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$52+ 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 Sunday and return on a Friday

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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/145:57 pmMDW - TPA
Nonstop2h 35mFrontier
Mon 11/1710:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 10/29$106
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Wed 12/246:12 amMDW - TPA
1 stop17h 14mFrontier
Wed 12/315:45 amTPA - MDW
1 stop17h 27mFrontier
Deal found 10/28$108
This Priceline deal was found by Cheapflights users on 10/29. 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.
Thu 11/139:15 amMDW - TPA
1 stop8h 27mFrontier
Wed 11/198:25 amTPA - MDW
1 stop5h 16mFrontier
Deal found 10/29$110
This Frontier deal was found by Cheapflights users on 10/29. 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.
Thu 11/139:15 amMDW - TPA
1 stop8h 27mFrontier
Sat 11/158:30 amTPA - MDW
1 stop11h 09mFrontier
Deal found 10/29$111
This Priceline deal was found by Cheapflights users on 10/29. 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.
Thu 11/136:30 amMDW - TPA
1 stop7h 12mFrontier
Mon 11/1710:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 10/29$112
This Priceline deal was found by Cheapflights users on 10/28. 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.
Mon 11/106:30 amMDW - TPA
1 stop7h 14mFrontier
Mon 11/1710:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 10/28$117
This Frontier deal was found by Cheapflights users on 10/29. 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.
Fri 11/145:57 pmMDW - TPA
Nonstop2h 35mFrontier
Sat 11/158:30 amTPA - MDW
1 stop11h 09mFrontier
Deal found 10/29$123
This Frontier deal was found by Cheapflights users on 10/28. 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.
Thu 11/136:30 amMDW - TPA
1 stop7h 12mFrontier
Sun 11/1610:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 10/28$125

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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$106
(Kiwi.com)

One-way from

$52
(Trip.com)

Popular in

February

Cheapest in

September

Average price

$183
Provider with most accurate pricing for Chicago (CHI)-Tampa flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Tampa flights.
Search Deals
From Chicago Midway to Clearwater
Search Deals
One-way flight from Chicago Midway to Clearwater
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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

Sat 2/7

12:00 pm-8:45 pm

1 stop7h 45m

Tampa

Sat 2/14

6:50 am-8:35 am

Nonstop2h 45m

$187

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/3

6:00 am-1:42 pm

1 stop6h 42m

Tampa

Wed 3/4

6:15 am-12:35 pm

1 stop7h 20m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 12/2

9:34 am-4:36 pm

1 stop6h 02m

Tampa

Sat 12/6

5:30 am-9:54 am

1 stop5h 24m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 1/23

5:40 pm-9:15 pm

Nonstop2h 35m

Tampa

Thu 1/29

4:45 pm-6:35 pm

Nonstop2h 50m

$202

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 11/27

10:47 am-6:29 pm

1 stop6h 42m

Tampa

Thu 12/4

5:45 am-12:34 pm

1 stop7h 49m

$207

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 1/14

1:25 pm-5:00 pm

Nonstop2h 35m

Tampa

Wed 3/4

7:15 am-9:05 am

Nonstop2h 50m

$212

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 11/11

9:34 am-3:20 pm

1 stop4h 46m

Tampa

Tue 12/9

12:53 pm-4:34 pm

1 stop4h 41m

$223

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 1/8

10:15 am-5:45 pm

2 stops6h 30m

Tampa

Sun 1/11

6:40 am-8:25 am

Nonstop2h 45m

$227

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 1/24

9:45 am-8:05 pm

2 stops9h 20m

Tampa

Wed 1/28

12:50 pm-7:00 pm

1 stop7h 10m

$227

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 1/5

5:20 am-8:55 am

Nonstop2h 35m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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 October 24, 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Clearwater (average of $56). Flying from Chicago Midway Airport to Clearwater in June is currently the most expensive (average of $167). 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 October 30, 2025.

When flying from Chicago Midway Airport to Clearwater, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 14% versus a flight in the evening.

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 October 26, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Clearwater flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Saturday 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 October 30, 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
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
7.9
Good
7,993 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
8,115 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
3,123 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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 6h 42m. Airlines will cover a distance of 998 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    While on average a flight from Chicago Midway Airport to Clearwater is generally $190, our data shows the cheapest flight currently is $54. When looking at the most popular route, (Chicago Midway - Tampa), you can expect to pay $110 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Clearwater (average of $56). Flying from Chicago Midway Airport to Clearwater in June is currently the most expensive (average of $167). 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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Top 4 airlines flying from Midway to Clearwater

Discover the top 4 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$212FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$180FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$177Average$385FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$385FlexibilityNo cancel feeOn-timeN/A

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