$102 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, Jan 18 - Wed, Jan 28
EYW
Key West Intl.
ORD
O'Hare Intl.
$415 Roundtrip, found 3 days ago
$415
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Jan 18 from Key West Intl. to O'Hare Intl., returning Wed, Jan 28, priced at $415 found 3 days ago

Airfares from $102 One Way, $192 Round Trip from Key West to Chicago

Prices starting at $192 for return flights and $102 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 5 - Sun, Feb 8
EYW
Key West
ORD
Chicago
$192 Roundtrip, found 3 days ago
$192
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Feb 5 from Key West to Chicago, returning Sun, Feb 8, priced at $192 found 3 days ago
Thu, Feb 26 - Mon, Mar 2
EYW
Key West
ORD
Chicago
$192 Roundtrip, found 6 days ago
$192
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Thu, Feb 26 from Key West to Chicago, returning Mon, Mar 2, priced at $192 found 6 days ago
Thu, Jan 29 - Sun, Feb 1
EYW
Key West
ORD
Chicago
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Jan 29 from Key West to Chicago, returning Sun, Feb 1, priced at $206 found 1 day ago
Thu, Feb 12 - Thu, Feb 19
EYW
Key West
ORD
Chicago
$228 Roundtrip, found 2 days ago
$228
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Feb 12 from Key West to Chicago, returning Thu, Feb 19, priced at $228 found 2 days ago
Thu, Feb 12 - Sun, Feb 15
EYW
Key West
ORD
Chicago
$236 Roundtrip, found 5 days ago
$236
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Thu, Feb 12 from Key West to Chicago, returning Sun, Feb 15, priced at $236 found 5 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

Whether you want to book cheap flights from Key West to Chicago or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Key West to Chicago flights.

Make the Most of Your Vacation

Not only does Orbitz have cheap deals for Key West to Chicago flights, we can also help you plan your vacation in advance. Why wait in lengthy lines for tickets to shows, amusement parks, and other attractions when you could be making the most of your holiday? Add activities to your flight booking for fewer hassles once you arrive in Chicago.

Planning on the Go

Book your flights from Key West to Chicago wherever you are with the Orbitz app for Android and iPhone. Or simply use m.orbitz.com on your mobile browser to search and book the Key West to Chicago flights that you want. And if you’re running late, you check your flight status and baggage claim information on your mobile device too too.

Craft Your Perfect Vacation

Orbitz takes the stress out of vacation planning with great deals on flights from Key West to Chicago, hotels, car rentals, cruises, and more. Mix and match results for your perfect trip, or book a complete vacation package.

Keep Informed With Orbitz

With Orbitz’s free alerts service, you will stay informed of flight or services disruptions to your Key West to Chicago flights. The alerts can be sent straight to your mobile phone or email.

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.