Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap Flight Deals From Key West (EYW) to Chicago (CHI) Starting at $128

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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.

Airfares from $128 One Way, $245 Round Trip from Key West to Chicago

Prices starting at $245 for return flights and $128 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.

Chicago economy flight packages

The Godfrey Hotel Chicago
Best Western Grant Park Hotel
Residence Inn Chicago Downtown/Loop
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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 1254 mi
Direct Flight Airlines American Airlines, Qatar Airways, United Airlines
Earliest Flight Arrival 6:23PM UTC
Latest Flight Arrival 10:37PM UTC

Key West to Chicago

Getting a spectacularly low fare on Key West to Chicago flights is always possible when you use Orbitz as your personal travel planner. Orbitz is your essential travel resource for low cost flights from Key West to Chicago, discount hotel accommodations, cheap car rentals, and more.

Research and Book Key West to Chicago Flights on the Go

Our free cutting-edge mobile apps for iPad, Android, and iPhone make it easy to find the best fares when researching and booking flights from Key West to Chicago. You can also use the apps to check your flight status, find baggage claims details, and get exclusive mobile discount rates on car rentals and hotels.

Earn Miles and Points for Your Frequent Flyer Program

Build up points or miles for your frequent flyer plan with qualifying Key West to Chicago flights. Simply add your frequent flyer number when booking your domestic or international flights or enter the numbers in your Orbitz account profile to automatically add them to your bookings.

Flight Alerts Take the Hassle out of Travel

You can get email, SMS text, or voicemail updates regarding any major changes to your flights from Key West to Chicago. These free alerts can also be sent to as many as six additional contacts, ensuring that your friends, colleagues, or family are aware of changes to your arrival time.

Stay in Your Budget and Still Get Great Accommodations

Orbitz shoppers can access affordable vacation packages and have the option of booking their departure and arrival flights through different airlines, making travel less costly and more convenient. The best prices on flights from Key West to Chicagoare always found on Orbitz.

Flights from Key West to Chicago - Frequently Asked Questions

Am I able to catch a flight from Key West to Chicago now?

Our Covid-19 Travel Advisor can help you with questions about quarantine and travel restrictions when flying from Key West to Chicago.

Are there non-stop flights from Key West to Chicago?

Two carriers operate direct flights from Key West Intl. Airport to Chicago, IL Airport (ORD-O'Hare Intl.) — United Airlines and American Airlines. They'll get you where you need to go quickly and comfortably.

What is the shortest flight from Key West to Chicago?

The shortest flight from Key West, FL Airport (EYW-Key West Intl.) to Midway Airport is 3 hours and 42 minutes. Slip a few things into your hand luggage to keep you entertained, like that new best-seller or your travel journal.

What airlines fly from Key West to Chicago most frequently?

United Airlines (UA) operates 60 flights every month between Key West Intl. Airport (EYW) to ORD. Your next big adventure is just a few clicks away. American Airlines (AA) also operates services from Key West to Chicago. It's another excellent choice and offers 47 flights monthly.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

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 2020 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 the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2020. 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.