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Midway

$77+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Apr 17 — Apr 241
Fri 4/17
Fri 4/24
1 adult, Economy
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Cheapflights Tip: The best prices from Clearwater to Chicago Midway are usually found in October or September, booked 34 days in advance, depart on a Friday or Wednesday and return on a Thursday

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 March 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Wed 4/157:50 pm
TPA
-
MDW
1 stop24h 41m
Frontier
Wed 4/222:15 pm
MDW
-
TPA
1 stop9h 11m
Frontier
Deal found 3/18$138
This eDestinos deal was found by Cheapflights users on 3/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:50 pm
TPA
-
MDW
1 stop27h 24m
Frontier
Wed 4/222:15 pm
MDW
-
TPA
1 stop9h 11m
Frontier
Deal found 3/18$147
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Tue 4/216:02 pm
TPA
-
MDW
1 stop5h 12m
Multiple Airlines
Sat 4/257:34 pm
MDW
-
TPA
1 stop11h 00m
Multiple Airlines
Deal found 3/16$149
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/306:02 pm
TPA
-
MDW
1 stop5h 17m
Multiple Airlines
Tue 5/512:27 pm
MDW
-
TPA
1 stop8h 00m
Multiple Airlines
Deal found 3/17$150
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Tue 4/218:44 am
TPA
-
MDW
1 stop11h 47m
Frontier
Thu 4/232:15 pm
MDW
-
TPA
1 stop16h 19m
Frontier
Deal found 3/17$156
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 4/236:02 pm
TPA
-
MDW
1 stop5h 17m
Multiple Airlines
Sat 4/257:34 pm
MDW
-
TPA
1 stop11h 00m
Multiple Airlines
Deal found 3/16$167
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:02 pm
TPA
-
MDW
1 stop5h 17m
Multiple Airlines
Sun 4/266:00 am
MDW
-
TPA
1 stop9h 57m
Multiple Airlines
Deal found 3/13$173
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Wed 4/157:50 pm
TPA
-
MDW
1 stop24h 41m
Multiple Airlines
Wed 4/226:15 am
MDW
-
TPA
2 stops7h 31m
Multiple Airlines
Deal found 3/18$175

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 March 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$138
(Kiwi.com)

One-way from

$77
(Kiwi.com)

Popular in

January

Cheapest in

October

Average price

$331
Provider with most accurate pricing for Tampa-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tampa-Chicago (CHI) flights.
Search Deals
From Clearwater to Chicago Midway
Search Deals
One-way flight from Clearwater to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 18, 2026.
Use the filters below to find and compare flights from Clearwater to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 4/22

11:05 am-2:55 pm

1 stop4h 50m

Chicago Midway

Sat 4/25

5:55 pm-9:30 pm

Nonstop2h 35m

$207

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 4/17

6:30 pm-8:20 pm

Nonstop2h 50m

Chicago Midway

Sun 4/19

8:50 pm-12:25 am

Nonstop2h 35m

$237

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 5/2

6:55 am-8:40 am

Nonstop2h 45m

Chicago Midway

Mon 5/4

8:30 pm-12:05 am

Nonstop2h 35m

$237

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 5/1

3:55 pm-8:35 pm

1 stop5h 40m

Chicago Midway

Mon 5/4

8:30 pm-12:05 am

Nonstop2h 35m

$243

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 4/23

8:30 am-12:20 pm

1 stop4h 50m

Chicago Midway

Sun 4/26

5:00 am-8:30 am

Nonstop2h 30m

$247

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 5/8

7:00 am-8:50 am

Nonstop2h 50m

Chicago Midway

Fri 6/5

5:15 pm-8:50 pm

Nonstop2h 35m

$315

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 4/9

7:00 am-8:50 am

Nonstop2h 50m

Chicago Midway

Sat 4/11

5:55 pm-9:30 pm

Nonstop2h 35m

$317
Quickest round-trip

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 5/23

6:55 am-8:40 am

Nonstop2h 45m

Chicago Midway

Mon 5/25

5:00 am-8:30 am

Nonstop2h 30m

$352

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 6/4

10:30 pm-12:05 am

Nonstop2h 35m

Chicago Midway

Fri 6/5

5:05 pm-12:15 am

1 stop6h 10m

$362

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 3/31

7:00 pm-11:55 pm

1 stop5h 55m

Chicago Midway

Fri 4/3

3:55 pm-8:50 pm

1 stop3h 55m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/14

Showing 1-10 of 23 resultsSorted by cheapest first
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3

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 March 13, 2026.

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, September is the cheapest month in which you can book a flight from Clearwater to Chicago Midway Airport (average of $46). Flying from Clearwater to Chicago Midway Airport in July is currently the most expensive (average of $125). 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 March 18, 2026.

It’s optimal to fly from Clearwater to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 12% 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 March 14, 2026.

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. 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 March 18, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andFrontier 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
4,320 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

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
4,320 reviews
Southwest
8.0
Very good
4,320 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

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
7.9
Good
8,288 reviews
Southwest
8.0
Very good
4,320 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

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
5.7
Fair
3,024 reviews
Southwest
8.0
Very good
4,320 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

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 4h 50m. Southwest provides one of the quickest options available for as low as $207. Clearwater and Chicago Midway Airport are separated by a distance of 998 mi.

  • What are the most reliable airlines from Clearwater to Chicago Midway Airport?

    The top 3 most reliable airlines when flying from Clearwater to Chicago Midway Airport are Southwest (64%), Volaris (59%) and Frontier (52%).

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

    Looking at all options, your cheapest flight can be booked for $49. While the most popular route (Tampa - Chicago Midway) can be booked for $180 on average, our data indicates $252 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, September is the cheapest month in which you can book a flight from Clearwater to Chicago Midway Airport (average of $46). Flying from Clearwater to Chicago Midway Airport in July is currently the most expensive (average of $125). 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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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 March 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$164FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$196FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$326FlexibilityNo cancel feeOn-time63%

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