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$69+ Cheap flights from Clearwater, FL to Midway (MDW)

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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Clearwater to Chicago Midway are usually found in January or December, booked 87 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Clearwater to Midway

Keep the following information in mind while searching for Clearwater to Midway flight deals. Data was last updated July 31, 2025.

Round-trip from

$117
(Priceline)

One-way from

$71
(Frontier)

Popular in

June

Cheapest in

January

Average price

$255
From Clearwater to Chicago Midway
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One-way flight from Clearwater to Chicago Midway
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Highest demand for flights based on searches. 13% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Clearwater to Midway

Cheapest flights from Clearwater to Midway
Explore the most affordable flight options available from Clearwater to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Priceline deal was found by Cheapflights users on 7/30. 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.
Fri 9/1210:55 amTPA - MDW
Nonstop2h 49mFrontier
Fri 9/196:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 7/30$117
This Southwest deal was found by Cheapflights users on 7/31. 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.
Sat 8/307:20 amTPA - MDW
Nonstop2h 40mSouthwest
Sat 9/65:30 pmMDW - TPA
Nonstop2h 35mSouthwest
Deal found 7/31$157
This Delta deal was found by Cheapflights users on 7/31. 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.
Thu 10/231:59 pmTPA - MDW
1 stop5h 26mDelta
Tue 10/286:00 amMDW - TPA
1 stop5h 36mDelta
Deal found 7/31$197

Cheapflights Fare Finder

 
Customize your flight search to find flights from Clearwater to Midway 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 July 31, 2025.
Use the filters below to find and compare flights from Clearwater to Chicago Midway Airport that are best for you.

Fly from

Clearwater

Fly to

Midway

Route

Depart

Return

Price

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 9/12

10:55 am-12:44 pm

Nonstop2h 49m

Chicago Midway

Fri 9/19

6:21 am-9:57 am

Nonstop2h 36m

$117

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 8/30

7:20 am-9:00 am

Nonstop2h 40m

Chicago Midway

Sat 9/6

5:30 pm-9:05 pm

Nonstop2h 35m

$157

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 10/23

1:59 pm-6:25 pm

1 stop5h 26m

Chicago Midway

Tue 10/28

6:00 am-12:36 pm

1 stop5h 36m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sun 10/5

10:55 am-12:44 pm

Nonstop2h 49m

$69

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 8/30

7:20 am-9:00 am

Nonstop2h 40m

$79

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 8/30

6:21 am-12:28 pm

1 stop7h 07m

$99

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 9/11

10:26 pm-4:43 pm

2 stops19h 17m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Best time to book a flight from Clearwater to Midway

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

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

Use this chart to determine the optimal time to book a round-trip flight from Clearwater to Midway. Price data was last updated on July 25, 2025.

To ensure you get the cheapest price possible for a flight from Clearwater to Chicago Midway Airport, you should look to book at least 87 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, April is the cheapest month in which you can book a flight from Clearwater to Chicago Midway Airport (average of $160). Flying from Clearwater to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 CL9 to MDW?

Find hourly flight availability from Clearwater to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

When flying from Clearwater to Chicago Midway Airport, 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 Clearwater to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Clearwater to Midway. Price data was last updated on July 27, 2025.

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

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Frontier from Clearwater to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

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

    One-way options have recently been found by users for as low as $71 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $99 one-way.

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

    Looking at all options, your cheapest flight can be booked for $68. While the most popular route (Tampa - Chicago Midway) can be booked for $109 on average our data indicates $203 when flying from Clearwater to Chicago Midway Airport.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Clearwater to Chicago Midway Airport (average of $160). Flying from Clearwater to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Top 4 airlines flying from Clearwater to Midway

Discover the top 4 airlines that operate flights from Clearwater to Midway. 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$76Average$165FlexibilityNo cancel feeOn-time65%
FrontierCheapest$80Average$170FlexibilityNo cancel feeOn-time62%
DeltaCheapest$114Average$296FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$162Average$341FlexibilityNo cancel feeOn-time63%

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