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$71+ 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$143
(Kiwi.com)

One-way from

$71
(Kiwi.com)

Popular in

May

Cheapest in

January

Average price

$248
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 ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 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 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 June 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Thu 8/215:01 amTPA - MDW
1 stop6h 07mFrontier
Mon 8/259:10 amMDW - TPA
1 stop5h 13mFrontier
Deal found 6/9$143
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.
Tue 8/52:50 pmTPA - MDW
Nonstop2h 35mSouthwest
Tue 8/126:10 pmMDW - TPA
Nonstop2h 40mSouthwest
Deal found 6/10$157
This Delta deal was found by Cheapflights users on 6/12. 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 8/96:30 amTPA - MDW
1 stop4h 15mDelta
Wed 8/136:04 amMDW - TPA
1 stop4h 23mDelta
Deal found 6/12$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 June 12, 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

Thu 8/21

5:01 am-10:08 am

1 stop6h 07m

Chicago Midway

Mon 8/25

9:10 am-3:23 pm

1 stop5h 13m

$143

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 8/5

2:50 pm-4:25 pm

Nonstop2h 35m

Chicago Midway

Tue 8/12

6:10 pm-9:50 pm

Nonstop2h 40m

$157

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 8/9

8:50 am-11:58 am

1 stop4h 08m

Chicago Midway

Thu 8/14

6:04 am-12:30 pm

1 stop5h 26m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 8/21

5:01 am-10:08 am

1 stop6h 07m

$71

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 9/22

9:05 pm-10:45 pm

Nonstop2h 40m

$79

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 7/4

6:10 am-12:29 pm

1 stop7h 19m

$111

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sun 9/21

5:30 am-12:00 pm

2 stops31h 30m

$145

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 9, 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 June 12, 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 June 8, 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.

Weekly flight availability from Clearwater to Chicago Midway Airport

Explore weekly flight availability from Clearwater to Midway. 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 CL9 to MDW are scheduled on a Tuesday (13 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 Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Frontier from Clearwater to Chicago to help guide your decision. Users can see the overall rating for each airline as well as how each is rated 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
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
4,287 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
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
7,946 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
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
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
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 $111 one-way.

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

    Looking at all options, your cheapest flight can be booked for $48. While the most popular route (Tampa - Chicago Midway) can be booked for $157 on average our data indicates $171 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 Clearwater?

Book flights to Clearwater if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$67Average$165FlexibilityNo cancel feeOn-time65%
FrontierCheapest$76Average$166FlexibilityNo cancel feeOn-time62%
DeltaCheapest$138Average$325FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$160Average$350FlexibilityNo cancel feeOn-time63%

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