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$377+ Cheap flights from Toledo, OH to Key West (TOL - EYW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
TOL — EYW
Mar 12 — Mar 191
Thu 3/12
Thu 3/19
1 adult, Economy
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Cheap flight deals from Toledo to Key West

Cheapest flights from Toledo to Key West
Explore the most affordable flight options available from Toledo to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/229:24 am
TOL
-
EYW
1 stop4h 55m
Allegiant Air
Thu 2/264:13 pm
EYW
-
TOL
1 stop22h 42m
Allegiant Air
Deal found 2/7$377
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2111:34 am
TOL
-
EYW
1 stop26h 45m
Allegiant Air
Wed 2/2512:38 pm
EYW
-
TOL
1 stop19h 55m
Allegiant Air
Deal found 2/6$415
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/49:15 pm
TOL
-
EYW
1 stop11h 51m
Multiple Airlines
Sat 4/1111:54 am
EYW
-
TOL
1 stop20h 55m
Multiple Airlines
Deal found 2/9$460
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/49:15 pm
TOL
-
EYW
1 stop17h 37m
Allegiant Air
Sun 4/123:50 pm
EYW
-
TOL
1 stop23h 02m
Allegiant Air
Deal found 2/8$461
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:18 am
TOL
-
EYW
1 stop12h 24m
Allegiant Air
Wed 4/812:39 pm
EYW
-
TOL
1 stop20h 20m
Allegiant Air
Deal found 2/6$464
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:18 am
TOL
-
EYW
1 stop12h 24m
Allegiant Air
Mon 4/1311:01 am
EYW
-
TOL
2 stops51h 36m
Allegiant Air
Deal found 2/6$467
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/159:18 am
TOL
-
EYW
1 stop12h 25m
Allegiant Air
Sun 3/2210:27 pm
EYW
-
TOL
1 stop19h 22m
Allegiant Air
Deal found 2/6$479
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:18 am
TOL
-
EYW
1 stop12h 24m
Multiple Airlines
Wed 4/812:25 pm
EYW
-
TOL
2 stops20h 34m
Multiple Airlines
Deal found 2/6$490
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:18 am
TOL
-
EYW
1 stop12h 24m
Allegiant Air
Sun 4/123:50 pm
EYW
-
TOL
1 stop23h 02m
Allegiant Air
Deal found 2/6$506

Find flight deals from Toledo to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Toledo (TOL) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$377
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$494
Provider with most accurate pricing for Toledo Express-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toledo Express-Key West flights.
Search Deals
From Toledo Express to Key West
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toledo to Key West that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 10, 2026.
Use the filters below to find and compare flights from Toledo to Key West that are best for you.

Fly from

Toledo

Fly to

Key West

Route

Depart

Return

Price

ToledoKey West

TOL - EYW

TOLEYW

Toledo Express

Sun 2/22

9:24 am-2:19 pm

1 stop4h 55m

Key West

Thu 2/26

4:13 pm-2:55 pm

1 stop22h 42m

$377

ToledoKey West

TOL - EYW

TOLEYW

Toledo Express

Sat 2/21

11:34 am-2:19 pm

1 stop26h 45m

Key West

Wed 2/25

12:38 pm-8:33 am

1 stop19h 55m

$415

ToledoKey West

TOL - EYW

TOLEYW

Toledo Express

Sat 4/4

9:15 pm-9:06 am

1 stop11h 51m

Key West

Sat 4/11

11:54 am-8:49 am

1 stop20h 55m

$460

ToledoKey West

TOL - EYW

TOLEYW

Toledo Express

Sat 4/4

9:15 pm-2:52 pm

1 stop17h 37m

Key West

Sun 4/12

3:50 pm-2:52 pm

1 stop23h 02m

$461

ToledoKey West

TOL - EYW

TOLEYW

Toledo Express

Thu 4/2

9:18 am-9:42 pm

1 stop12h 24m

Key West

Wed 4/8

12:39 pm-8:59 am

1 stop20h 20m

$464

ToledoKey West

TOL - EYW

TOLEYW

Toledo Express

Thu 4/2

9:18 am-9:42 pm

1 stop12h 24m

Key West

Mon 4/13

11:01 am-2:37 pm

2 stops51h 36m

$467

ToledoKey West

TOL - EYW

TOLEYW

Toledo Express

Sun 3/15

9:18 am-9:43 pm

1 stop12h 25m

Key West

Sun 3/22

10:27 pm-5:49 pm

1 stop19h 22m

$479

ToledoKey West

TOL - EYW

TOLEYW

Toledo Express

Thu 4/2

9:18 am-9:42 pm

1 stop12h 24m

Key West

Wed 4/8

12:25 pm-8:59 am

2 stops20h 34m

$490

ToledoKey West

TOL - EYW

TOLEYW

Toledo Express

Thu 4/2

9:18 am-9:42 pm

1 stop12h 24m

Key West

Sun 4/12

12:25 pm-2:52 pm

2 stops26h 27m

$512

ToledoKey West

TOL - EYW

TOLEYW

Toledo Express

Thu 4/2

9:18 am-9:42 pm

1 stop12h 24m

Key West

Tue 4/7

12:25 pm-12:50 pm

2 stops24h 25m

$528

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Compare providers for flights from Toledo to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Toledo to Key West in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Toledo, Ohio-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toledo, Ohio-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toledo, Ohio-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toledo, Ohio-Key West flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toledo, Ohio-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Toledo to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Toledo with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Toledo to Key West

What is the cheapest month to book a flight from Toledo, Ohio to Key West?

Currently, March is the cheapest month in which you can book a flight from Toledo, Ohio to Key West (average of $165). Flying from Toledo, Ohio to Key West in October is currently the most expensive (average of $252). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Toledo to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Toledo, Ohio to Key West?

    Airlines like Allegiant Air fly from Toledo, Ohio to Key West in about 4h 55m. The time it takes to get you to your destination can typically vary by up to . Toledo, Ohio and Key West are separated by a distance of 1182 mi.

  • Can I find deals for flights from Toledo to Key West that include hotel bookings?

    Yes. In addition to deals on Toledo to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Toledo to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Toledo to Key West.

  • Can I find deals for business class flights from Toledo to Key West?

    Yes. Cheapflights offers flight deals from Toledo to Key West by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Toledo, Ohio to Key West?

    Currently, March is the cheapest month in which you can book a flight from Toledo, Ohio to Key West (average of $165). Flying from Toledo, Ohio to Key West in October is currently the most expensive (average of $252). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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