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Midway

$68+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Mar 2 — Mar 91
Mon 3/2
Mon 3/9
1 adult, Economy
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Cheapflights Tip: The best prices from Clearwater to Chicago Midway are usually found in October 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 January 31, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/30. 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 2/65:45 am
TPA
-
MDW
1 stop27h 58m
Frontier
Mon 2/96:20 am
MDW
-
TPA
1 stop9h 37m
Frontier
Deal found 1/30$133
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 2/65:45 am
TPA
-
MDW
1 stop27h 58m
Frontier
Wed 3/116:05 am
MDW
-
TPA
1 stop13h 55m
Frontier
Deal found 1/30$134
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 2/55:45 am
TPA
-
MDW
1 stop17h 34m
Frontier
Fri 2/66:20 am
MDW
-
TPA
1 stop17h 06m
Frontier
Deal found 1/29$135
This Frontier deal was found by Cheapflights users on 1/29. 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.
Thu 2/195:25 am
TPA
-
MDW
1 stop7h 02m
Frontier
Mon 2/236:00 am
MDW
-
TPA
1 stop11h 26m
Frontier
Deal found 1/29$148
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Sat 2/281:15 pm
TPA
-
MDW
1 stop9h 24m
Frontier
Sat 3/76:00 am
MDW
-
TPA
1 stop26h 08m
Frontier
Deal found 1/31$153
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:15 am
TPA
-
MDW
Nonstop2h 50m
Southwest
Sat 3/79:40 pm
MDW
-
TPA
Nonstop2h 35m
Southwest
Deal found 1/30$157
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 2/65:45 am
TPA
-
MDW
1 stop27h 58m
Multiple Airlines
Wed 3/1111:25 am
MDW
-
TPA
2 stops18h 54m
Multiple Airlines
Deal found 1/30$159
This Frontier deal was found by Cheapflights users on 1/31. 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.
Sat 4/188:44 am
TPA
-
MDW
1 stop11h 47m
Frontier
Mon 4/202:20 pm
MDW
-
TPA
1 stop9h 06m
Frontier
Deal found 1/31$160
This Kiwi.com deal was found by Cheapflights users on 1/30. 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.
Tue 2/106:15 am
TPA
-
MDW
1 stop13h 52m
Multiple Airlines
Sat 2/146:00 am
MDW
-
TPA
2 stops14h 00m
Multiple Airlines
Deal found 1/30$162
This Kiwi.com deal was found by Cheapflights users on 1/30. 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.
Tue 2/176:15 am
TPA
-
MDW
1 stop13h 52m
Frontier
Wed 2/187:00 am
MDW
-
TPA
1 stop14h 29m
Frontier
Deal found 1/30$163
This Frontier deal was found by Cheapflights users on 1/30. 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 2/129:53 am
TPA
-
MDW
1 stop12h 19m
Frontier
Sat 2/216:00 am
MDW
-
TPA
1 stop11h 30m
Frontier
Deal found 1/30$165

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 January 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$133
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

June

Cheapest in

October

Average price

$231
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 ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 31, 2026.
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 3/4

7:15 am-9:05 am

Nonstop2h 50m

Chicago Midway

Sat 3/7

9:40 pm-1:15 am

Nonstop2h 35m

$157

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 3/4

6:55 pm-10:31 pm

1 stop4h 36m

Chicago Midway

Sat 3/7

4:13 pm-12:01 am

1 stop6h 48m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 3/5

6:20 am-8:10 am

Nonstop2h 50m

Chicago Midway

Sun 3/8

6:15 am-9:55 am

Nonstop2h 40m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 2/26

6:55 pm-10:31 pm

1 stop4h 36m

Chicago Midway

Mon 3/2

1:29 pm-9:46 pm

1 stop7h 17m

$209

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 2/14

7:45 pm-9:30 pm

Nonstop2h 45m

Chicago Midway

Tue 2/17

6:45 am-10:30 am

Nonstop2h 45m

$216

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 3/5

5:25 am-9:54 am

1 stop5h 29m

Chicago Midway

Sun 3/8

6:34 pm-11:53 pm

1 stop4h 19m

$217

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 2/21

5:25 am-10:21 am

1 stop5h 56m

Chicago Midway

Sat 2/28

11:06 am-5:48 pm

1 stop5h 42m

$217

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 2/17

3:45 pm-8:10 pm

1 stop5h 25m

Chicago Midway

Sat 2/21

6:15 pm-9:55 pm

Nonstop2h 40m

$220

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 2/14

1:00 pm-9:08 pm

1 stop9h 08m

Chicago Midway

Mon 2/16

2:19 pm-12:35 am

1 stop9h 16m

$249

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 3/13

10:50 pm-12:35 am

Nonstop2h 45m

Chicago Midway

Tue 3/17

4:30 pm-8:05 pm

Nonstop2h 35m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/31

Showing 1-10 of 21 results
1
2
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 January 30, 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, March is the cheapest month in which you can book a flight from Clearwater to Chicago Midway Airport (average of $43). 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 January 31, 2026.

It’s optimal to fly from Clearwater to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 16% 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 January 24, 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 January 31, 2026.
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
4,267 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
8,130 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
3,054 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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 2h 50m. Southwest provides one of the quickest options available for as low as $157. 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 Southwest (77%), Volaris (64%) and Frontier (63%).

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

    Looking at all options, your cheapest flight can be booked for $66. While the most popular route (Tampa - Chicago Midway) can be booked for $154 on average, our data indicates $215 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 $43). 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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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 January 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$155FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$196FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$322FlexibilityNo cancel feeOn-time63%

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