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Midway

$92+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Jul 15 — Jul 221
Wed 7/15
Wed 7/22
1 adult, Economy
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Cheapflights Tip: The best prices from Clearwater to Chicago Midway are usually found in October or August, booked 71 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 June 15, 2026.

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.
Wed 7/159:55 pm
TPA
-
MDW
Nonstop2h 45m
Southwest
Wed 7/228:15 pm
MDW
-
TPA
Nonstop2h 40m
Southwest
Deal found 6/10$209
This Travelocity deal was found by Cheapflights users on 6/11. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:00 am
TPA
-
MDW
1 stop5h 07m
Frontier
Wed 11/1812:03 pm
MDW
-
TPA
1 stop9h 54m
Frontier
Deal found 6/11$210
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/34:46 pm
TPA
-
MDW
1 stop6h 17m
Frontier
Wed 8/56:05 am
MDW
-
TPA
1 stop15h 10m
Frontier
Deal found 6/10$213
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:55 am
TPA
-
MDW
Nonstop2h 40m
Southwest
Tue 8/116:05 pm
MDW
-
TPA
Nonstop2h 35m
Southwest
Deal found 6/11$215
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/152:25 pm
TPA
-
MDW
1 stop8h 38m
Frontier
Wed 7/226:05 am
MDW
-
TPA
1 stop14h 11m
Frontier
Deal found 6/10$217
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:55 am
TPA
-
MDW
1 stop6h 10m
Southwest
Tue 7/145:25 am
MDW
-
TPA
Nonstop2h 30m
Southwest
Deal found 6/11$219
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/222:25 pm
TPA
-
MDW
1 stop8h 38m
Frontier
Wed 8/56:05 am
MDW
-
TPA
1 stop11h 30m
Frontier
Deal found 6/10$220
This Mytrip deal was found by Cheapflights users on 6/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2810:27 am
TPA
-
MDW
1 stop7h 24m
Frontier
Tue 8/412:11 pm
MDW
-
TPA
1 stop8h 05m
Frontier
Deal found 6/13$221
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:46 pm
TPA
-
MDW
1 stop6h 25m
Frontier
Thu 9/1012:03 pm
MDW
-
TPA
1 stop9h 54m
Frontier
Deal found 6/10$223
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/72:10 pm
TPA
-
MDW
1 stop8h 53m
Frontier
Tue 8/1111:06 am
MDW
-
TPA
1 stop6h 29m
Frontier
Deal found 6/10$225
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/84:46 pm
TPA
-
MDW
1 stop6h 17m
Frontier
Tue 8/412:11 pm
MDW
-
TPA
1 stop5h 41m
Frontier
Deal found 6/11$226

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 June 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(Southwest)

One-way from

$92
(Trip.com)

Popular in

March

Cheapest in

October

Average price

$361
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. 13% potential increase in price ($47 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 June 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 June 15, 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 8/5

7:55 am-12:20 pm

1 stop5h 25m

Chicago Midway

Tue 8/11

6:05 pm-9:40 pm

Nonstop2h 35m

$231

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 7/25

5:30 am-7:10 am

Nonstop2h 40m

Chicago Midway

Wed 7/29

8:15 pm-11:55 pm

Nonstop2h 40m

$279

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 7/15

11:55 am-3:50 pm

1 stop4h 55m

Chicago Midway

Sun 7/19

9:20 pm-12:55 am

Nonstop2h 35m

$301

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 7/29

10:40 am-12:20 pm

Nonstop2h 40m

Chicago Midway

Wed 7/29

1:25 pm-5:05 pm

Nonstop2h 40m

$349
Quickest round-trip

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 8/4

5:35 pm-7:10 pm

Nonstop2h 35m

Chicago Midway

Wed 8/5

7:30 am-11:00 am

Nonstop2h 30m

$349

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 11/25

7:20 pm-11:35 pm

1 stop5h 15m

Chicago Midway

Sun 11/29

5:10 am-11:05 am

1 stop4h 55m

$368

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 7/24

5:20 am-7:00 am

Nonstop2h 40m

Chicago Midway

Mon 7/27

5:00 am-8:25 am

Nonstop2h 25m

$373

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 12/11

6:50 pm-8:35 pm

Nonstop2h 45m

Chicago Midway

Mon 12/14

6:20 am-10:00 am

Nonstop2h 40m

$373

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 9/7

8:25 am-10:05 am

Nonstop2h 40m

Chicago Midway

Thu 9/17

12:10 pm-3:45 pm

Nonstop2h 35m

$373

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 7/31

8:00 am-9:40 am

Nonstop2h 40m

Chicago Midway

Mon 8/3

5:00 am-8:25 am

Nonstop2h 25m

$373

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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

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 15, 2026.

It’s optimal to fly from Clearwater to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 11% on the cost of your flight, compared to a flight in the evening.

How much does it cost to fly round-trip from Clearwater to Chicago Midway Airport?

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, 2026.

Travelers seeking maximum savings on their Clearwater to Chicago Midway Airport flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday 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 June 15, 2026.
Get a feel of what it's like to fly with Southwest,JetBlue, 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
7.9
Good
4,238 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,238 reviews
Southwest
7.9
Good
4,238 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.1
Good
2,981 reviews
Southwest
7.9
Good
4,238 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,883 reviews
Southwest
7.9
Good
4,238 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 5h 25m. Southwest provides one of the quickest options available for as low as $231. 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 Frontier (80%), Volaris (80%) and Southwest (68%).

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

    Looking at all options, your cheapest flight can be booked for $99. While the most popular route (Tampa - Chicago Midway) can be booked for $272 on average, our data indicates $333 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.

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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 June 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$166FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$351FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$202Average$360FlexibilityNo cancel feeOn-time62%

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