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$109+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
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 14 days in advance, depart on a Friday or Wednesday 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 August 1, 2026.

This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/411:50 am
MDW
-
TPA
1 stop5h 59m
Frontier
Tue 9/82:25 pm
TPA
-
MDW
1 stop9h 22m
Frontier
Deal found 7/31$208
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:55 pm
MDW
-
TPA
Nonstop2h 30m
Southwest
Mon 8/245:15 am
TPA
-
MDW
Nonstop2h 40m
Southwest
Deal found 7/30$209
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:25 am
MDW
-
TPA
1 stop10h 00m
Frontier
Sat 10/32:03 pm
TPA
-
MDW
1 stop4h 48m
Frontier
Deal found 7/30$210
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:05 am
MDW
-
TPA
1 stop11h 44m
Frontier
Sun 8/302:25 pm
TPA
-
MDW
1 stop9h 22m
Frontier
Deal found 7/31$211
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
MDW
-
TPA
2 stops7h 05m
Southwest
Wed 9/97:35 am
TPA
-
MDW
Nonstop2h 40m
Southwest
Deal found 7/29$212
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:50 pm
MDW
-
TPA
1 stop5h 55m
Southwest
Mon 9/215:15 am
TPA
-
MDW
Nonstop2h 40m
Southwest
Deal found 7/30$213
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:55 pm
MDW
-
TPA
Nonstop2h 35m
Southwest
Sun 9/68:10 am
TPA
-
MDW
Nonstop2h 40m
Southwest
Deal found 7/29$214
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:30 am
MDW
-
TPA
Nonstop2h 30m
Southwest
Tue 9/811:35 am
TPA
-
MDW
Nonstop2h 40m
Southwest
Deal found 7/30$216
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/166:00 am
MDW
-
TPA
1 stop6h 15m
Delta
Wed 1/62:00 pm
TPA
-
MDW
1 stop5h 37m
Delta
Deal found 7/28$217
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:25 am
MDW
-
TPA
1 stop10h 00m
Frontier
Mon 9/216:00 pm
TPA
-
MDW
1 stop6h 44m
Frontier
Deal found 7/31$218
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:55 pm
MDW
-
TPA
Nonstop2h 30m
Southwest
Sat 8/222:50 pm
TPA
-
MDW
1 stop5h 30m
Southwest
Deal found 7/30$219

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 August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$208
(Trip.com)

One-way from

$109
(Delta)

Popular in

June

Cheapest in

September

Average price

$230
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. 14% potential increase in price ($48 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 August 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 August 1, 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

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 9/3

3:15 pm-6:50 pm

Nonstop2h 35m

Tampa

Sun 9/6

8:10 am-9:50 am

Nonstop2h 40m

$214

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 9/10

12:20 pm-5:10 pm

1 stop3h 50m

Tampa

Sat 9/12

7:25 am-9:05 am

Nonstop2h 40m

$215

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 8/25

7:40 am-2:50 pm

2 stops6h 10m

Tampa

Tue 9/1

8:05 am-1:30 pm

1 stop6h 25m

$222
Quickest round-trip

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 8/27

7:55 pm-11:25 pm

Nonstop2h 30m

Tampa

Thu 9/3

5:15 am-6:55 am

Nonstop2h 40m

$222

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 9/9

6:05 am-2:02 pm

1 stop6h 57m

Tampa

Mon 9/14

6:48 pm-10:44 pm

1 stop4h 56m

$223

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 10/1

7:05 am-12:00 pm

1 stop3h 55m

Tampa

Sat 10/3

8:50 am-3:25 pm

1 stop7h 35m

$224

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 9/11

7:55 pm-11:30 pm

Nonstop2h 35m

Tampa

Mon 9/14

6:55 am-11:30 am

1 stop5h 35m

$224

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 8/27

3:15 pm-6:50 pm

Nonstop2h 35m

Tampa

Mon 8/31

5:25 pm-7:00 pm

Nonstop2h 35m

$235

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 9/14

6:20 pm-10:00 pm

Nonstop2h 40m

Tampa

Mon 9/21

5:15 am-6:55 am

Nonstop2h 40m

$235

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 9/4

6:20 pm-10:00 pm

Nonstop2h 40m

Tampa

Sun 9/6

8:10 am-9:50 am

Nonstop2h 40m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 23 resultsSorted by cheapest first
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2
3

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

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 August 1, 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 18% versus a flight in the evening.

How much does it cost to fly round-trip from Chicago Midway Airport to Clearwater?

Airfare is typical for this route at the moment.
Chicago Midway Airport to Clearwater flights typically cost between $158 and $391 in September.
The cheapest round-trip price found within the last 5 days was $208 on Frontier (Sep 4-Sep 8).

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 August 1, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Clearwater flight should consider departing on Monday at noon when fares are most often at their lowest. Monday 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 August 1, 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
4,230 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

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
4,230 reviews
Southwest
8.0
Very good
4,230 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

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
5.6
Fair
2,740 reviews
Southwest
8.0
Very good
4,230 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

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 35m. 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 $50. Southwest flights start at $89 while deals on Delta start at $98 one-way.

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

    Consider Southwest (62%), Frontier (0%) or Volaris (0%) 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 $329, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Chicago Midway - Tampa), you can expect to pay $169 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.

See more FAQs

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Top 2 airlines flying from Midway to Clearwater

Discover the top 2 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 August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$66Average$184FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$190Average$400FlexibilityNo cancel feeOn-time63%

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