HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Clearwater

$63+ Cheap flights from Midway (MDW) to Clearwater, FL

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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Clearwater with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Chicago Midway to Clearwater are usually found in September or October, booked 85 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Midway to Clearwater

Cheapest flights from Midway to Clearwater
Explore the most affordable flight options available from Midway to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 2/41:20 pm
MDW
-
TPA
1 stop5h 41m
Frontier
Wed 2/114:12 pm
TPA
-
MDW
1 stop20h 15m
Frontier
Deal found 1/27$130
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/41:20 pm
MDW
-
TPA
1 stop5h 41m
Frontier
Thu 2/55:45 am
TPA
-
MDW
1 stop7h 00m
Frontier
Deal found 1/28$133
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 2/41:20 pm
MDW
-
TPA
1 stop5h 41m
Frontier
Wed 2/186:15 am
TPA
-
MDW
1 stop13h 52m
Frontier
Deal found 1/27$135
This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
-
TPA
1 stop4h 57m
Frontier
Sat 2/281:15 pm
TPA
-
MDW
1 stop9h 24m
Frontier
Deal found 1/26$138
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/116:15 am
MDW
-
TPA
1 stop17h 10m
Frontier
Thu 2/265:55 am
TPA
-
MDW
1 stop11h 21m
Frontier
Deal found 1/28$141
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 2/41:20 pm
MDW
-
TPA
1 stop5h 41m
Multiple Airlines
Tue 2/1010:05 am
TPA
-
MDW
2 stops10h 02m
Multiple Airlines
Deal found 1/27$145
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/257:00 am
MDW
-
TPA
1 stop12h 47m
Frontier
Sat 2/281:15 pm
TPA
-
MDW
1 stop9h 24m
Frontier
Deal found 1/28$147
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
-
TPA
1 stop11h 26m
Frontier
Thu 2/269:53 am
TPA
-
MDW
1 stop12h 19m
Frontier
Deal found 1/28$148
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 3/176:00 am
MDW
-
TPA
1 stop17h 26m
Frontier
Tue 3/245:30 am
TPA
-
MDW
1 stop16h 24m
Frontier
Deal found 1/28$150
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 2/41:20 pm
MDW
-
TPA
1 stop5h 41m
Multiple Airlines
Wed 2/188:30 am
TPA
-
MDW
2 stops11h 37m
Multiple Airlines
Deal found 1/27$151
This Trip.com deal was found by Cheapflights users on 1/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
-
TPA
1 stop4h 57m
Frontier
Mon 3/25:25 am
TPA
-
MDW
1 stop15h 22m
Frontier
Deal found 1/26$152

Find flight deals from Midway to Clearwater

Keep the following information in mind while searching for Midway to Clearwater flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$138
(CheapOair)

One-way from

$63
(Trip.com)

Popular in

February

Cheapest in

September

Average price

$231
Provider with most accurate pricing for Chicago (CHI)-Tampa flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Tampa flights.
Search Deals
From Chicago Midway to Clearwater
Search Deals
One-way flight from Chicago Midway to Clearwater
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($15 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 Midway to Clearwater 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 29, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Clearwater that are best for you.

Fly from

Midway

Fly to

Clearwater

Route

Depart

Return

Price

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/3

5:40 pm-9:15 pm

Nonstop2h 35m

Tampa

Wed 3/11

7:00 am-8:50 am

Nonstop2h 50m

$168

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 3/4

1:25 pm-8:15 pm

1 stop5h 50m

Tampa

Sat 3/7

6:30 am-8:20 am

Nonstop2h 50m

$183

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/17

10:45 am-6:12 pm

1 stop6h 27m

Tampa

Tue 3/31

5:30 am-9:56 am

1 stop5h 26m

$217

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 2/14

6:15 pm-9:55 pm

Nonstop2h 40m

Tampa

Sat 2/21

6:50 am-8:35 am

Nonstop2h 45m

$227

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 2/23

4:55 pm-10:50 pm

1 stop4h 55m

Tampa

Thu 2/26

6:55 pm-8:40 pm

Nonstop2h 45m

$228

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 4/8

7:25 am-2:05 pm

1 stop5h 40m

Tampa

Wed 4/15

7:15 am-9:05 am

Nonstop2h 50m

$228

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 2/24

5:40 pm-9:15 pm

Nonstop2h 35m

Tampa

Tue 3/3

1:55 pm-3:40 pm

Nonstop2h 45m

$238

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sun 2/15

9:55 am-3:00 pm

1 stop4h 05m

Tampa

Wed 2/18

9:50 am-1:10 pm

1 stop4h 20m

$248

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 3/14

6:34 pm-11:53 pm

1 stop4h 19m

Tampa

Wed 3/18

4:55 pm-10:31 pm

1 stop6h 36m

$252

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/17

12:47 pm-6:12 pm

1 stop4h 25m

Tampa

Fri 3/27

6:00 am-12:29 pm

1 stop7h 29m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 23 results
1
2
3

Best time to book a flight from Midway to Clearwater

Have a flexible travel schedule? Discover the best time to fly to Clearwater from Midway 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 Chicago Midway Airport to Clearwater

How far ahead should I book a flight from Chicago Midway Airport to Clearwater?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Clearwater. Price data was last updated on January 23, 2026.

The best time to book flights from Chicago Midway Airport to Clearwater is 85 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago Midway Airport to Clearwater?

Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Clearwater (average of $56). Flying from Chicago Midway Airport to Clearwater in June is currently the most expensive (average of $167). 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 MDW to CL9?

Find hourly flight availability from Midway to Clearwater. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

When flying from Chicago Midway Airport to Clearwater, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 13% versus a flight in the evening.

What is the cheapest day to fly from Chicago Midway Airport to Clearwater?

Use this chart to determine the cheapest time to fly round-trip from Midway to Clearwater. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Clearwater flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Clearwater

Get insights into the airlines that provide service to Clearwater. 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 Clearwater. Reviews last updated January 29, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Clearwater, such as Southwest and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Midway to Clearwater. 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 Chicago Midway Airport to Clearwater?

    Departing from Chicago Midway Airport to Clearwater will take you 2h 35m. Airlines will cover a distance of 998 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Clearwater one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $43. Southwest flights start at $88 while deals on Delta start at $98 one-way.

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

    Consider Volaris (75%), Southwest (73%) or Frontier (66%) when booking your flight. These represent the most reliable airlines when flying from Chicago Midway Airport to Clearwater.

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

    While on average a flight from Chicago Midway Airport to Clearwater is generally $211, our data shows the cheapest flight currently is $60. When looking at the most popular route, (Chicago Midway - Tampa), you can expect to pay $138 for that flight.

  • Can I find deals for flights from Midway to Clearwater that include hotel bookings?

    Yes. In addition to deals on Midway to Clearwater flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Clearwater?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Clearwater.

  • Can I find deals for business class flights from Midway to Clearwater?

    Yes. Cheapflights offers flight deals from Midway to Clearwater 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 Chicago Midway Airport to Clearwater?

    Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Clearwater (average of $56). Flying from Chicago Midway Airport to Clearwater in June is currently the most expensive (average of $167). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Clearwater

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Fort Lauderdale flights
O'Hare Intl to West Palm Beach flights
Midway to Miami flights
Midway to Orlando flights
O'Hare Intl to Sarasota flights
Midway to Fort Myers flights
Midway to Tampa flights
O'Hare Intl to Key West flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Pensacola flights
Midway to West Palm Beach flights
O'Hare Intl to Panama City flights
Midway to Sarasota flights
Rockford to Orlando Sanford Intl flights
Midway to Key West flights
Midway to Panama City flights
Midway to Jacksonville flights
Midway to Pensacola flights
Rockford to St Petersburg flights
O'Hare Intl to Valparaiso flights
O'Hare Intl to Daytona Beach flights
Rockford to Punta Gorda flights
O'Hare Intl to Melbourne flights
Midway to Daytona Beach flights
Midway to Punta Gorda flights
O'Hare Intl to Punta Gorda flights
O'Hare Intl to Tallahassee flights
Midway to Valparaiso flights
O'Hare Intl to Gainesville flights
O'Hare Intl to St Petersburg flights
Midway to Melbourne flights
Midway to Gainesville flights
Midway to Tallahassee flights
Midway to Orlando Sanford Intl flights
O'Hare Intl to Orlando Sanford Intl flights
O'Hare Intl to Valdosta flights
Midway to Valdosta flights
O'Hare Intl to Destin flights

Top 4 airlines flying from Midway to Clearwater

Discover the top 4 airlines that operate flights from Midway to Clearwater. 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 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$35Average$131FlexibilityNo cancel feeOn-time65%
FrontierCheapest$68Average$199FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$551FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$178Average$378FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.