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Midway

$63+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
out 11 — out 181
sáb 10/11
sáb 10/18
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 Monday 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 setembro 11, 2025.

Round-trip from

$103
(Cheapflightsfares)

One-way from

$63
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$239
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. 14% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 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 setembro 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 10/310:55 amTPA - MDW
Nonstop2h 49mFrontier
dom 10/56:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/11$103
This CheapOair deal was found by Cheapflights users on 9/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 10/242:22 pmTPA - MDW
Nonstop2h 47mFrontier
dom 10/265:20 amMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/9$104
This Frontier deal was found by Cheapflights users on 9/9. 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.
sex 10/310:55 amTPA - MDW
Nonstop2h 49mFrontier
seg 10/66:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/9$105
This Trip.com deal was found by Cheapflights users on 9/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 9/2810:55 amTPA - MDW
Nonstop2h 49mFrontier
dom 10/56:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/8$110
This Frontier deal was found by Cheapflights users on 9/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 9/2210:55 amTPA - MDW
Nonstop2h 49mFrontier
seg 9/296:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/8$115
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 10/172:22 pmTPA - MDW
Nonstop2h 47mFrontier
dom 10/195:20 amMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/10$122
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 10/302:15 pmTPA - MDW
1 stop7h 16mFrontier
dom 11/26:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/10$125
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 10/101:13 pmTPA - MDW
1 stop12h 11mFrontier
sex 10/179:45 amMDW - TPA
Nonstop2h 37mFrontier
Deal found 9/10$126
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 10/234:58 pmTPA - MDW
1 stop7h 22mFrontier
dom 10/265:20 amMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/9$127

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 setembro 11, 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

sex 10/24

8:10 pm-9:50 pm

Nonstop2h 40m

Chicago Midway

ter 10/28

6:55 am-10:25 am

Nonstop2h 30m

$140

TampaChicago

TPA - MDW

TPAMDW

Tampa

qui 11/27

6:00 am-7:45 am

Nonstop2h 45m

Chicago Midway

ter 12/2

6:00 pm-9:35 pm

Nonstop2h 35m

$147

TampaChicago

TPA - MDW

TPAMDW

Tampa

seg 11/3

7:15 pm-9:00 pm

Nonstop2h 45m

Chicago Midway

ter 11/4

6:00 pm-9:35 pm

Nonstop2h 35m

$149

TampaChicago

TPA - MDW

TPAMDW

Tampa

qui 10/23

6:50 am-8:30 am

Nonstop2h 40m

Chicago Midway

dom 10/26

6:55 am-10:25 am

Nonstop2h 30m

$153

TampaChicago

TPA - MDW

TPAMDW

Tampa

qui 10/2

6:00 am-3:58 pm

1 stop10h 58m

Chicago Midway

seg 10/6

5:33 pm-11:29 pm

1 stop4h 56m

$154

TampaChicago

TPA - MDW

TPAMDW

Tampa

qua 12/3

7:15 pm-9:00 pm

Nonstop2h 45m

Chicago Midway

sáb 12/6

9:45 am-4:00 pm

1 stop5h 15m

$162

TampaChicago

TPA - MDW

TPAMDW

Tampa

ter 10/21

7:05 pm-8:45 pm

Nonstop2h 40m

Chicago Midway

sex 10/31

4:50 pm-8:20 pm

Nonstop2h 30m

$163

TampaChicago

TPA - MDW

TPAMDW

Tampa

sex 9/26

10:55 am-12:44 pm

Nonstop2h 49m

Chicago Midway

seg 9/29

6:21 am-9:57 am

Nonstop2h 36m

$164

TampaChicago

TPA - MDW

TPAMDW

Tampa

sáb 11/8

7:05 am-8:50 am

Nonstop2h 45m

Chicago Midway

ter 11/11

12:00 pm-8:55 pm

1 stop7h 55m

$167

TampaChicago

TPA - MDW

TPAMDW

Tampa

sex 12/5

7:15 pm-9:00 pm

Nonstop2h 45m

Chicago Midway

seg 12/8

6:40 am-1:40 pm

1 stop6h 00m

$173

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 20 results
1
2

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 August 29, 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 setembro 11, 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 September 7, 2025.

Travelers seeking maximum savings on their Clearwater to Chicago Midway Airport flight should consider departing on Sunday afternoons 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 setembro 11, 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
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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.

  • How long is the flight from Clearwater to Chicago Midway Airport?

    A quick flight from Clearwater to Chicago Midway Airport can take about 2h 40m. Southwest provides one of the quickest options available for as low as $140. Clearwater and Chicago Midway Airport are separated by a distance of 998 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Looking at all options, your cheapest flight can be booked for $25. While the most popular route (Tampa - Chicago Midway) can be booked for $124 on average, our data indicates $164 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
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Clearwater to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 setembro 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$53Average$167FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$88Average$120FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$214FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$337FlexibilityNo cancel feeOn-time63%

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