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Clearwater

$55+ Cheap flights from Midway (MDW) to Clearwater, FL

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
oct. 11 — oct. 181
sam. 10/11
sam. 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Clearwater are usually found in September or October, booked 48 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Midway to Clearwater

Keep the following information in mind while searching for Midway to Clearwater flight deals. Data was last updated septembre 11, 2025.

Round-trip from

$103
(Cheapflightsfares)

One-way from

$55
(Cheapflightsfares)

Popular in

February

Cheapest in

September

Average price

$158
From Chicago Midway to Clearwater
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One-way flight from Chicago Midway to Clearwater
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Highest demand for flights based on searches. 17% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Clearwater

Cheapest flights from Midway to Clearwater
Explore the most affordable flight options available from Midway to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septembre 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 10/56:21 amMDW - TPA
Nonstop2h 36mFrontier
dim. 10/129:57 amTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/10$103
This Frontier deal was found by Cheapflights users on 9/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/36:06 pmMDW - TPA
Nonstop2h 35mFrontier
lun. 11/1010:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/9$104
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/36:21 amMDW - TPA
Nonstop2h 36mFrontier
dim. 10/129:57 amTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/10$105
This Frontier deal was found by Cheapflights users on 9/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 11/77:50 amMDW - TPA
Nonstop2h 34mFrontier
dim. 11/910:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/9$106
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/317:50 amMDW - TPA
Nonstop2h 34mFrontier
dim. 11/210:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/9$107
This Frontier deal was found by Cheapflights users on 9/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/139:00 amMDW - TPA
Nonstop2h 37mFrontier
mar. 10/147:30 amTPA - MDW
1 stop7h 08mFrontier
Deal found 9/9$109
This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 10/125:20 amMDW - TPA
Nonstop2h 35mFrontier
dim. 10/129:57 amTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/11$110
This Trip.com deal was found by Cheapflights users on 9/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/209:45 amMDW - TPA
Nonstop2h 37mFrontier
ven. 10/242:22 pmTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/10$116
This Frontier deal was found by Cheapflights users on 9/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 10/56:21 amMDW - TPA
Nonstop2h 36mFrontier
dim. 10/510:27 pmTPA - MDW
1 stop9h 44mFrontier
Deal found 9/11$117
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 9/286:21 amMDW - TPA
Nonstop2h 36mFrontier
dim. 10/510:55 amTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/10$122
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/24:56 pmMDW - TPA
1 stop5h 43mFrontier
dim. 10/510:55 amTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/10$123
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/2312:30 pmMDW - TPA
1 stop7h 04mFrontier
lun. 10/272:22 pmTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/10$124

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Clearwater 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 septembre 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Clearwater that are best for you.

Fly from

Midway

Fly to

Clearwater

Route

Depart

Return

Price

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

dim. 10/12

5:20 am-8:55 am

Nonstop2h 35m

Tampa

dim. 10/12

9:57 am-11:44 am

Nonstop2h 47m

$110

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

lun. 10/13

9:00 am-12:37 pm

Nonstop2h 37m

Tampa

lun. 10/13

7:16 pm-11:46 pm

1 stop5h 30m

$148

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mar. 11/4

9:05 am-12:40 pm

Nonstop2h 35m

Tampa

mar. 11/4

4:30 pm-6:15 pm

Nonstop2h 45m

$157

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mer. 10/15

8:05 am-7:32 pm

1 stop10h 27m

Tampa

lun. 10/20

2:22 pm-4:09 pm

Nonstop2h 47m

$159

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

ven. 10/10

9:00 am-3:53 pm

1 stop5h 53m

Tampa

lun. 10/13

1:37 pm-3:24 pm

Nonstop2h 47m

$160

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mer. 9/17

9:00 am-8:06 pm

1 stop10h 06m

Tampa

dim. 9/21

10:27 pm-7:11 am

1 stop9h 44m

$167

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

sam. 12/6

9:45 am-3:00 pm

1 stop4h 15m

Tampa

sam. 12/6

4:55 pm-6:40 pm

Nonstop2h 45m

$174

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

sam. 10/4

9:55 am-3:40 pm

1 stop4h 45m

Tampa

mer. 10/8

6:55 am-8:35 am

Nonstop2h 40m

$176

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

sam. 9/27

6:40 am-10:10 am

Nonstop2h 30m

Tampa

sam. 10/4

7:05 am-8:45 am

Nonstop2h 40m

$181

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

ven. 10/31

7:50 am-11:24 am

Nonstop2h 34m

$57

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 19 results
1
2

Best time to book a flight from Midway to Clearwater

Have a flexible travel schedule? Discover the best time to fly to Clearwater from Midway 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 Chicago Midway Airport to Clearwater

How far ahead should I book a flight from Chicago Midway Airport to Clearwater?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Clearwater. Price data was last updated on August 29, 2025.

The best time to book flights from Chicago Midway Airport to Clearwater is 48 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago Midway Airport to Clearwater?

Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Clearwater (average of $206). Flying from Chicago Midway Airport to Clearwater in November is currently the most expensive (average of $289). 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.

What is the cheapest time of day to fly from MDW to CL9?

Find hourly flight availability from Midway to Clearwater. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septembre 11, 2025.

When flying from Chicago Midway Airport to Clearwater, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago Midway Airport to Clearwater?

Use this chart to determine the cheapest time to fly round-trip from Midway to Clearwater. Price data was last updated on September 7, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Clearwater flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Clearwater

Get insights into the airlines that provide service to Clearwater. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Clearwater. Reviews last updated septembre 11, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Clearwater, such as Southwest, Delta, and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Midway to Clearwater. 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 Chicago Midway Airport to Clearwater?

    Departing from Chicago Midway Airport to Clearwater will take you 2h 35m. Airlines will cover a distance of 998 mi. Generally, flights for this route are nonstop.

  • What are the cheapest flights from Chicago Midway Airport to Clearwater?

    While on average a flight from Chicago Midway Airport to Clearwater is generally $193, our data shows the cheapest flight currently is $43. When looking at the most popular route, (Chicago Midway - Tampa), you can expect to pay $104 for that flight.

  • Can I find deals for flights from Midway to Clearwater that include hotel bookings?

    Yes. In addition to deals on Midway to Clearwater flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Clearwater?

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

  • Can I find deals for business class flights from Midway to Clearwater?

    Yes. Cheapflights offers flight deals from Midway to Clearwater 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 Chicago Midway Airport to Clearwater?

    Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Clearwater (average of $206). Flying from Chicago Midway Airport to Clearwater in November is currently the most expensive (average of $289). 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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Alternative routes for Midway to Clearwater

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Midway to Clearwater

Discover the top 5 airlines that operate flights from Midway to Clearwater. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$215FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$180FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$176Average$382FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$349FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$259Average$364FlexibilityNo cancel feeOn-time69%

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