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Midway

$73+ 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 6/23. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
May 30 — Jun 61
Sat 5/30
Sat 6/6
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 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 April 30, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/25. 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 5/274:46 pm
TPA
-
MDW
1 stop6h 16m
Frontier
Mon 6/112:04 pm
MDW
-
TPA
1 stop8h 23m
Frontier
Deal found 4/25$149
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/274:46 pm
TPA
-
MDW
1 stop6h 16m
Frontier
Tue 6/212:27 pm
MDW
-
TPA
1 stop5h 24m
Frontier
Deal found 4/28$150
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:25 pm
TPA
-
MDW
1 stop8h 37m
Frontier
Mon 6/16:00 am
MDW
-
TPA
1 stop28h 39m
Frontier
Deal found 4/29$151
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/262:25 pm
TPA
-
MDW
1 stop8h 37m
Frontier
Mon 6/112:04 pm
MDW
-
TPA
1 stop5h 47m
Frontier
Deal found 4/28$152
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/282:25 pm
TPA
-
MDW
1 stop8h 37m
Frontier
Tue 6/212:27 pm
MDW
-
TPA
1 stop8h 00m
Frontier
Deal found 4/27$153
This Trip.com deal was found by Cheapflights users on 4/27. 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 5/274:46 pm
TPA
-
MDW
1 stop6h 16m
Frontier
Sat 5/3011:59 am
MDW
-
TPA
1 stop6h 59m
Frontier
Deal found 4/27$158
This Frontier deal was found by Cheapflights users on 4/26. 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.
Mon 5/117:05 am
TPA
-
MDW
1 stop5h 04m
Frontier
Mon 5/1812:04 pm
MDW
-
TPA
1 stop8h 23m
Frontier
Deal found 4/26$160
This Trip.com deal was found by Cheapflights users on 4/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/262:25 pm
TPA
-
MDW
1 stop8h 37m
Frontier
Tue 6/212:27 pm
MDW
-
TPA
1 stop5h 24m
Frontier
Deal found 4/28$162
This Trip.com deal was found by Cheapflights users on 4/27. 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 5/274:46 pm
TPA
-
MDW
1 stop6h 16m
Frontier
Wed 6/312:04 pm
MDW
-
TPA
1 stop8h 23m
Frontier
Deal found 4/27$164
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/128:17 am
TPA
-
MDW
1 stop14h 45m
Frontier
Tue 5/1912:24 pm
MDW
-
TPA
1 stop8h 03m
Frontier
Deal found 4/27$166

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 April 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$149
(Kiwi.com)

One-way from

$73
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$314
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. 14% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 30, 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

Tue 7/28

9:55 pm-11:35 pm

Nonstop2h 40m

Chicago Midway

Tue 8/11

6:05 pm-9:40 pm

Nonstop2h 35m

$205

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 8/11

5:35 pm-7:10 pm

Nonstop2h 35m

Chicago Midway

Tue 9/29

9:05 am-2:55 pm

1 stop4h 50m

$215

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 5/25

5:26 am-10:00 am

1 stop5h 34m

Chicago Midway

Thu 6/4

12:53 pm-6:51 pm

1 stop4h 58m

$219

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 6/23

5:15 am-10:09 am

1 stop5h 54m

Chicago Midway

Sat 6/27

1:21 pm-9:11 pm

1 stop6h 50m

$229

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 6/10

5:15 am-10:09 am

1 stop5h 54m

Chicago Midway

Tue 7/7

5:10 pm-12:29 am

1 stop6h 19m

$229
Quickest round-trip

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 7/8

9:55 pm-11:35 pm

Nonstop2h 40m

Chicago Midway

Tue 7/14

5:30 am-9:00 am

Nonstop2h 30m

$241

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 6/23

9:55 pm-11:35 pm

Nonstop2h 40m

Chicago Midway

Wed 7/1

5:30 am-9:00 am

Nonstop2h 30m

$241

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 5/16

6:55 am-8:40 am

Nonstop2h 45m

Chicago Midway

Tue 5/19

4:45 pm-8:20 pm

Nonstop2h 35m

$244

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 5/27

3:55 pm-5:40 pm

Nonstop2h 45m

Chicago Midway

Tue 6/2

4:45 pm-8:20 pm

Nonstop2h 35m

$256
Cheapest one-way

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 5/23

4:17 pm-9:09 pm

1 stop5h 52m

$110

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 20 resultsSorted by cheapest first
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

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 April 30, 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 in the evening.

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 April 25, 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.

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

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 April 30, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andJetBlue 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
4,317 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

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
8.0
Very good
4,317 reviews
Southwest
8.0
Very good
4,317 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

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.
Delta
7.9
Good
8,464 reviews
Southwest
8.0
Very good
4,317 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

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
7.2
Good
2,970 reviews
Southwest
8.0
Very good
4,317 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

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
5.7
Fair
2,970 reviews
Southwest
8.0
Very good
4,317 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

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 2h 40m. Southwest provides one of the quickest options available for as low as $205. 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 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 (69%), Southwest (62%) and Volaris (55%).

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

    Looking at all options, your cheapest flight can be booked for $84. While the most popular route (Tampa - Chicago Midway) can be booked for $184 on average, our data indicates $259 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 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 April 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$156FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$196FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$333FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$202Average$350FlexibilityNo cancel feeOn-time62%

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