$156 Cheap flight deals from Key West (EYW) to Chicago (CHI)

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Airfares from $156 One Way, $364 Round Trip from Key West to Chicago

Prices starting at $364 for return flights and $156 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.

Sat, Aug 30 - Mon, Sep 1
EYW
Key West
ORD
Chicago
$364 Roundtrip, found 4 days ago
$364
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Aug 30 from Key West to Chicago, returning Mon, Sep 1, priced at $364 found 4 days ago
Sat, Aug 30 - Mon, Sep 1
EYW
Key West
ORD
Chicago
$371 Roundtrip, found 4 days ago
$371
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Aug 30 from Key West to Chicago, returning Mon, Sep 1, priced at $371 found 4 days ago
Thu, May 15 - Sat, May 17
EYW
Key West
MDW
Chicago
$376 Roundtrip, found 2 days ago
$376
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, May 15 from Key West to Chicago, returning Sat, May 17, priced at $376 found 2 days ago
Sat, Aug 30 - Mon, Sep 1
EYW
Key West
ORD
Chicago
$383 Roundtrip, found 4 days ago
$383
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Aug 30 from Key West to Chicago, returning Mon, Sep 1, priced at $383 found 4 days ago
Sat, Aug 30 - Mon, Sep 1
EYW
Key West
ORD
Chicago
$385 Roundtrip, found 4 days ago
$385
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Aug 30 from Key West to Chicago, returning Mon, Sep 1, priced at $385 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

It has never been easier to find cheap Key West to Chicago flights. Orbitz has some of the best deals around to save you more money on your flight, hotel, and vacation package for the trip you have been waiting for.

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Get the Best Deals on Key West to Chicago Flights

Finding great deals on flights from Key West to Chicago is a snap with Orbitz. With our guaranteed low prices, you don’t have to worry if you are getting the best prices on air tickets, hotels, and cruises. And with all that money you saved, you can enjoy your Chicago vacation even more.

Pile Up Miles With Discount Air Tickets

Not only can you find great bargains on Key West to Chicago flights, but you can rack up frequent flyer miles on the flights too. Enter your frequent flyer number on qualified flights when booking for Orbitz to see the miles pile up in your account.

Flight Alerts Keep You Informed

Stay on top of the latest updates for flights from Key West to Chicago. We send you free email and mobile alerts to keep you informed about delays to Key West to Chicago flights.

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.