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$63+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Apr 10 — Apr 171
Fri 4/10
Fri 4/17
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 22 days in advance, depart on a Thursday or Friday and return on a Friday

Cheap 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 March 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Tue 4/142:15 pm
MDW
-
TPA
1 stop9h 11m
Frontier
Tue 4/218:44 am
TPA
-
MDW
1 stop11h 47m
Frontier
Deal found 3/6$123
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 4/166:00 am
MDW
-
TPA
1 stop17h 26m
Frontier
Mon 4/207:50 pm
TPA
-
MDW
1 stop24h 41m
Frontier
Deal found 3/6$124
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Wed 4/292:15 pm
MDW
-
TPA
1 stop9h 11m
Frontier
Mon 5/47:50 pm
TPA
-
MDW
1 stop27h 29m
Frontier
Deal found 3/9$126
This eDestinos deal was found by Cheapflights users on 3/9. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:15 pm
MDW
-
TPA
1 stop9h 11m
Frontier
Wed 4/158:44 am
TPA
-
MDW
1 stop11h 47m
Frontier
Deal found 3/9$133
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:15 pm
MDW
-
TPA
1 stop9h 11m
Frontier
Tue 5/55:04 pm
TPA
-
MDW
1 stop5h 58m
Frontier
Deal found 3/10$138
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Wed 4/152:15 pm
MDW
-
TPA
1 stop9h 11m
Frontier
Fri 4/247:02 am
TPA
-
MDW
1 stop13h 29m
Frontier
Deal found 3/6$139
This Kiwi.com deal was found by Cheapflights users on 3/8. 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.
Wed 4/152:15 pm
MDW
-
TPA
1 stop9h 11m
Multiple Airlines
Tue 4/216:02 pm
TPA
-
MDW
1 stop5h 12m
Multiple Airlines
Deal found 3/8$140
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:56 pm
MDW
-
TPA
1 stop8h 30m
Frontier
Wed 4/228:44 am
TPA
-
MDW
1 stop11h 47m
Frontier
Deal found 3/10$145
This Southwest deal was found by Cheapflights users on 3/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/255:55 pm
MDW
-
TPA
Nonstop2h 35m
Southwest
Sat 5/26:55 am
TPA
-
MDW
Nonstop2h 45m
Southwest
Deal found 3/8$147
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Mon 4/202:15 pm
MDW
-
TPA
1 stop9h 11m
Multiple Airlines
Mon 4/276:02 pm
TPA
-
MDW
1 stop5h 17m
Multiple Airlines
Deal found 3/6$148
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 4/257:34 pm
MDW
-
TPA
1 stop11h 00m
Multiple Airlines
Mon 4/276:02 pm
TPA
-
MDW
1 stop5h 17m
Multiple Airlines
Deal found 3/6$149
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Tue 4/142:15 pm
MDW
-
TPA
1 stop9h 11m
Multiple Airlines
Tue 4/216:02 pm
TPA
-
MDW
1 stop5h 12m
Multiple Airlines
Deal found 3/6$150

Find flight deals from Midway to Clearwater

Keep the following information in mind while searching for Midway to Clearwater flight deals. Data was last updated March 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$123
(Kiwi.com)

One-way from

$63
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$357
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. 1% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Clearwater that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 4/14

5:55 am-9:25 am

Nonstop2h 30m

Tampa

Wed 4/15

7:15 am-9:05 am

Nonstop2h 50m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 5/8

8:30 pm-12:05 am

Nonstop2h 35m

Tampa

Sat 5/16

6:55 am-8:40 am

Nonstop2h 45m

$217

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 4/20

8:30 pm-12:05 am

Nonstop2h 35m

Tampa

Mon 4/27

3:30 pm-8:50 pm

1 stop6h 20m

$227

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 5/19

12:50 pm-4:25 pm

Nonstop2h 35m

Tampa

Sat 5/23

6:55 am-8:40 am

Nonstop2h 45m

$243

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sun 4/12

5:00 am-8:30 am

Nonstop2h 30m

Tampa

Thu 4/16

4:20 pm-6:10 pm

Nonstop2h 50m

$257

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 5/9

5:55 pm-9:30 pm

Nonstop2h 35m

Tampa

Sun 5/10

7:00 am-8:50 am

Nonstop2h 50m

$257

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 4/3

6:30 pm-10:05 pm

Nonstop2h 35m

Tampa

Wed 4/8

6:10 am-11:35 am

1 stop6h 25m

$267

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/24

3:35 pm-8:50 pm

1 stop4h 15m

Tampa

Tue 3/31

7:00 am-8:50 am

Nonstop2h 50m

$283

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sun 4/5

12:30 pm-5:35 pm

1 stop4h 05m

Tampa

Wed 4/8

2:35 pm-8:05 pm

1 stop6h 30m

$297

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/24

4:45 pm-10:00 pm

1 stop4h 15m

Tampa

Mon 3/30

8:20 pm-12:05 am

1 stop4h 45m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

Showing 1-10 of 24 resultsSorted by cheapest first
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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 March 6, 2026.

The best time to book flights from Chicago Midway Airport to Clearwater is 22 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 $165). 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 March 11, 2026.

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 February 21, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Clearwater flight should consider departing on Tuesday evenings when fares are most often at their lowest. Tuesday mornings 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 March 11, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Clearwater, such as Southwest and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,317 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
8.0
Very good
4,317 reviews
Southwest
8.0
Very good
4,317 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Frontier
5.7
Fair
3,033 reviews
Southwest
8.0
Very good
4,317 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 30m. Airlines will cover a distance of 998 mi. Generally, flights for this route are nonstop.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $43. Southwest flights start at $88 while deals on Delta start at $98 one-way.

  • What are the most reliable airlines from Chicago Midway Airport to Clearwater?

    Consider Frontier (84%), Southwest (72%) or Volaris (47%) when booking your flight. These represent the most reliable airlines when flying from Chicago Midway Airport to Clearwater.

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

    While on average a flight from Chicago Midway Airport to Clearwater is generally $221, our data shows the cheapest flight currently is $49. When looking at the most popular route, (Chicago Midway - Tampa), you can expect to pay $155 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 $165). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Midway to Clearwater

Discover the top 3 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 March 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$70Average$180FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$529FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$168Average$370FlexibilityNo cancel feeOn-time63%

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