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

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

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
    trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash

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
Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
United
American Airlines
Delta
JetBlue Airways

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.

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.

Travel information

Travel information

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

Book with confidence

Book with confidence

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.