$109 Cheap flight deals from Chicago (CHI) to Key West (EYW)

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This Weekend's Flight Deals from Chicago to Key West

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.

Sat, May 11 - Sun, May 26
ORD
O'Hare Intl.
EYW
Key West Intl.
$313 Roundtrip, found 1 day ago
$313
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 11 from O'Hare Intl. to Key West Intl., returning Sun, May 26, priced at $313 found 1 day ago
Sat, May 11 - Tue, May 14
MDW
Midway Intl.
EYW
Key West Intl.
$343 Roundtrip, found 2 days ago
$343
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, May 11 from Midway Intl. to Key West Intl., returning Tue, May 14, priced at $343 found 2 days ago

Airfares from $109 One Way, $216 Round Trip from Chicago to Key West

Prices starting at $216 for return flights and $109 for one-way flights to Key West were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jun 18 - Wed, Jun 26
ORD
Chicago
EYW
Key West
$216 Roundtrip, found 3 days ago
$216
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 18 from Chicago to Key West, returning Wed, Jun 26, priced at $216 found 3 days ago
Tue, Jul 16 - Tue, Jul 30
ORD
Chicago
EYW
Key West
$226 Roundtrip, found 1 day ago
$226
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 16 from Chicago to Key West, returning Tue, Jul 30, priced at $226 found 1 day ago
Wed, Jul 17 - Thu, Jul 25
ORD
Chicago
EYW
Key West
$232 Roundtrip, found 4 days ago
$232
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jul 17 from Chicago to Key West, returning Thu, Jul 25, priced at $232 found 4 days ago
Tue, Jul 16 - Mon, Aug 5
ORD
Chicago
EYW
Key West
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 16 from Chicago to Key West, returning Mon, Aug 5, priced at $237 found 1 day ago
Tue, Nov 12 - Tue, Nov 19
ORD
Chicago
EYW
Key West
$245 Roundtrip, found 2 days ago
$245
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Nov 12 from Chicago to Key West, returning Tue, Nov 19, priced at $245 found 2 days ago

Key West economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West
3.5-star property

Hyatt Vacation Club at Beach House, Key West

9.2/10 Wonderful! (667 reviews)

Jun 9 - Jun 14

5 night stay

Chicago (ORD) to Key West (EYW)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
per person
Pros: Our room was clean and well-appointed. The staff was friendly and informed of various things we could do on the island. Cons: The facility's late checkout is 10am which isn't convenient for the late afternoon and evening flights. In hindsight I would have scheduled an earlier flight out, however, we made good use of the time by taking the hop-on/hop-off tour around the island until it was time to check in at the airport.

Reviewed on Jan 1, 2024

Pier House Resort & Spa
4.0-star property

Pier House Resort & Spa

8.8/10 Excellent! (1,003 reviews)

Jun 24 - Jun 29

5 night stay

Chicago (MDW) to Key West (EYW)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
per person
Great stay! So close to everything but set back and quiet on the property

Reviewed on Apr 9, 2024

Orchid Key Inn - Adults Only
3.5-star property

Orchid Key Inn - Adults Only

9.8/10 Exceptional! (1,000 reviews)

Jun 24 - Jun 29

5 night stay

Chicago (MDW) to Key West (EYW)

Delta • Non-stop roundtrip • Coach
per person
Very cute and close to everything. Great place to have a scooter to park and get in and out easy. Great bar and staff. They make a strong drink.

Reviewed on Jun 23, 2023

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More About Flying To Key West from Chicago

Route Information for Flights from Chicago to Key West

Origin Airport IATA Code
CHI
Destination Airport IATA Code
EYW
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Key West

Those who want guaranteed low prices for Chicago to Key West flights only need to visit Orbitz. We take advantage of the latest mobile technologies to make sure you get the best bargain on your trip and that everything goes smoothly and according to your plans.

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We will help you from booking to boarding on flights from Chicago to Key West. Whether you have questions about baggage limits, seat assignments or anything else, we will be there to answer them for you.

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We do not only get the best bargains on flights from Chicago to Key West, but we can tell you what to do once you get there. Whether it is a music festival, hotel recommendation or list of local attractions, Orbitz can help make your travel plan more exciting.

Combine Car Rental With Your Discount Flight For Even More Savings

Not only can we get bargain deals on flights from Chicago to Key West but we can book your transport as well. By combining car rental with Chicago to Key West flights, you can be sure to save money and start moving as soon as you hit the ground.

Use Orbitz On The Go To Stay Informed Using Your Smartphone

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Frequently asked questions

Am I able to catch a flight from Chicago to Key West now?
The Covid-19 Travel Advisor can answer all your queries about travel restrictions and quarantine when flying from Chicago to Key West.
Are there non-stop flights from Chicago to Key West?
Two carriers operate nonstop flights from Chicago, IL Airport (ORD-O’Hare Intl.) to Key West, FL Airport (EYW-Key West Intl.) — United Airlines and American Airlines. They’ll take you where you need to go in style and comfort.
What is the shortest flight from Chicago to Key West?
The shortest flight from Midway Intl. Airport (MDW) to EYW is around 3 hours and 32 minutes. Order a wine from the drink trolley, hone your travel itinerary or get to know your seat mate — you’ll have plenty of time on this medium-haul trip.
What airlines fly from Chicago to Key West most frequently?
There are a few airlines offering frequent flights from O’Hare Airport to Key West, FL Airport (EYW-Key West Intl.), including United Airlines (UA). A top pick for many travelers, it operates 60 flights on this route each month. Alternatively, book your favorite aisle (or window) seat with American Airlines (AA). You’ll have 52 monthly flights between Chicago and Key West to choose from with this carrier.
If I am not able to travel due to COVID-19, can I cancel my flight to Key West?
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 Key West 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 Key West with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Key West 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!

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.