$189 Cheap flight deals from Key West (EYW) to Chicago (CHI)

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Airfares from $189 One Way, $316 Round Trip from Key West to Chicago

Prices starting at $316 for return flights and $189 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.

Fri, May 15 - Mon, May 18
EYW
Key West
ORD
Chicago
$316 Roundtrip, found 6 days ago
$316
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 15 from Key West to Chicago, returning Mon, May 18, priced at $316 found 6 days ago
Fri, May 15 - Mon, May 18
EYW
Key West
ORD
Chicago
$326 Roundtrip, found 6 days ago
$326
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 15 from Key West to Chicago, returning Mon, May 18, priced at $326 found 6 days ago
Fri, May 15 - Mon, May 18
EYW
Key West
ORD
Chicago
$336 Roundtrip, found 6 days ago
$336
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 15 from Key West to Chicago, returning Mon, May 18, priced at $336 found 6 days ago
Fri, May 15 - Mon, May 18
EYW
Key West
ORD
Chicago
$351 Roundtrip, found 6 days ago
$351
Roundtrip
found 6 days ago
Select United flight, departing Fri, May 15 from Key West to Chicago, returning Mon, May 18, priced at $351 found 6 days ago
Fri, May 15 - Mon, May 18
EYW
Key West
ORD
Chicago
$385 Roundtrip, found 6 days ago
$385
Roundtrip
found 6 days ago
Select United flight, departing Fri, May 15 from Key West to Chicago, returning Mon, May 18, priced at $385 found 6 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

Getting a spectacularly low fare on Key West to Chicago flights is always possible when you use Orbitz as your personal travel planner. Orbitz is your essential travel resource for low cost flights from Key West to Chicago, discount hotel accommodations, cheap car rentals, and more.

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Our free cutting-edge mobile apps for iPad, Android, and iPhone make it easy to find the best fares when researching and booking flights from Key West to Chicago. You can also use the apps to check your flight status, find baggage claims details, and get exclusive mobile discount rates on car rentals and hotels.

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Build up points or miles for your frequent flyer plan with qualifying Key West to Chicago flights. Simply add your frequent flyer number when booking your domestic or international flights or enter the numbers in your Orbitz account profile to automatically add them to your bookings.

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You can get email, SMS text, or voicemail updates regarding any major changes to your flights from Key West to Chicago. These free alerts can also be sent to as many as six additional contacts, ensuring that your friends, colleagues, or family are aware of changes to your arrival time.

Stay in Your Budget and Still Get Great Accommodations

Orbitz shoppers can access affordable vacation packages and have the option of booking their departure and arrival flights through different airlines, making travel less costly and more convenient. The best prices on flights from Key West to Chicagoare always found on Orbitz.

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.