORD
O'Hare Intl.
$1,224 Roundtrip, found 1 day ago
$1,224
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, May 30 from Key West Intl. to O'Hare Intl., returning Sun, Jun 1, priced at $1,224 found 1 day ago

Airfares from $144 One Way, $289 Round Trip from Key West to Chicago

Prices starting at $289 for return flights and $144 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, Aug 28 - Mon, Sep 1
EYW
Key West
ORD
Chicago
$289 Roundtrip, found 3 days ago
$289
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Aug 28 from Key West to Chicago, returning Mon, Sep 1, priced at $289 found 3 days ago
Thu, Aug 28 - Mon, Sep 1
EYW
Key West
ORD
Chicago
$324 Roundtrip, found 3 days ago
$324
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Aug 28 from Key West to Chicago, returning Mon, Sep 1, priced at $324 found 3 days ago
Thu, Aug 28 - Mon, Sep 1
EYW
Key West
ORD
Chicago
$367 Roundtrip, found 3 days ago
$367
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Aug 28 from Key West to Chicago, returning Mon, Sep 1, priced at $367 found 3 days ago
Thu, Aug 28 - Mon, Sep 1
EYW
Key West
ORD
Chicago
$400 Roundtrip, found 3 days ago
$400
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Aug 28 from Key West to Chicago, returning Mon, Sep 1, priced at $400 found 3 days ago
Thu, Aug 28 - Mon, Sep 1
EYW
Key West
ORD
Chicago
$400 Roundtrip, found 3 days ago
$400
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Aug 28 from Key West to Chicago, returning Mon, Sep 1, priced at $400 found 3 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
1254 mi
Direct Flight Airlines
American Airlines, Qatar Airways
Earliest Flight Arrival
7:28PM UTC
Latest Flight Arrival
7:28PM UTC

Key West to Chicago

Orbitz is the number one travel site for finding guaranteed low prices on Key West to Chicago flights. Not only do we have discount tickets on domestic and international tickets but our cutting-edge mobile tools keep you informed on the go.

Find Low Prices in One Place

Booking a trip from Key West to Chicago has never been easier. Not only will you find great deals on flights, we offer bargains on cruises, car rentals, top-notch hotels, and more. You can also research and add local activities in Chicago to your flight or hotel reservation to keep the kids happy and active.

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Use our mobile app for your iPhone, iPad, or Android phone—or our mobile website m.orbitz.com—to find bargains on flights from Key West to Chicago wherever you are. Book your cheap Key West to Chicago flights and a hotel room too—even at the last minute. Orbitz also makes your life easier with free alerts that are sent to your mobile phone or email about delays to your upcoming flights from Key West to Chicago.

Don’t Miss out on Miles

Accumulate frequent flyer miles or points on your Key West to Chicago flights. It’s as simple as entering your frequent flyer number when you’re making your flight reservation on Orbitz to rack up miles on qualified flights from Key West to Chicago. You can save your frequent flyer numbers in your Orbitz account to save time during your next flight booking.

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.