$268 Cheap flights from Midway Intl. to Key West Intl. (MDW to EYW)

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Find The Best Dates To Fly from Midway Intl. to Key West Intl.

Compare Flight Prices from Chicago to Key West

Affordable Airfare Tickets from MDW to EYW Airport

The cheapest flights to Key West Intl. found within the past 7 days were $269 round trip and $268 one way. Prices and availability subject to change. Additional terms may apply.

Tue, Oct 7 - Tue, Oct 14
MDW
Chicago
EYW
Key West
$269 Roundtrip, found 1 day ago
$269
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 7 from Chicago to Key West, returning Tue, Oct 14, priced at $269 found 1 day ago
Wed, Nov 19 - Wed, Nov 26
MDW
Chicago
EYW
Key West
$269 Roundtrip, found 1 day ago
$269
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Nov 19 from Chicago to Key West, returning Wed, Nov 26, priced at $269 found 1 day ago
Tue, Aug 26 - Wed, Sep 3
MDW
Chicago
EYW
Key West
$273 Roundtrip, found 4 days ago
$273
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 26 from Chicago to Key West, returning Wed, Sep 3, priced at $273 found 4 days ago
Fri, Aug 15 - Tue, Aug 19
MDW
Chicago
EYW
Key West
$289 Roundtrip, found 22 hours ago
$289
Roundtrip
found 22 hours ago
Select Delta flight, departing Fri, Aug 15 from Chicago to Key West, returning Tue, Aug 19, priced at $289 found 22 hours ago
Thu, Aug 14 - Tue, Aug 19
MDW
Chicago
EYW
Key West
$294 Roundtrip, found 22 hours ago
$294
Roundtrip
found 22 hours ago
Select Delta flight, departing Thu, Aug 14 from Chicago to Key West, returning Tue, Aug 19, priced at $294 found 22 hours ago
Wed, Aug 13 - Tue, Aug 19
MDW
Chicago
EYW
Key West
$295 Roundtrip, found 22 hours ago
$295
Roundtrip
found 22 hours ago
Select Delta flight, departing Wed, Aug 13 from Chicago to Key West, returning Tue, Aug 19, priced at $295 found 22 hours ago
Fri, Aug 15 - Mon, Aug 25
MDW
Chicago
EYW
Key West
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Aug 15 from Chicago to Key West, returning Mon, Aug 25, priced at $309 found 2 days ago
Sun, Nov 9 - Sat, Nov 15
MDW
Chicago
EYW
Key West
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Nov 9 from Chicago to Key West, returning Sat, Nov 15, priced at $309 found 1 day ago
Wed, Aug 13 - Mon, Aug 25
MDW
Chicago
EYW
Key West
$314 Roundtrip, found 2 days ago
$314
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Aug 13 from Chicago to Key West, returning Mon, Aug 25, priced at $314 found 2 days ago
Tue, Aug 26 - Sat, Aug 30
MDW
Chicago
EYW
Key West
$316 Roundtrip, found 4 days ago
$316
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 26 from Chicago to Key West, returning Sat, Aug 30, priced at $316 found 4 days ago

Key West Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3 out of 5
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Commodore s Compound by Brightwild Huge Home

Commodore s Compound by Brightwild Huge Home

2 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
per person
Aug 29 - Sep 1
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
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Flight information from Chicago to Key West

 

Traveling From
Midway Intl.
Traveling To
Key West Intl.
Shortest Flight Time
 hours mins
Earliest Departure Time
Latest Departure Time
Lowest Flight Price
$269

Route Info

Flight path for flights from Chicago Midway International Airport to Key West International Airport.


Origin:
MDW - Chicago Midway International Airport
Destination:
EYW - Key West International Airport
Distance:
1,245.00 miles


Discover our best flights from Chicago MDW to Key West EYW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Chicago MDW to Key West EYW at the right price  

Airfares to Key West EYW from Chicago MDW currently cost between $269 and $354. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Chicago MDW to Key West EYW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Chicago MDW to Key West EYW on Travelocity starting at $268. Prices and availability subject to change. Additional terms may apply. 

 

Get to Key West EYW from Chicago MDW quicker with direct flights. 

Get to Key West faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to EYW from MDW to take around hour(s) min(s).  

 

Find our cheapest airfares for flights from Chicago MDW to Key West EYW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to EYW from MDW. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Chicago MDW to Key West EYW today 

If you’re flexible about when you travel, October is usually the cheapest month to fly from Chicago MDW to Key West EYW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Key West EYW from Chicago MDW 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to EYW from MDW have this option.  

 

Travel with confidence when you book flights to Key West EYW from Chicago MDW with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.