$96 Cheap Flights from Key West (EYW) to Chicago (ORD)

View $96 flight on Tue, Jan 13, 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 $96 for one-way flights and $191 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Feb 3 - Tue, Feb 10
EYW
Key West
ORD
Chicago
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Feb 3 from Key West to Chicago, returning Tue, Feb 10, priced at $191 found 1 day ago
Spirit Airlines
Wed, Feb 11 - Wed, Feb 18
EYW
Key West
ORD
Chicago
$203 Roundtrip, found 3 days ago
$203
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Feb 11 from Key West to Chicago, returning Wed, Feb 18, priced at $203 found 3 days ago
Spirit Airlines
Sat, Dec 6 - Sat, Dec 13
EYW
Key West
ORD
Chicago
$207 Roundtrip, found 1 hour ago
$207
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Dec 6 from Key West to Chicago, returning Sat, Dec 13, priced at $207 found 1 hour ago
Spirit Airlines
Sat, Dec 6 - Sat, Dec 13
EYW
Key West
ORD
Chicago
$208 Roundtrip, found 1 hour ago
$208
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Dec 6 from Key West to Chicago, returning Sat, Dec 13, priced at $208 found 1 hour ago
Spirit Airlines
Fri, Feb 6 - Tue, Feb 10
EYW
Key West
ORD
Chicago
$212 Roundtrip, found 16 hours ago
$212
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Fri, Feb 6 from Key West to Chicago, returning Tue, Feb 10, priced at $212 found 16 hours ago
Spirit Airlines
Sun, Jan 11 - Tue, Jan 13
EYW
Key West
ORD
Chicago
$213 Roundtrip, found 18 hours ago
$213
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Sun, Jan 11 from Key West to Chicago, returning Tue, Jan 13, priced at $213 found 18 hours ago
United
Thu, Jan 8 - Mon, Jan 12
EYW
Key West
ORD
Chicago
$249 Roundtrip, found 10 hours ago
$249
Roundtrip
found 10 hours ago
Select United flight, departing Thu, Jan 8 from Key West to Chicago, returning Mon, Jan 12, priced at $249 found 10 hours ago
Delta
Fri, Jan 16 - Tue, Jan 20
EYW
Key West
ORD
Chicago
$269 Roundtrip, found 4 hours ago
$269
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Jan 16 from Key West to Chicago, returning Tue, Jan 20, priced at $269 found 4 hours ago
American Airlines
Tue, Mar 17 - Tue, Mar 31
EYW
Key West
ORD
Chicago
$303 Roundtrip, found 1 day ago
$303
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 17 from Key West to Chicago, returning Tue, Mar 31, priced at $303 found 1 day ago
JetBlue Airways
Sat, Nov 22 - Fri, Nov 28
EYW
Key West
ORD
Chicago
$688 Roundtrip, found 9 hours ago
$688
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Sat, Nov 22 from Key West to Chicago, returning Fri, Nov 28, priced at $688 found 9 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
$191
Distance
1254 mi
Average flight time
3 hours 46 mins

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 $96 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 $96 or cheap return flight from $191 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.