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$79+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Clearwater are usually found in September or July, booked 62 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 June 12, 2025.

Round-trip from

$151
(Frontier)

One-way from

$79
(Southwest)

Popular in

February

Cheapest in

September

Average price

$259
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. 21% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Priceline deal was found by Cheapflights users on 6/11. 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.
Mon 9/156:21 amMDW - TPA
Nonstop2h 39mFrontier
Mon 9/2210:55 amTPA - MDW
Nonstop2h 49mFrontier
Deal found 6/11$128
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/78:05 pmMDW - TPA
Nonstop2h 35mSouthwest
Mon 8/116:55 amTPA - MDW
Nonstop2h 40mSouthwest
Deal found 6/10$157
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/124:22 pmMDW - TPA
1 stop5h 57mDelta
Tue 7/227:50 amTPA - MDW
1 stop5h 08mDelta
Deal found 6/11$197

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 June 12, 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

Tue 8/12

11:39 am-11:05 pm

1 stop10h 26m

Tampa

Thu 8/14

8:32 pm-10:24 pm

Nonstop2h 52m

$151

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 8/7

8:05 pm-11:40 pm

Nonstop2h 35m

Tampa

Mon 8/11

6:55 am-8:35 am

Nonstop2h 40m

$157

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 7/19

4:22 pm-11:19 pm

1 stop5h 57m

Tampa

Sat 7/26

5:20 am-9:45 am

1 stop5h 25m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 8/6

10:35 am-2:05 pm

Nonstop2h 30m

$79

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 8/29

9:10 am-3:23 pm

1 stop5h 13m

$103

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 7/25

6:47 pm-1:13 am

1 stop5h 26m

$119

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 7/4

10:31 am-8:21 am

2 stops20h 50m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 9, 2025.

The best time to book flights from Chicago Midway Airport to Clearwater is 62 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 June 12, 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 June 8, 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.

Weekly flight availability from Chicago Midway Airport to Clearwater

Explore weekly flight availability from Midway to Clearwater. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2025.

The most flights from MDW to CL9 are scheduled on a Monday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Clearwater by month

Plan your trip to Clearwater by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Clearwater ranges from 1.6 - 7.8 inches per month. August is typically the wettest month, when rainfall can reach 7.8 in. November is typically the driest time to visit Clearwater when rainfall is around 1.6 in.

Temperature in Clearwater by month

Plan your trip to Clearwater by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Clearwater, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 June 12, 2025.
See what other customers who have flown with Southwest, Delta and Frontier from Chicago to Clearwater have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

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
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

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
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Clearwater one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $79. Frontier flights start at $103 while deals on Delta start at $119 one-way.

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

    While on average a flight from Chicago Midway Airport to Clearwater is generally $258, our data shows the cheapest flight currently is $47. When looking at the most popular route, (Chicago Midway - Tampa), you can expect to pay $145 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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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$70Average$197FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$93Average$179FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$181Average$388FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$380FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$389FlexibilityNo cancel feeOn-time69%

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