$112+ Cheap flights from Clearwater, FL to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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Find cheap flights from Clearwater to Midway 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 Clearwater to Chicago Midway are usually found in October or November, booked 60 days in advance, depart on a Friday or Wednesday and return on a Wednesday
Cheap flight deals from Clearwater to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Clearwater to MidwayExplore 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 September 17, 2026.
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 September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:20 am -
1 stop4h 00m
Mon 10/199:00 pm -
Nonstop2h 35m
Deal found 9/13![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 9/16. 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 10/2711:20 am -
1 stop4h 00m
Fri 10/309:00 pm -
Nonstop2h 35m
Deal found 9/16![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:51 pm -
1 stop4h 42m
Mon 11/96:00 am -
1 stop7h 15m
Deal found 9/14![Delta logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/155:57 pm -
1 stop6h 46m
Sun 10/186:40 pm -
1 stop16h 05m
Deal found 9/14![Frontier logo]()
$213
This Southwest deal was found by Cheapflights users on 9/15. 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 10/272:35 pm -
2 stops6h 15m
Mon 11/26:30 pm -
1 stop4h 00m
Deal found 9/15![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 9/16. 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 10/137:40 am -
1 stop5h 45m
Fri 10/169:00 pm -
Nonstop2h 35m
Deal found 9/16![Southwest logo]()
$215
This Frontier deal was found by Cheapflights users on 9/16. 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 10/211:52 pm -
1 stop10h 51m
Sun 10/256:24 am -
1 stop9h 50m
Deal found 9/16![Frontier logo]()
$216
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Wed 10/145:57 pm -
1 stop6h 46m
Wed 10/213:30 pm -
2 stops19h 15m
Deal found 9/16![Frontier logo]()
$217
This Southwest deal was found by Cheapflights users on 9/16. 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 10/237:50 pm -
Nonstop2h 45m
Mon 10/269:00 pm -
Nonstop2h 35m
Deal found 9/16![Southwest logo]()
$218
This Frontier deal was found by Cheapflights users on 9/16. 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 10/77:15 am -
1 stop11h 36m
Mon 10/126:15 am -
1 stop9h 59m
Deal found 9/16![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/312:52 pm -
1 stop5h 59m
Mon 10/56:46 pm -
1 stop21h 32m
Deal found 9/14![Frontier logo]()
$220
This Expedia deal was found by Cheapflights users on 9/14. 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.
Wed 10/211:52 pm -
1 stop10h 51m
Thu 10/226:22 am -
1 stop9h 52m
Deal found 9/14![Frontier logo]()
$221
Best flights from Clearwater to MidwayDiscover carefully curated flight deals from Clearwater to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
Discover carefully curated flight deals from Clearwater to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/14. 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 2/115:50 am -
1 stop4h 35m
Sat 2/134:05 pm -
1 stop4h 20m
Deal found 9/14![Southwest logo]()
$224
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:20 pm -
1 stop6h 34m
Sat 12/54:08 pm -
1 stop5h 07m
Deal found 9/13![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 9/15. 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 10/207:20 am -
Nonstop2h 40m
Tue 10/201:00 pm -
1 stop4h 20m
Deal found 9/15![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 9/15. 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 10/212:35 pm -
2 stops6h 15m
Sat 10/248:05 am -
1 stop5h 00m
Deal found 9/15![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 9/15. 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 1/610:25 am -
1 stop5h 35m
Sun 1/108:15 am -
1 stop6h 00m
Deal found 9/15![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/107:20 pm -
1 stop4h 35m
Mon 1/1110:35 am -
1 stop5h 36m
Deal found 9/13![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 9/16. 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 1/810:25 am -
1 stop5h 35m
Sun 1/1011:10 am -
Nonstop2h 30m
Deal found 9/16![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 9/16. 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 11/181:20 pm -
Nonstop2h 40m
Sun 11/225:00 am -
Nonstop2h 35m
Deal found 9/16![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 9/15. 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 12/116:05 pm -
2 stops5h 35m
Sun 12/136:30 pm -
1 stop4h 00m
Deal found 9/15![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 9/15. 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 1/158:35 am -
2 stops6h 10m
Tue 1/198:10 am -
2 stops6h 55m
Deal found 9/15![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/44:00 pm -
2 stops6h 25m
Sun 12/612:50 pm -
1 stop3h 55m
Deal found 9/13![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 9/16. 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 11/227:25 am -
Nonstop2h 50m
Thu 11/261:55 pm -
Nonstop2h 35m
Deal found 9/16![Southwest logo]()
$347
Last-minute flights from Clearwater to MidwayDiscover last-minute flight deals from Clearwater to Midway. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Clearwater to Midway. Data last updated September 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/312:52 pm -
1 stop5h 59m
Mon 10/56:46 pm -
1 stop21h 32m
Deal found 9/14![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 9/16. 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 10/77:15 am -
1 stop11h 36m
Mon 10/126:15 am -
1 stop9h 59m
Deal found 9/16![Frontier logo]()
$219
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:00 am -
1 stop7h 47m
Sat 10/171:27 pm -
1 stop7h 35m
Deal found 9/16![Delta logo]()
$212
This Southwest deal was found by Cheapflights users on 9/16. 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 10/137:40 am -
1 stop5h 45m
Fri 10/169:00 pm -
Nonstop2h 35m
Deal found 9/16![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:20 am -
1 stop4h 00m
Mon 10/199:00 pm -
Nonstop2h 35m
Deal found 9/13![Southwest logo]()
$210
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Wed 10/145:57 pm -
1 stop6h 46m
Wed 10/213:30 pm -
2 stops19h 15m
Deal found 9/16![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/155:57 pm -
1 stop6h 46m
Sun 10/186:40 pm -
1 stop16h 05m
Deal found 9/14![Frontier logo]()
$213
This Frontier deal was found by Cheapflights users on 9/16. 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 10/211:52 pm -
1 stop10h 51m
Sun 10/256:24 am -
1 stop9h 50m
Deal found 9/16![Frontier logo]()
$216
This Expedia deal was found by Cheapflights users on 9/14. 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.
Wed 10/211:52 pm -
1 stop10h 51m
Thu 10/226:22 am -
1 stop9h 52m
Deal found 9/14![Frontier logo]()
$221
This Southwest deal was found by Cheapflights users on 9/16. 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 10/237:50 pm -
Nonstop2h 45m
Mon 10/269:00 pm -
Nonstop2h 35m
Deal found 9/16![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 9/16. 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 10/2711:20 am -
1 stop4h 00m
Fri 10/309:00 pm -
Nonstop2h 35m
Deal found 9/16![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 9/15. 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 10/272:35 pm -
2 stops6h 15m
Mon 11/26:30 pm -
1 stop4h 00m
Deal found 9/15![Southwest logo]()
$214
One-way flights from Clearwater to MidwaySearch for one-way flight options from Clearwater to Midway. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
Search for one-way flight options from Clearwater to Midway. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/127:59 pm -
1 stop28h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$112
This Southwest deal was found by Cheapflights users on 9/14. 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.
Mon 10/56:55 pm -
1 stop5h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$113
This Southwest deal was found by Cheapflights users on 9/14. 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 10/157:50 pm -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$114
This Southwest deal was found by Cheapflights users on 9/16. 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 10/237:05 am -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 11/175:11 pm -
2 stops19h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$118
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Fri 11/65:57 pm -
2 stops18h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$119
This Super.com deal was found by Cheapflights users on 9/16. 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 10/95:57 pm -
1 stop5h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 9/14. 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 10/145:57 pm -
1 stop6h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2110:49 pm -
2 stops19h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$122
This CheapOair deal was found by Cheapflights users on 9/14. 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.
Thu 10/85:57 pm -
1 stop6h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$124
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $210 (Southwest) |
One-way from | $112 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $259 |
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 7,457,451 searches. Data last updated September 17, 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
Cheapest round-trip
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Thu 11/12
5:10 am-10:24 am
1 stop6h 14m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$113
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Thu 10/15
7:50 pm-9:35 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$113
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Mon 11/9
5:10 pm-8:15 pm
1 stop4h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$119
Quickest round-trip
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Tue 10/20
7:20 am-9:00 am
Nonstop2h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Fri 11/13
6:05 pm-10:45 pm
2 stops5h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$143
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Tue 11/24
7:20 pm-11:40 pm
1 stop5h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Tue 10/13
11:03 am-4:14 pm
1 stop6h 11m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$151
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Sun 11/1
4:35 pm-6:20 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$156
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Mon 10/19
5:40 pm-10:00 pm
1 stop5h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$166
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Fri 9/25
6:00 pm-11:44 pm
1 stop6h 44m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$180
Showing 1-10 of 23 resultsSorted by cheapest first
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.
TPA-MDW
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
CL9-MDW
TPA-MDW
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 September 17, 2026.
It’s optimal to fly from Clearwater to Chicago Midway Airport in the evening. By choosing this option you can save up to 20% on the cost of your flight, compared to a flight in the morning.
How much does it cost to fly round-trip from Clearwater to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Clearwater to Chicago Midway Airport flights typically cost between $230 and $330 in October.The cheapest round-trip price found within the last 5 days was $210 on Southwest (Oct 14-Oct 19).
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 September 12, 2026.
Travelers seeking maximum savings on their Clearwater to Chicago Midway Airport flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday 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 September 17, 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.
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$211 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$219 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$194 | Average$365 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$244 | Average$360 | FlexibilityNo cancel fee | On-time62% |