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Midway

$64+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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

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 October 30, 2025.

This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:36 pmTPA - MDW
1 stop23h 54mFrontier
Sun 11/166:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 10/28$103
This Booking.com deal was found by Cheapflights users on 10/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:10 amTPA - MDW
1 stop13h 29mFrontier
Fri 11/145:57 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 10/29$108
This Frontier deal was found by Cheapflights users on 10/30. 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.
Thu 11/135:01 amTPA - MDW
1 stop10h 32mFrontier
Sat 11/151:37 pmMDW - TPA
1 stop8h 06mFrontier
Deal found 10/30$110
This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/128:25 amTPA - MDW
1 stop5h 16mFrontier
Thu 11/139:15 amMDW - TPA
1 stop8h 27mFrontier
Deal found 10/29$111
This Frontier deal was found by Cheapflights users on 10/30. 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.
Fri 11/143:11 pmTPA - MDW
Nonstop2h 46mFrontier
Mon 11/176:30 amMDW - TPA
1 stop7h 14mFrontier
Deal found 10/30$112
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:11 pmTPA - MDW
Nonstop2h 46mFrontier
Sun 11/166:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 10/30$113
This Booking.com deal was found by Cheapflights users on 10/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/122:31 pmTPA - MDW
1 stop21h 59mFrontier
Sun 11/166:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 10/30$121
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/128:25 amTPA - MDW
1 stop5h 16mFrontier
Fri 11/145:57 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 10/29$122
This Frontier deal was found by Cheapflights users on 10/30. 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.
Fri 11/149:49 amTPA - MDW
1 stop5h 44mFrontier
Sat 11/156:15 amMDW - TPA
1 stop10h 22mFrontier
Deal found 10/30$127

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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$103
(CheapOair)

One-way from

$64
(Trip.com)

Popular in

June

Cheapest in

January

Average price

$280
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. 16% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 30, 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

Wed 12/3

6:15 am-8:00 am

Nonstop2h 45m

Chicago Midway

Sun 12/7

5:20 am-8:55 am

Nonstop2h 35m

$178

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 12/3

10:05 am-4:34 pm

1 stop7h 29m

Chicago Midway

Sun 12/7

5:13 pm-12:19 am

1 stop6h 06m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 12/11

8:08 pm-11:47 pm

1 stop4h 39m

Chicago Midway

Mon 1/26

6:00 am-1:48 pm

1 stop6h 48m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 12/15

5:45 am-12:34 pm

1 stop7h 49m

Chicago Midway

Mon 12/15

5:29 pm-10:54 pm

1 stop4h 25m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 12/11

6:30 am-11:55 am

1 stop6h 25m

Chicago Midway

Mon 1/19

12:48 pm-6:54 pm

1 stop5h 06m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 12/5

6:05 pm-11:47 pm

1 stop6h 42m

Chicago Midway

Sun 12/7

6:00 am-11:47 am

1 stop4h 47m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 12/12

6:05 pm-11:47 pm

1 stop6h 42m

Chicago Midway

Tue 12/16

12:50 pm-6:01 pm

1 stop4h 11m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 1/13

10:05 am-4:31 pm

1 stop7h 26m

Chicago Midway

Wed 1/14

9:34 am-3:15 pm

1 stop4h 41m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 12/12

8:08 pm-11:47 pm

1 stop4h 39m

Chicago Midway

Wed 12/17

10:49 am-6:01 pm

1 stop6h 12m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 12/12

5:30 am-11:55 am

1 stop7h 25m

Chicago Midway

Mon 12/15

6:00 am-2:00 pm

1 stop7h 00m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 24 results
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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 October 24, 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, 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 October 30, 2025.

It’s optimal to fly from Clearwater to Chicago Midway Airport in the evening. By choosing this option you can save up to 10% on the cost of your flight, compared to a flight at noon.

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 October 26, 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. Sunday mornings 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 October 30, 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
4,242 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
7,993 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
3,123 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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 $178. 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 airlines to fly from Clearwater to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $70 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $99 one-way.

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

    Looking at all options, your cheapest flight can be booked for $54. While the most popular route (Tampa - Chicago Midway) can be booked for $82 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, 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
Merrillville
Lansing
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 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$161FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$88Average$120FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$206FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$335FlexibilityNo cancel feeOn-time63%

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