$91 Cheap Flights from Key West (EYW) to Chicago (ORD)

View $91 flight on Tue, Feb 10, 2026Opens in a new window

Popular airlines from Key West Intl. Airport (EYW) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Key West to Chicago (EYW-ORD)

Prices were available within the past 7 days and start at $91 for one-way flights and $181 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Feb 18 - Wed, Feb 25
EYW
Key West
ORD
Chicago
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Feb 18 from Key West to Chicago, returning Wed, Feb 25, priced at $181 found 2 days ago
Spirit Airlines
Thu, Feb 19 - Tue, Feb 24
EYW
Key West
ORD
Chicago
$197 Roundtrip, found 15 hours ago
$197
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Thu, Feb 19 from Key West to Chicago, returning Tue, Feb 24, priced at $197 found 15 hours ago
Spirit Airlines
Thu, Feb 19 - Tue, Feb 24
EYW
Key West
ORD
Chicago
$198 Roundtrip, found 15 hours ago
$198
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Thu, Feb 19 from Key West to Chicago, returning Tue, Feb 24, priced at $198 found 15 hours ago
Spirit Airlines
Fri, Jan 9 - Wed, Jan 21
EYW
Key West
ORD
Chicago
$202 Roundtrip, found 4 days ago
$202
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, Jan 9 from Key West to Chicago, returning Wed, Jan 21, priced at $202 found 4 days ago
Spirit Airlines
Wed, Feb 18 - Sun, Feb 22
EYW
Key West
ORD
Chicago
$203 Roundtrip, found 8 hours ago
$203
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Wed, Feb 18 from Key West to Chicago, returning Sun, Feb 22, priced at $203 found 8 hours ago
Spirit Airlines
Mon, Jan 26 - Tue, Feb 3
EYW
Key West
ORD
Chicago
$210 Roundtrip, found 5 days ago
$210
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Jan 26 from Key West to Chicago, returning Tue, Feb 3, priced at $210 found 5 days ago
United
Thu, Feb 19 - Tue, Feb 24
EYW
Key West
ORD
Chicago
$249 Roundtrip, found 15 hours ago
$249
Roundtrip
found 15 hours ago
Select United flight, departing Thu, Feb 19 from Key West to Chicago, returning Tue, Feb 24, priced at $249 found 15 hours ago
American Airlines
Thu, Feb 19 - Tue, Feb 24
EYW
Key West
ORD
Chicago
$265 Roundtrip, found 15 hours ago
$265
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Thu, Feb 19 from Key West to Chicago, returning Tue, Feb 24, priced at $265 found 15 hours ago
Delta
Fri, Nov 21 - Mon, Dec 1
EYW
Key West
ORD
Chicago
$269 Roundtrip, found 2 hours ago
$269
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Nov 21 from Key West to Chicago, returning Mon, Dec 1, priced at $269 found 2 hours ago
JetBlue Airways
Thu, Dec 4 - Sun, Dec 7
EYW
Key West
ORD
Chicago
$523 Roundtrip, found 22 hours ago
$523
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Thu, Dec 4 from Key West to Chicago, returning Sun, Dec 7, priced at $523 found 22 hours ago

Find the cheapest month to fly from Key West (EYW) to Chicago (ORD)

January is typically the cheapest month to fly

From $208 - $685 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $289
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $289
Flights from Key West (EYW) to Chicago (ORD)
Origin airport
Key West Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, Spirit Airlines, United
Roundtrip price
$181
Distance
1254 mi

Key West to Chicago Flights

The cheapest times to fly from Key West to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Key West to Chicago are during the month of February. You can find some of the cheapest flights from Key West to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Key West to Chicago

Sunday is one of the best days to book for cheap flights from Key West to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Key West to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Key West to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $91 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Key West to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Key West to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $91 or cheap return flight from $181 from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from EYW to ORD is February, when there's less demand. Off-peak season is generally when airlines offer lower prices between these airports.
Which airlines fly direct from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
Catch a nonstop flight with American Airlines and go straight from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
The cheapest airline to offer flights between Key West Intl. Airport (EYW) and O'Hare Intl. Airport (ORD) can change depending on your travel plans. American Airlines and United Airlines are just some good options offering reasonable prices. Use Expedia's filters to compare airlines in one place and find the right EYW to ORD flight for your budget.
How many flights per day from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
When flying out of Key West Intl. Airport (EYW), you can pick from an average of 2 daily nonstop flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
The 3 PM departures from EYW to ORD are the most sought after. Greater demand means you'll likely pay more for these departures. If you're hoping to save money, pick a less crowded time to fly.
What day of the week has the most flights from EYW to ORD?
Friday offers the most flights from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD). Consider jetting off on this day and you'll have the best chance of finding a departure that works with your plans.
What is the earliest flight from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
Key West Intl. Airport (EYW)'s first flight to O'Hare Intl. Airport (ORD) is at approximately 1:06PM UTC-5. With a total travel time of 3h 31m, you'll arrive at around 3:37PM UTC-6.
How long does it take to fly from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
Flights from EYW to ORD have an average travel time of 3 hours and 31 minutes. The total distance between these two airports is 1,250 mi.
What airline has the least delays from EYW to ORD?
United Airlines has the best performance for on-time direct flights from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD), with an on-time rating of 81%. Use the Expedia App to see your journey status before you head off and receive notifications about any changes.
What is the best time to fly from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
Opt for a flight from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the risk of delays and cancellations. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Key West Intl. Airport (EYW)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Key West Intl. Airport (EYW). Check out the options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from EYW to ORD right before your trip is typically more expensive. But if there's some wiggle room with your departure dates and times, you could snag a cheap last-minute fare.
Is it cheaper to book an EYW to ORD flight and hotel package?
You'll generally save money by securing an EYW to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. Once you've selected your ideal accommodations and flights, consider adding extras including activities, car rentals and tours.
Can I cancel or change the date of my flight from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
If you booked your EYW to ORD flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

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*Available to One Key members.