$99 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, Jun 16 - Wed, Jun 26
EYW
Key West Intl.
ORD
O'Hare Intl.
$548 Roundtrip, found 6 days ago
$548
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Jun 16 from Key West Intl. to O'Hare Intl., returning Wed, Jun 26, priced at $548 found 6 days ago

Airfares from $99 One Way, $216 Round Trip from Key West to Chicago

Prices starting at $216 for return flights and $99 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, Sep 6 - Sat, Sep 7
EYW
Key West
ORD
Chicago
$216 Roundtrip, found 1 day ago
$216
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep 6 from Key West to Chicago, returning Sat, Sep 7, priced at $216 found 1 day ago
Fri, Sep 6 - Tue, Sep 10
EYW
Key West
ORD
Chicago
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep 6 from Key West to Chicago, returning Tue, Sep 10, priced at $232 found 1 day ago
Fri, Sep 6 - Tue, Sep 10
EYW
Key West
ORD
Chicago
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select United flight, departing Fri, Sep 6 from Key West to Chicago, returning Tue, Sep 10, priced at $248 found 1 day ago
Fri, Sep 6 - Tue, Sep 10
EYW
Key West
ORD
Chicago
$252 Roundtrip, found 1 day ago
$252
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep 6 from Key West to Chicago, returning Tue, Sep 10, priced at $252 found 1 day ago
Sat, Aug 17 - Wed, Aug 21
EYW
Key West
ORD
Chicago
$268 Roundtrip, just found
$268
Roundtrip
just found
Select Delta flight, departing Sat, Aug 17 from Key West to Chicago, returning Wed, Aug 21, priced at $268 just found

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

Low Cost Flights From 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.

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.