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Clearwater

$69+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
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 Thursday 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 diciembre 12, 2025.

This Southwest deal was found by Cheapflights users on 12/10. 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.
mié. 12/241:30 pmMDW - TPA
1 stop5h 25mSouthwest
jue. 12/257:15 amTPA - MDW
Nonstop2h 45mSouthwest
Deal found 12/10$202
This CheapOair deal was found by Cheapflights users on 12/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/1512:18 pmMDW - TPA
1 stop15h 07mFrontier
vie. 1/25:45 amTPA - MDW
1 stop8h 36mFrontier
Deal found 12/8$209
This Frontier deal was found by Cheapflights users on 12/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/296:12 amMDW - TPA
1 stop11h 38mFrontier
jue. 1/85:35 amTPA - MDW
1 stop6h 56mFrontier
Deal found 12/9$210
This Southwest deal was found by Cheapflights users on 12/10. 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.
mié. 12/241:30 pmMDW - TPA
1 stop5h 25mSouthwest
mié. 12/314:15 pmTPA - MDW
1 stop4h 20mSouthwest
Deal found 12/10$212
This Frontier deal was found by Cheapflights users on 12/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/2410:21 amMDW - TPA
1 stop9h 19mFrontier
mar. 12/306:45 amTPA - MDW
1 stop14h 10mFrontier
Deal found 12/10$213
This Booking.com deal was found by Cheapflights users on 12/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/232:01 pmMDW - TPA
1 stop14h 30mFrontier
mar. 1/135:15 amTPA - MDW
1 stop6h 19mFrontier
Deal found 12/8$223
This Frontier deal was found by Cheapflights users on 12/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/3110:21 amMDW - TPA
1 stop9h 19mFrontier
jue. 1/85:35 amTPA - MDW
1 stop6h 56mFrontier
Deal found 12/9$225
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/186:33 pmMDW - TPA
1 stop4h 53mFrontier
dom. 12/216:45 amTPA - MDW
1 stop16h 05mFrontier
Deal found 12/10$238
This Frontier deal was found by Cheapflights users on 12/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/172:49 pmMDW - TPA
1 stop7h 40mFrontier
sáb. 12/205:55 amTPA - MDW
1 stop8h 26mFrontier
Deal found 12/9$240
This Southwest deal was found by Cheapflights users on 12/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/162:55 pmMDW - TPA
Nonstop2h 35mSouthwest
mié. 12/247:15 pmTPA - MDW
Nonstop2h 45mSouthwest
Deal found 12/9$242

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 diciembre 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$108
(Trip.com)

One-way from

$69
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$560
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. 16% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 diciembre 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

mar. 1/13

10:10 am-1:50 pm

Nonstop2h 40m

Tampa

mar. 1/20

7:15 am-9:05 am

Nonstop2h 50m

$167

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

sáb. 2/7

2:30 pm-6:05 pm

Nonstop2h 35m

Tampa

sáb. 2/14

6:50 am-8:35 am

Nonstop2h 45m

$168

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mié. 1/7

6:00 am-12:05 pm

1 stop5h 05m

Tampa

mié. 1/7

4:25 pm-10:55 pm

2 stops7h 30m

$182

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

jue. 1/1

1:30 pm-7:55 pm

1 stop5h 25m

Tampa

mar. 1/6

10:25 am-4:35 pm

2 stops7h 10m

$182

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mar. 1/6

10:00 am-3:20 pm

1 stop4h 20m

Tampa

jue. 1/8

7:15 am-9:05 am

Nonstop2h 50m

$185

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mié. 2/4

8:20 am-4:10 pm

1 stop6h 50m

Tampa

vie. 2/6

6:50 pm-8:35 pm

Nonstop2h 45m

$187

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mar. 1/13

1:25 pm-9:05 pm

2 stops6h 40m

Tampa

jue. 1/15

3:05 pm-7:35 pm

1 stop5h 30m

$196

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

sáb. 1/24

9:55 am-1:35 pm

Nonstop2h 40m

Tampa

sáb. 1/31

11:30 am-4:55 pm

1 stop6h 25m

$196

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

jue. 1/8

8:20 am-4:10 pm

1 stop6h 50m

Tampa

jue. 1/15

11:05 am-12:55 pm

Nonstop2h 50m

$196

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

jue. 1/8

1:25 pm-9:05 pm

2 stops6h 40m

Tampa

vie. 1/16

11:05 am-12:55 pm

Nonstop2h 50m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 22 results
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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 December 5, 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 diciembre 12, 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 December 6, 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 diciembre 12, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Clearwater, such as Southwest, Delta, and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,253 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

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
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

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
8,007 reviews
Southwest
7.9
Good
4,253 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

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
3,084 reviews
Southwest
7.9
Good
4,253 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

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 2h 40m. Airlines will cover a distance of 998 mi. Generally, flights for this route are nonstop.

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

    While on average a flight from Chicago Midway Airport to Clearwater is generally $195, our data shows the cheapest flight currently is $40. When looking at the most popular route, (Chicago Midway - Tampa), you can expect to pay $99 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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Alternative routes for Midway to Clearwater

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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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$209FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$185FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$173Average$383FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$414FlexibilityNo cancel feeOn-timeN/A

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