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Midway

$75+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Clearwater to Chicago Midway are usually found in January or March, booked 34 days in advance, depart on a Friday or Wednesday and return on a Friday

Cheap 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 December 15, 2025.

This Delta deal was found by Cheapflights users on 12/14. 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.
Thu 12/2510:00 amTPA - MDW
1 stop5h 40mDelta
Thu 1/16:00 amMDW - TPA
1 stop6h 59mDelta
Deal found 12/14$197
This Trip.com deal was found by Cheapflights users on 12/15. 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.
Wed 12/3111:48 amTPA - MDW
1 stop11h 24mFrontier
Wed 1/75:10 pmMDW - TPA
1 stop5h 18mFrontier
Deal found 12/15$216
This CheapOair deal was found by Cheapflights users on 12/14. 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.
Sun 12/216:45 amTPA - MDW
1 stop16h 05mFrontier
Sun 1/410:50 pmMDW - TPA
1 stop29h 41mFrontier
Deal found 12/14$219
This Expedia deal was found by Cheapflights users on 12/14. 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.
Wed 12/3111:48 amTPA - MDW
1 stop11h 24mFrontier
Sun 1/410:50 pmMDW - TPA
1 stop29h 41mFrontier
Deal found 12/14$233
This CheapOair deal was found by Cheapflights users on 12/13. 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.
Mon 12/295:45 amTPA - MDW
1 stop8h 36mFrontier
Mon 1/58:15 amMDW - TPA
1 stop9h 35mFrontier
Deal found 12/13$243
This Frontier deal was found by Cheapflights users on 12/13. 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.
Wed 12/3111:48 amTPA - MDW
1 stop11h 24mFrontier
Thu 1/16:33 pmMDW - TPA
1 stop4h 53mFrontier
Deal found 12/13$257
This Southwest deal was found by Cheapflights users on 12/14. 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 12/257:15 pmTPA - MDW
Nonstop2h 45mSouthwest
Wed 12/316:00 pmMDW - TPA
Nonstop2h 35mSouthwest
Deal found 12/14$262
This Expedia deal was found by Cheapflights users on 12/13. 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.
Mon 12/225:45 amTPA - MDW
1 stop8h 36mFrontier
Tue 12/302:01 pmMDW - TPA
1 stop20h 34mFrontier
Deal found 12/13$264
This Priceline deal was found by Cheapflights users on 12/13. 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.
Mon 12/225:45 amTPA - MDW
1 stop8h 36mFrontier
Fri 1/28:15 amMDW - TPA
1 stop9h 33mFrontier
Deal found 12/13$267

Find flight deals from Clearwater to Midway

Keep the following information in mind while searching for Clearwater to Midway flight deals. Data was last updated December 15, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$98
(Frontier)

One-way from

$75
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$274
Provider with most accurate pricing for Tampa-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tampa-Chicago (CHI) flights.
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From Clearwater to Chicago Midway
Search Deals
One-way flight from Clearwater to Chicago Midway
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 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 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 December 15, 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 1/15

6:50 pm-8:35 pm

Nonstop2h 45m

Chicago Midway

Tue 1/20

1:25 pm-5:00 pm

Nonstop2h 35m

$168

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 1/15

6:50 pm-8:35 pm

Nonstop2h 45m

Chicago Midway

Sat 1/17

2:30 pm-6:05 pm

Nonstop2h 35m

$178

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 1/15

6:40 am-8:25 am

Nonstop2h 45m

Chicago Midway

Sun 1/18

1:25 pm-8:15 pm

1 stop5h 50m

$184

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 2/3

8:30 am-11:59 am

1 stop4h 29m

Chicago Midway

Wed 2/11

12:48 pm-6:54 pm

1 stop5h 06m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 1/17

8:30 am-12:48 pm

1 stop5h 18m

Chicago Midway

Mon 1/19

6:14 pm-12:25 am

1 stop5h 11m

$198

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 1/31

8:30 am-12:46 pm

1 stop5h 16m

Chicago Midway

Sun 2/1

6:00 am-12:45 pm

1 stop5h 45m

$198

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 1/15

8:30 am-12:48 pm

1 stop5h 18m

Chicago Midway

Tue 1/20

12:48 pm-5:52 pm

1 stop4h 04m

$198

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 1/31

8:20 am-1:30 pm

1 stop6h 10m

Chicago Midway

Sun 2/1

6:45 am-10:30 am

Nonstop2h 45m

$198

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 1/16

11:45 am-5:37 pm

1 stop6h 52m

Chicago Midway

Sun 1/18

6:45 am-1:46 pm

1 stop6h 01m

$198

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 1/16

11:45 am-5:37 pm

1 stop6h 52m

Chicago Midway

Mon 1/19

6:14 pm-12:25 am

1 stop5h 11m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

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 December 12, 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 34 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, March is the cheapest month in which you can book a flight from Clearwater to Chicago Midway Airport (average of $41). Flying from Clearwater to Chicago Midway Airport in July is currently the most expensive (average of $126). 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 December 15, 2025.

It’s optimal to fly from Clearwater to Chicago Midway Airport in the evening. By choosing this option you can save up to 17% on the cost of your flight, compared to a flight in the morning.

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 December 13, 2025.

Travelers seeking maximum savings on their Clearwater to Chicago Midway Airport flight should consider departing on Wednesday evenings when fares are most often at their lowest. Tuesday afternoons 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 December 15, 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
7.9
Good
4,250 reviews

Overall

7.9

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
7.9
Good
8,010 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
3,082 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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 45m. Southwest provides one of the quickest options available for as low as $168. 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 $39. While the most popular route (Tampa - Chicago Midway) can be booked for $147 on average, our data indicates $196 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, March is the cheapest month in which you can book a flight from Clearwater to Chicago Midway Airport (average of $41). Flying from Clearwater to Chicago Midway Airport in July is currently the most expensive (average of $126). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 3 airlines flying from Clearwater to Midway

Discover the top 3 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$156FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$206FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$328FlexibilityNo cancel feeOn-time63%

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