$81+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
May 29 — Jun 51
Round-trip
1 adult, Economy
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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 13 days in advance, depart on a Friday or Thursday and return on a Friday
Cheap flight deals from Midway to Clearwater
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to ClearwaterExplore 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 April 29, 2026.
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 April 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 5/1611:59 am
MDW
- TPA
1 stop6h 59m
Frontier
Mon 5/185:04 pm
TPA
- MDW
1 stop19h 05m
Frontier
Deal found 4/24![Frontier logo]()
$143
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
MDW
- TPA
1 stop14h 27m
Frontier
Tue 6/304:46 pm
TPA
- MDW
1 stop19h 23m
Frontier
Deal found 4/26![Frontier logo]()
$145
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:04 pm
MDW
- TPA
1 stop8h 23m
Frontier
Wed 5/274:46 pm
TPA
- MDW
1 stop6h 16m
Frontier
Deal found 4/26![Frontier logo]()
$146
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 6/312:04 pm
MDW
- TPA
1 stop8h 23m
Frontier
Tue 6/94:46 pm
TPA
- MDW
1 stop6h 25m
Frontier
Deal found 4/25![Frontier logo]()
$149
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 5/266:00 am
MDW
- TPA
1 stop11h 51m
Frontier
Wed 5/274:46 pm
TPA
- MDW
1 stop19h 26m
Frontier
Deal found 4/27![Frontier logo]()
$153
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
MDW
- TPA
1 stop11h 51m
Frontier
Tue 6/24:46 pm
TPA
- MDW
1 stop6h 16m
Frontier
Deal found 4/26![Frontier logo]()
$157
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
MDW
- TPA
1 stop5h 35m
Frontier
Tue 5/195:04 pm
TPA
- MDW
1 stop5h 58m
Frontier
Deal found 4/26![Frontier logo]()
$158
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.
Mon 5/256:00 am
MDW
- TPA
1 stop28h 39m
Frontier
Mon 6/12:25 pm
TPA
- MDW
1 stop8h 37m
Frontier
Deal found 4/27![Frontier logo]()
$162
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:04 pm
MDW
- TPA
1 stop5h 47m
Frontier
Tue 6/24:46 pm
TPA
- MDW
1 stop6h 16m
Frontier
Deal found 4/26![Frontier logo]()
$163
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 5/1412:19 pm
MDW
- TPA
1 stop26h 50m
Frontier
Mon 5/185:04 pm
TPA
- MDW
1 stop19h 05m
Frontier
Deal found 4/27![Frontier logo]()
$165
Best flights from Midway to ClearwaterDiscover carefully curated flight deals from Midway to Clearwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 29, 2026.
Discover carefully curated flight deals from Midway to Clearwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 29, 2026.
This Southwest deal was found by Cheapflights users on 4/24. 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.
Sat 5/165:55 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Mon 5/187:00 am
TPA
- MDW
Nonstop2h 50m
Southwest
Deal found 4/24![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 4/24. 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 5/195:55 am
MDW
- TPA
Nonstop2h 30m
Southwest
Sat 5/306:55 am
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 4/24![Southwest logo]()
$249
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:50 pm
MDW
- TPA
1 stop4h 40m
Southwest
Sat 6/135:30 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 4/26![Southwest logo]()
$254
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/135:00 am
MDW
- TPA
Nonstop2h 30m
Southwest
Mon 6/155:20 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 4/29![Southwest logo]()
$256
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Sat 6/275:30 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 4/26![Southwest logo]()
$265
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/185:00 am
MDW
- TPA
Nonstop2h 25m
Southwest
Sat 6/203:05 pm
TPA
- MDW
1 stop5h 20m
Southwest
Deal found 4/27![Southwest logo]()
$266
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Tue 7/1411:55 am
TPA
- MDW
1 stop4h 55m
Southwest
Deal found 4/27![Southwest logo]()
$266
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:25 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Mon 7/205:20 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 4/27![Southwest logo]()
$271
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:20 am
MDW
- TPA
Nonstop2h 35m
Southwest
Mon 6/85:20 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 4/28![Southwest logo]()
$279
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:50 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Sun 6/78:20 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 4/25![Southwest logo]()
$300
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/52:25 pm
MDW
- TPA
1 stop4h 55m
Southwest
Sun 6/78:20 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 4/29![Southwest logo]()
$304
Last-minute flights from Midway to ClearwaterDiscover last-minute flight deals from Midway to Clearwater. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Clearwater. Data last updated April 29, 2026 and is based on user searches.
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
MDW
- TPA
1 stop5h 35m
Frontier
Tue 5/195:04 pm
TPA
- MDW
1 stop5h 58m
Frontier
Deal found 4/26![Frontier logo]()
$158
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
MDW
- TPA
1 stop5h 35m
Frontier
Wed 5/205:04 pm
TPA
- MDW
1 stop5h 58m
Frontier
Deal found 4/28![Frontier logo]()
$160
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.
Wed 5/136:00 am
MDW
- TPA
1 stop14h 27m
Frontier
Mon 5/1811:51 am
TPA
- MDW
1 stop24h 18m
Frontier
Deal found 4/27![Frontier logo]()
$166
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 5/1412:19 pm
MDW
- TPA
1 stop26h 50m
Frontier
Mon 5/185:04 pm
TPA
- MDW
1 stop19h 05m
Frontier
Deal found 4/27![Frontier logo]()
$165
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.
Thu 5/146:00 am
MDW
- TPA
1 stop14h 27m
Frontier
Sat 5/161:25 pm
TPA
- MDW
1 stop9h 37m
Frontier
Deal found 4/25![Frontier logo]()
$172
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:00 am
MDW
- TPA
1 stop9h 09m
Frontier
Tue 5/195:04 pm
TPA
- MDW
1 stop5h 58m
Frontier
Deal found 4/29![Frontier logo]()
$168
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:04 pm
MDW
- TPA
1 stop8h 23m
Frontier
Wed 5/274:46 pm
TPA
- MDW
1 stop6h 16m
Frontier
Deal found 4/26![Frontier logo]()
$146
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.
Mon 5/256:00 am
MDW
- TPA
1 stop28h 39m
Frontier
Mon 6/12:25 pm
TPA
- MDW
1 stop8h 37m
Frontier
Deal found 4/27![Frontier logo]()
$162
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 5/266:00 am
MDW
- TPA
1 stop11h 51m
Frontier
Wed 5/274:46 pm
TPA
- MDW
1 stop19h 26m
Frontier
Deal found 4/27![Frontier logo]()
$153
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
MDW
- TPA
1 stop11h 51m
Frontier
Tue 6/24:46 pm
TPA
- MDW
1 stop6h 16m
Frontier
Deal found 4/26![Frontier logo]()
$157
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.
Wed 5/276:00 am
MDW
- TPA
2 stops13h 51m
Multiple Airlines
Wed 6/34:46 pm
TPA
- MDW
1 stop6h 16m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$174
One-way flights from Midway to ClearwaterSearch for one-way flight options from Midway to Clearwater. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
Search for one-way flight options from Midway to Clearwater. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
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.
Mon 5/256:00 am
MDW
- TPA
1 stop28h 39m
Frontier
Deal found 4/27![Frontier logo]()
$81
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.
Mon 6/296:00 am
MDW
- TPA
1 stop28h 42m
Frontier
Deal found 4/27![Frontier logo]()
$82
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:20 am
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 4/29![Southwest logo]()
$85
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.
Tue 6/2312:27 pm
MDW
- TPA
1 stop5h 24m
Frontier
Deal found 4/29![Frontier logo]()
$88
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
MDW
- TPA
1 stop5h 35m
Frontier
Deal found 4/27![Frontier logo]()
$89
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:27 pm
MDW
- TPA
1 stop7h 50m
Frontier
Deal found 4/26![Frontier logo]()
$94
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:04 pm
MDW
- TPA
1 stop8h 23m
Frontier
Deal found 4/26![Frontier logo]()
$95
This iWofly 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
MDW
- TPA
1 stop9h 09m
Frontier
Deal found 4/27![Frontier logo]()
$96
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 April 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $143 (Kiwi.com) |
One-way from | $81 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $350 |
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 April 29, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Clearwater that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 5/16
5:55 pm-9:30 pm
Nonstop2h 35m
Tampa
Mon 5/18
7:00 am-8:50 am
Nonstop2h 50m
$248
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Tue 5/19
5:55 am-9:25 am
Nonstop2h 30m
Tampa
Sat 5/30
6:55 am-8:40 am
Nonstop2h 45m
$249
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 6/6
5:50 pm-11:30 pm
1 stop4h 40m
Tampa
Sat 6/13
5:30 am-7:10 am
Nonstop2h 40m
$254
Quickest round-trip
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 6/13
5:00 am-8:30 am
Nonstop2h 30m
Tampa
Mon 6/15
5:20 am-7:00 am
Nonstop2h 40m
$256
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Tue 6/23
8:15 pm-11:50 pm
Nonstop2h 35m
Tampa
Sat 6/27
5:30 am-7:10 am
Nonstop2h 40m
$265
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Thu 6/18
5:00 am-8:25 am
Nonstop2h 25m
Tampa
Sat 6/20
3:05 pm-7:25 pm
1 stop5h 20m
$266
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 7/8
8:15 pm-11:50 pm
Nonstop2h 35m
Tampa
Tue 7/14
11:55 am-3:50 pm
1 stop4h 55m
$266
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 7/11
6:25 pm-10:00 pm
Nonstop2h 35m
Tampa
Mon 7/20
5:20 am-7:00 am
Nonstop2h 40m
$271
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 6/3
9:20 am-12:55 pm
Nonstop2h 35m
Tampa
Mon 6/8
5:20 am-7:00 am
Nonstop2h 40m
$279
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sun 5/31
8:50 pm-12:25 am
Nonstop2h 35m
Tampa
Sun 6/7
8:20 pm-10:00 pm
Nonstop2h 40m
$300
Showing 1-10 of 22 resultsSorted by cheapest first
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.
MDW-TPA
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
MDW-CL9
MDW-TPA
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 April 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 17% 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 April 25, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Clearwater flight should consider departing on Monday 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 Chicago Midway Airport to Clearwater?
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 April 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.
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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.
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Midway and Clearwater flights
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Top 3 airlines flying from Midway to Clearwater
Discover the top 3 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 April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$177 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$529 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$170 | Average$372 | FlexibilityNo cancel fee | On-time63% |