$109+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
TPA — MDW
Sep 24 — Oct 11
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 November, booked 60 days in advance, depart on a Friday or Wednesday and return on a Wednesday
Cheap flight deals from Tampa to Midway
Cheapest
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 August 25, 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 August 25, 2026.
This CheapOair deal was found by Cheapflights users on 8/23. 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.
Fri 9/256:00 pm -
1 stop6h 44m
Mon 9/286:25 am -
1 stop10h 00m
Deal found 8/23![Frontier logo]()
$203
This Trip.com deal was found by Cheapflights users on 8/23. 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.
Thu 11/55:57 pm -
1 stop6h 50m
Mon 11/96:16 am -
1 stop10h 06m
Deal found 8/23![Frontier logo]()
$205
This CheapOair deal was found by Cheapflights users on 8/21. 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.
Fri 9/186:00 pm -
1 stop6h 44m
Fri 9/256:25 am -
1 stop10h 00m
Deal found 8/21![Frontier logo]()
$206
This Southwest deal was found by Cheapflights users on 8/24. 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.
Thu 10/157:50 pm -
Nonstop2h 45m
Mon 10/195:05 am -
Nonstop2h 30m
Deal found 8/24![Southwest logo]()
$209
This Frontier deal was found by Cheapflights users on 8/21. 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 11/146:29 pm -
1 stop6h 18m
Sun 11/156:16 am -
1 stop10h 06m
Deal found 8/21![Frontier logo]()
$211
This Trip.com deal was found by Cheapflights users on 8/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:15 am -
1 stop11h 31m
Mon 9/286:25 am -
1 stop10h 00m
Deal found 8/24![Frontier logo]()
$212
This Travelocity deal was found by Cheapflights users on 8/25. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:57 pm -
1 stop6h 50m
Sun 11/156:16 am -
1 stop10h 06m
Deal found 8/25![Frontier logo]()
$214
This Southwest deal was found by Cheapflights users on 8/21. 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 9/1212:30 pm -
1 stop5h 30m
Mon 9/147:55 pm -
Nonstop2h 35m
Deal found 8/21![Southwest logo]()
$215
This Expedia deal was found by Cheapflights users on 8/23. 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.
Tue 10/67:15 am -
1 stop11h 31m
Tue 10/136:15 am -
1 stop11h 09m
Deal found 8/23![Frontier logo]()
$216
This Frontier deal was found by Cheapflights users on 8/21. 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 10/56:00 pm -
1 stop6h 44m
Thu 10/86:15 am -
1 stop9h 59m
Deal found 8/21![Frontier logo]()
$218
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 August 25, 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 August 25, 2026.
This Southwest deal was found by Cheapflights users on 8/22. 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
Mon 10/195:05 am -
Nonstop2h 30m
Deal found 8/22![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 8/20. 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.
Sun 11/226:00 am -
1 stop7h 35m
Tue 12/15:09 pm -
1 stop6h 16m
Deal found 8/20![Delta logo]()
$260
This Southwest deal was found by Cheapflights users on 8/24. 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 9/155:35 pm -
Nonstop2h 35m
Thu 9/177:55 pm -
Nonstop2h 35m
Deal found 8/24![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 8/24. 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 11/146:35 am -
2 stops7h 20m
Tue 11/1710:20 am -
1 stop3h 55m
Deal found 8/24![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 8/20. 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 9/207:35 am -
Nonstop2h 40m
Thu 9/247:55 pm -
Nonstop2h 35m
Deal found 8/20![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 8/21. 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 9/105:50 pm -
1 stop5h 35m
Tue 9/157:40 am -
2 stops6h 10m
Deal found 8/21![Southwest logo]()
$250
This Southwest deal was found by Cheapflights users on 8/24. 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.
Wed 9/2310:35 am -
1 stop6h 15m
Wed 9/307:40 am -
2 stops6h 10m
Deal found 8/24![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 8/24. 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.
Mon 9/216:20 am -
1 stop6h 55m
Mon 9/287:55 pm -
Nonstop2h 35m
Deal found 8/24![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 8/23. 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 9/185:15 am -
Nonstop2h 40m
Mon 9/217:55 pm -
Nonstop2h 35m
Deal found 8/23![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 8/20. 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 11/239:00 am -
1 stop5h 45m
Tue 12/16:00 am -
1 stop6h 25m
Deal found 8/20![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 8/21. 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 9/3010:35 am -
1 stop5h 45m
Sun 10/46:55 am -
Nonstop2h 30m
Deal found 8/21![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 8/23. 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 10/17:50 pm -
Nonstop2h 45m
Sun 10/46:55 am -
Nonstop2h 30m
Deal found 8/23![Southwest logo]()
$276
Last-minute flights from Tampa to MidwayDiscover last-minute flight deals from Tampa to Midway. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from Tampa to Midway. Data last updated August 25, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 8/22. 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 9/1112:59 pm -
1 stop11h 45m
Mon 9/146:25 am -
1 stop10h 00m
Deal found 8/22![Frontier logo]()
$221
This Southwest deal was found by Cheapflights users on 8/20. 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 9/115:15 am -
Nonstop2h 40m
Mon 9/147:55 pm -
Nonstop2h 35m
Deal found 8/20![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 8/21. 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 9/1212:30 pm -
1 stop5h 30m
Mon 9/147:55 pm -
Nonstop2h 35m
Deal found 8/21![Southwest logo]()
$215
This CheapOair deal was found by Cheapflights users on 8/21. 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.
Fri 9/186:00 pm -
1 stop6h 44m
Fri 9/256:25 am -
1 stop10h 00m
Deal found 8/21![Frontier logo]()
$206
This Frontier deal was found by Cheapflights users on 8/21. 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.
Sun 9/206:00 pm -
1 stop6h 44m
Thu 9/246:25 am -
1 stop10h 00m
Deal found 8/21![Frontier logo]()
$211
This Southwest deal was found by Cheapflights users on 8/24. 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.
Wed 9/237:35 am -
Nonstop2h 40m
Wed 9/3010:10 am -
1 stop6h 00m
Deal found 8/24![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 8/23. 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 9/245:15 am -
Nonstop2h 40m
Tue 9/297:30 am -
Nonstop2h 30m
Deal found 8/23![Southwest logo]()
$209
This Trip.com deal was found by Cheapflights users on 8/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:15 am -
1 stop11h 31m
Mon 9/286:25 am -
1 stop10h 00m
Deal found 8/24![Frontier logo]()
$212
This CheapOair deal was found by Cheapflights users on 8/23. 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.
Fri 9/256:00 pm -
1 stop6h 44m
Mon 9/286:25 am -
1 stop10h 00m
Deal found 8/23![Frontier logo]()
$203
This Expedia deal was found by Cheapflights users on 8/21. 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.
Fri 9/256:00 pm -
1 stop6h 44m
Sun 9/276:25 am -
1 stop10h 00m
Deal found 8/21![Frontier logo]()
$214
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 August 25, 2026.
Search for one-way flight options from Tampa to Midway. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Sun 10/115:57 pm -
1 stop6h 46m
Deal found 8/20![Frontier logo]()
$109
This Southwest deal was found by Cheapflights users on 8/20. 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 9/1212:30 pm -
1 stop5h 30m
Deal found 8/20![Southwest logo]()
$110
This Super.com deal was found by Cheapflights users on 8/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:00 pm -
1 stop6h 44m
Deal found 8/24![Frontier logo]()
$114
This Southwest deal was found by Cheapflights users on 8/24. 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.
Mon 10/197:10 pm -
1 stop5h 45m
Deal found 8/24![Southwest logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Sun 9/62:25 pm -
1 stop9h 22m
Deal found 8/24![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/48:07 pm -
1 stop27h 40m
Deal found 8/23![Frontier logo]()
$117
This Southwest deal was found by Cheapflights users on 8/24. 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.
Fri 10/97:50 pm -
Nonstop2h 45m
Deal found 8/24![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 8/23. 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 9/198:15 am -
2 stops7h 05m
Deal found 8/23![Southwest logo]()
$120
This Southwest deal was found by Cheapflights users on 8/24. 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.
Thu 9/105:15 am -
Nonstop2h 40m
Deal found 8/24![Southwest logo]()
$121
This Frontier deal was found by Cheapflights users on 8/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:08 am -
1 stop11h 37m
Deal found 8/24![Frontier logo]()
$122
This Priceline deal was found by Cheapflights users on 8/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:57 pm -
1 stop6h 50m
Deal found 8/24![Frontier logo]()
$123
This CheapOair deal was found by Cheapflights users on 8/22. 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.
Mon 10/125:57 pm -
1 stop6h 46m
Deal found 8/22![Frontier logo]()
$124
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 August 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $203 (CheapOair) |
One-way from | $109 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $300 |
Good round-trip deal | $253 or less |
Good one-way deal | $181 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 7,457,451 searches. Data last updated August 25, 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 Tampa - MDW Chicago Midway
TPAMDW
Tampa
Thu 10/15
7:50 pm-9:35 pm
Nonstop2h 45m
Chicago Midway
Mon 10/19
5:05 am-8:35 am
Nonstop2h 30m
$209
Quickest round-trip
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Tue 9/15
5:35 pm-7:10 pm
Nonstop2h 35m
Chicago Midway
Thu 9/17
7:55 pm-11:30 pm
Nonstop2h 35m
$209
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Sat 11/14
6:35 am-12:55 pm
2 stops7h 20m
Chicago Midway
Tue 11/17
10:20 am-3:15 pm
1 stop3h 55m
$230
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Sun 9/20
7:35 am-9:15 am
Nonstop2h 40m
Chicago Midway
Thu 9/24
7:55 pm-11:30 pm
Nonstop2h 35m
$240
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Thu 9/10
5:50 pm-10:25 pm
1 stop5h 35m
Chicago Midway
Tue 9/15
7:40 am-2:50 pm
2 stops6h 10m
$250
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Sun 11/22
6:00 am-12:35 pm
1 stop7h 35m
Chicago Midway
Tue 12/1
5:09 pm-12:25 am
1 stop6h 16m
$260
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Wed 9/23
10:35 am-3:50 pm
1 stop6h 15m
Chicago Midway
Wed 9/30
7:40 am-2:50 pm
2 stops6h 10m
$265
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Mon 9/21
6:20 am-12:15 pm
1 stop6h 55m
Chicago Midway
Mon 9/28
7:55 pm-11:30 pm
Nonstop2h 35m
$269
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Fri 9/18
5:15 am-6:55 am
Nonstop2h 40m
Chicago Midway
Mon 9/21
7:55 pm-11:30 pm
Nonstop2h 35m
$272
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Mon 11/23
9:00 am-1:45 pm
1 stop5h 45m
Chicago Midway
Tue 12/1
6:00 am-1:25 pm
1 stop6h 25m
$273
Showing 1-10 of 21 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 August.
| 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 59 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 March is currently the most expensive (average of $384). 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 August 25, 2026.
It’s optimal to fly from Tampa to Chicago Midway Airport at noon. By choosing this option you can save up to 31% 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 August 22, 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 August 25, 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.
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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
Complete your trip
Flights by cabin class
Midway flight routes
Other flight options
Other flights from Tampa
Popular flights
Alternative routes for Tampa to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Tampa to Midway by cabin class
Find flights from Tampa to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 August 25, 2026.
Tampa and Midway flights
Browse other Tampa and Midway flight options. Last updated on August 25, 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 August 25, 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 7,457,451 searches. Data last updated August 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$219 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$197 | Average$338 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$202 | Average$360 | FlexibilityNo cancel fee | On-time62% |