$96 Cheap flight deals from Key West (EYW) to Chicago (CHI)

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Airfares from $96 One Way, $191 Round Trip from Key West to Chicago

Prices starting at $191 for return flights and $96 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 21 - Wed, Jan 28
EYW
Key West
ORD
Chicago
$191 Roundtrip, found 5 days ago
$191
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Jan 21 from Key West to Chicago, returning Wed, Jan 28, priced at $191 found 5 days ago
Mon, Jan 26 - Wed, Feb 4
EYW
Key West
ORD
Chicago
$207 Roundtrip, found 3 days ago
$207
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Mon, Jan 26 from Key West to Chicago, returning Wed, Feb 4, priced at $207 found 3 days ago
Sat, Dec 6 - Sat, Dec 13
EYW
Key West
ORD
Chicago
$210 Roundtrip, found 2 days ago
$210
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Dec 6 from Key West to Chicago, returning Sat, Dec 13, priced at $210 found 2 days ago
Sat, Nov 22 - Sun, Nov 30
EYW
Key West
ORD
Chicago
$259 Roundtrip, found 4 days ago
$259
Roundtrip
found 4 days ago
Select United flight, departing Sat, Nov 22 from Key West to Chicago, returning Sun, Nov 30, priced at $259 found 4 days ago
Fri, Feb 6 - Wed, Feb 11
EYW
Key West
MDW
Chicago
$269 Roundtrip, found 4 days ago
$269
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Feb 6 from Key West to Chicago, returning Wed, Feb 11, priced at $269 found 4 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

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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.

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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.