$118+ Cheap flights from Tampa (TPA) 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
TPA — MDW
Aug 8 — Aug 151
Round-trip
1 adult, Economy
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Find cheap flights from Tampa 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 Tampa to Chicago Midway are usually found in October or August, booked 71 days in advance, depart on a Friday or Wednesday and return on a Friday
Cheap flight deals from Tampa to Midway
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Best
Last-minute
One-way
Cheapest flights from Tampa to MidwayExplore the most affordable flight options available from Tampa to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 9, 2026.
Explore the most affordable flight options available from Tampa to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/37:00 am
TPA
- MDW
1 stop5h 07m
Frontier
Wed 8/511:06 am
MDW
- TPA
1 stop9h 39m
Frontier
Deal found 7/8![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/610:44 pm
TPA
- MDW
2 stops24h 19m
Multiple Airlines
Wed 8/1211:06 am
MDW
- TPA
1 stop6h 29m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 7/3110:27 am
TPA
- MDW
1 stop7h 55m
Frontier
Fri 8/711:06 am
MDW
- TPA
1 stop6h 29m
Frontier
Deal found 7/9![Frontier logo]()
$226
This Southwest deal was found by Cheapflights users on 7/8. 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 8/611:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Tue 8/116:05 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/8![Southwest logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 7/3110:27 am
TPA
- MDW
1 stop7h 55m
Frontier
Thu 8/611:06 am
MDW
- TPA
1 stop6h 29m
Frontier
Deal found 7/8![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 7/4. 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 8/55:15 pm
TPA
- MDW
1 stop5h 48m
Frontier
Sat 8/811:06 am
MDW
- TPA
1 stop5h 37m
Frontier
Deal found 7/4![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 7/7. 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 10/37:00 am
TPA
- MDW
1 stop4h 58m
Frontier
Tue 10/67:25 am
MDW
- TPA
1 stop8h 53m
Frontier
Deal found 7/7![Frontier logo]()
$230
This Southwest deal was found by Cheapflights users on 7/7. 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 8/57:55 am
TPA
- MDW
1 stop5h 25m
Southwest
Wed 8/127:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 7/7![Southwest logo]()
$231
This Frontier deal was found by Cheapflights users on 7/8. 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.
Tue 8/44:46 pm
TPA
- MDW
1 stop6h 17m
Frontier
Sun 8/99:27 pm
MDW
- TPA
1 stop10h 42m
Frontier
Deal found 7/8![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 7/3010:27 am
TPA
- MDW
1 stop11h 05m
Frontier
Thu 8/611:06 am
MDW
- TPA
1 stop6h 29m
Frontier
Deal found 7/8![Frontier logo]()
$233
This Frontier deal was found by Cheapflights users on 7/8. 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 8/110:27 am
TPA
- MDW
1 stop7h 59m
Frontier
Wed 8/56:05 am
MDW
- TPA
1 stop11h 30m
Frontier
Deal found 7/8![Frontier logo]()
$234
Best flights from Tampa to MidwayDiscover carefully curated flight deals from Tampa to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 9, 2026.
Discover carefully curated flight deals from Tampa to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 9, 2026.
This Southwest deal was found by Cheapflights users on 7/7. 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 8/2011:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Mon 8/246:20 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/7![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 7/8. 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 8/221:00 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Sat 8/2911:00 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 7/8![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 7/8. 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 8/65:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Tue 8/116:05 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/8![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 7/7. 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 8/196:30 pm
TPA
- MDW
1 stop4h 20m
Southwest
Mon 8/2410:10 am
MDW
- TPA
2 stops5h 40m
Southwest
Deal found 7/7![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 7/8. 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 8/19:20 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Fri 8/75:30 pm
MDW
- TPA
1 stop4h 15m
Southwest
Deal found 7/8![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 7/4. 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 8/56:00 am
TPA
- MDW
1 stop7h 00m
Southwest
Sat 8/83:05 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/4![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 7/8. 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 10/84:40 pm
TPA
- MDW
1 stop4h 35m
Southwest
Mon 10/127:55 am
MDW
- TPA
2 stops6h 15m
Southwest
Deal found 7/8![Southwest logo]()
$360
This Southwest deal was found by Cheapflights users on 7/5. 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 8/47:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Mon 8/103:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/5![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 7/4. 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 8/126:35 pm
TPA
- MDW
1 stop5h 35m
Southwest
Sat 8/158:05 am
MDW
- TPA
1 stop5h 45m
Southwest
Deal found 7/4![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 7/6. 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 8/86:00 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Sun 8/98:20 am
MDW
- TPA
Nonstop2h 40m
Southwest
Deal found 7/6![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 7/5. 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 11/57:25 am
TPA
- MDW
Nonstop2h 50m
Southwest
Sun 11/812:50 pm
MDW
- TPA
1 stop3h 55m
Southwest
Deal found 7/5![Southwest logo]()
$379
Last-minute flights from Tampa to MidwayDiscover last-minute flight deals from Tampa to Midway. Data last updated July 9, 2026 and is based on user searches.
Discover last-minute flight deals from Tampa to Midway. Data last updated July 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 7/3010:27 am
TPA
- MDW
1 stop11h 05m
Frontier
Thu 8/611:06 am
MDW
- TPA
1 stop6h 29m
Frontier
Deal found 7/8![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 7/314:46 pm
TPA
- MDW
1 stop6h 17m
Frontier
Fri 8/711:06 am
MDW
- TPA
1 stop6h 29m
Frontier
Deal found 7/8![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 7/8. 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 8/110:27 am
TPA
- MDW
1 stop7h 59m
Frontier
Wed 8/56:05 am
MDW
- TPA
1 stop11h 30m
Frontier
Deal found 7/8![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/37:00 am
TPA
- MDW
1 stop5h 07m
Frontier
Wed 8/511:06 am
MDW
- TPA
1 stop9h 39m
Frontier
Deal found 7/8![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/34:46 pm
TPA
- MDW
1 stop6h 17m
Frontier
Fri 8/711:06 am
MDW
- TPA
1 stop6h 29m
Frontier
Deal found 7/8![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 7/9. 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.
Tue 8/47:00 am
TPA
- MDW
1 stop5h 07m
Frontier
Sun 8/99:27 pm
MDW
- TPA
1 stop10h 42m
Frontier
Deal found 7/9![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 7/4. 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 8/55:15 pm
TPA
- MDW
1 stop5h 48m
Frontier
Sat 8/811:06 am
MDW
- TPA
1 stop5h 37m
Frontier
Deal found 7/4![Frontier logo]()
$229
This Southwest deal was found by Cheapflights users on 7/7. 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 8/57:55 am
TPA
- MDW
1 stop5h 25m
Southwest
Wed 8/127:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 7/7![Southwest logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/610:44 pm
TPA
- MDW
2 stops24h 19m
Multiple Airlines
Wed 8/1211:06 am
MDW
- TPA
1 stop6h 29m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 7/8. 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 8/611:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Tue 8/116:05 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/8![Southwest logo]()
$227
This Frontier deal was found by Cheapflights users on 7/8. 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 8/1510:27 am
TPA
- MDW
1 stop7h 59m
Frontier
Tue 8/186:05 am
MDW
- TPA
1 stop11h 44m
Frontier
Deal found 7/8![Frontier logo]()
$230
One-way flights from Tampa to MidwaySearch for one-way flight options from Tampa to Midway. Find affordable one-way fares based on user searches. Data last updated July 9, 2026.
Search for one-way flight options from Tampa to Midway. Find affordable one-way fares based on user searches. Data last updated July 9, 2026.
This Southwest deal was found by Cheapflights users on 7/7. 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 10/57:50 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 7/7![Southwest logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 7/5. 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 10/37:00 am
TPA
- MDW
1 stop28h 58m
Frontier
Deal found 7/5![Frontier logo]()
$119
This Delta deal was found by Cheapflights users on 7/9. 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 9/285:48 pm
TPA
- MDW
1 stop5h 57m
Delta
Deal found 7/9![Delta logo]()
$121
This Super.com deal was found by Cheapflights users on 7/5. 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.
Sat 8/810:27 am
TPA
- MDW
1 stop7h 59m
Frontier
Deal found 7/5![Frontier logo]()
$123
This Southwest deal was found by Cheapflights users on 7/7. 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 9/1411:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Deal found 7/7![Southwest logo]()
$124
This Super.com deal was found by Cheapflights users on 7/6. 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.
Thu 8/65:40 pm
TPA
- MDW
1 stop5h 23m
Frontier
Deal found 7/6![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am
TPA
- MDW
1 stop4h 58m
Frontier
Deal found 7/7![Frontier logo]()
$127
This Southwest deal was found by Cheapflights users on 7/8. 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 10/86:55 pm
TPA
- MDW
1 stop5h 15m
Southwest
Deal found 7/8![Southwest logo]()
$128
This Expedia deal was found by Cheapflights users on 7/8. 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.
Sat 8/17:00 am
TPA
- MDW
1 stop5h 07m
Frontier
Deal found 7/8![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 7/7. 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 8/222:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Deal found 7/7![Frontier logo]()
$131
This Super.com deal was found by Cheapflights users on 7/5. 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.
Thu 7/307:00 am
TPA
- MDW
1 stop5h 07m
Frontier
Deal found 7/5![Frontier logo]()
$132
Find flight deals from Tampa to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Tampa (TPA) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $223 (Kiwi.com) |
One-way from | $118 (Southwest) |
Popular in | June |
Cheapest in | October |
Average price | $342 |
Good round-trip deal | $361 or less |
Good one-way deal | $216 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Tampa 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 July 9, 2026.
Use the filters below to find and compare flights from Tampa to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
TampaChicago
TPA - MDW
TPAMDW
Tampa
Thu 8/20
11:30 am-2:30 pm
1 stop4h 00m
Chicago Midway
Mon 8/24
6:20 pm-9:55 pm
Nonstop2h 35m
$242
Quickest round-trip
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 8/22
1:00 pm-2:40 pm
Nonstop2h 40m
Chicago Midway
Sat 8/29
11:00 am-2:30 pm
Nonstop2h 30m
$285
TampaChicago
TPA - MDW
TPAMDW
Tampa
Thu 8/6
5:15 am-6:55 am
Nonstop2h 40m
Chicago Midway
Tue 8/11
6:05 pm-9:40 pm
Nonstop2h 35m
$317
TampaChicago
TPA - MDW
TPAMDW
Tampa
Wed 8/19
6:30 pm-9:50 pm
1 stop4h 20m
Chicago Midway
Mon 8/24
10:10 am-4:50 pm
2 stops5h 40m
$323
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 8/1
9:20 pm-11:05 pm
Nonstop2h 45m
Chicago Midway
Fri 8/7
5:30 pm-10:45 pm
1 stop4h 15m
$338
TampaChicago
TPA - MDW
TPAMDW
Tampa
Wed 8/5
6:00 am-12:00 pm
1 stop7h 00m
Chicago Midway
Sat 8/8
3:05 pm-6:40 pm
Nonstop2h 35m
$359
TampaChicago
TPA - MDW
TPAMDW
Tampa
Thu 10/8
4:40 pm-8:15 pm
1 stop4h 35m
Chicago Midway
Mon 10/12
7:55 am-3:10 pm
2 stops6h 15m
$360
TampaChicago
TPA - MDW
TPAMDW
Tampa
Tue 8/4
7:35 am-9:15 am
Nonstop2h 40m
Chicago Midway
Mon 8/10
3:15 pm-6:50 pm
Nonstop2h 35m
$361
TampaChicago
TPA - MDW
TPAMDW
Tampa
Wed 8/12
6:35 pm-11:10 pm
1 stop5h 35m
Chicago Midway
Sat 8/15
8:05 am-2:50 pm
1 stop5h 45m
$369
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 8/8
6:00 pm-7:40 pm
Nonstop2h 40m
Chicago Midway
Sun 8/9
8:20 am-12:00 pm
Nonstop2h 40m
$373
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Tampa to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Tampa to Midway in July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Tampa-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tampa-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Tampa-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Tampa-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Tampa-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Tampa to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Tampa 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 Tampa to Chicago Midway Airport
How far ahead should I book a flight from Tampa to Chicago Midway Airport?
The best time to book flights from Tampa to Chicago Midway Airport is 69 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 Tampa to Chicago Midway Airport?
Currently, October is the cheapest month in which you can book a flight from Tampa to Chicago Midway Airport (average of $204). Flying from Tampa to Chicago Midway Airport in June is currently the most expensive (average of $391). 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 TPA to MDW?
Find hourly flight availability from Tampa 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 July 9, 2026.
It’s optimal to fly from Tampa to Chicago Midway Airport at noon. By choosing this option you can save up to 39% on the cost of your flight, compared to a flight in the morning.
What is the cheapest day to fly from Tampa to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Tampa to Midway. Price data was last updated on July 4, 2026.
Travelers seeking maximum savings on their Tampa to Chicago Midway Airport flight should consider departing on Friday at noon 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.
The best insider tips for Tampa to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Tampa to Chicago Midway Airport trip
Our travel experts
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 July 9, 2026.
Read through reviews of airlines operating flights from Tampa to Chicago Midway Airport, such as Southwest,Delta, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Tampa 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
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 9, 2026.
Tampa and Midway flights
Browse other Tampa and Midway flight options. Last updated on July 9, 2026.
Other flights from Tampa
Browse through other flights departing from Tampa. Flights are based on user searches made on Cheapflights and were last updated on July 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Tampa to Midway
Discover the top 4 airlines that operate flights from Tampa 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 July 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$169 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$219 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$171 | Average$331 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$202 | Average$360 | FlexibilityNo cancel fee | On-time62% |