$123 Cheap flight deals from Key West (EYW) to Chicago (CHI)

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Airfares from $123 One Way, $243 Round Trip from Key West to Chicago

Prices starting at $243 for return flights and $123 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.

Wed, Jan 28 - Wed, Feb 4
EYW
Key West
ORD
Chicago
$243 Roundtrip, found 2 days ago
$243
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jan 28 from Key West to Chicago, returning Wed, Feb 4, priced at $243 found 2 days ago
Thu, Jan 22 - Tue, Jan 27
EYW
Key West
ORD
Chicago
$244 Roundtrip, found 17 hours ago
$244
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Thu, Jan 22 from Key West to Chicago, returning Tue, Jan 27, priced at $244 found 17 hours ago
Thu, Nov 6 - Thu, Nov 13
EYW
Key West
ORD
Chicago
$245 Roundtrip, found 3 hours ago
$245
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Thu, Nov 6 from Key West to Chicago, returning Thu, Nov 13, priced at $245 found 3 hours ago
Wed, Jan 21 - Mon, Jan 26
EYW
Key West
ORD
Chicago
$254 Roundtrip, found 17 hours ago
$254
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Wed, Jan 21 from Key West to Chicago, returning Mon, Jan 26, priced at $254 found 17 hours ago
Fri, Nov 14 - Sun, Nov 16
EYW
Key West
ORD
Chicago
$255 Roundtrip, found 3 days ago
$255
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Fri, Nov 14 from Key West to Chicago, returning Sun, Nov 16, priced at $255 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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Key West to Chicago

If you feel you cannot afford the costs involved to your dream trip to a local or international destination happen, think again! Orbitz gives you incredible deals on flights from Key West to Chicago. Now you can book guaranteed low fares for Key West to Chicago flights and plan your trip with confidence.

Great deals on flights from Key West to Chicago

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Key West to Chicago flights at discounted rates

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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.