$105+ Cheap flights from Tampa (TPA) to Chicago (CHI)
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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
TPA — CHI
Nov 4 — Nov 111
Round-trip
1 adult, Economy
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Find cheap flights from Tampa to Chicago 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 are usually found in January or February, booked 89 days in advance, depart on a Friday or Thursday and return on a Wednesday
Cheap flight deals from Tampa to Chicago
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Cheapest flights from Tampa to ChicagoExplore the most affordable flight options available from Tampa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
Explore the most affordable flight options available from Tampa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
This Southwest deal was found by Cheapflights users on 10/5. 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 11/126:05 pm -
2 stops5h 40m
Tue 11/1710:20 am -
1 stop3h 55m
Deal found 10/5![Southwest logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 11/141:36 pm -
1 stop5h 54m
Mon 11/167:55 am -
1 stop24h 55m
Deal found 10/5![Multiple Airlines logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/179:00 am -
1 stop8h 15m
Tue 12/229:23 pm -
1 stop9h 28m
Deal found 9/30![Frontier logo]()
$212
This Super.com deal was found by Cheapflights users on 10/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2210:39 pm -
Nonstop3h 04m
Mon 11/306:20 am -
Nonstop2h 45m
Deal found 10/4![Frontier logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:19 pm -
1 stop6h 28m
Sat 11/218:28 am -
1 stop6h 56m
Deal found 10/4![Frontier logo]()
$213
This Mytrip deal was found by Cheapflights users on 9/30. 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 11/181:41 pm -
1 stop5h 35m
Thu 11/191:06 pm -
2 stops18h 12m
Deal found 9/30![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 10/311:41 pm -
1 stop5h 06m
Tue 11/36:16 am -
1 stop10h 17m
Deal found 10/2![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 12/177:35 am -
Nonstop3h 13m
Thu 12/319:21 pm -
1 stop9h 30m
Deal found 10/1![Frontier logo]()
$214
This Mytrip deal was found by Cheapflights users on 9/30. 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.
Tue 10/279:10 am -
2 stops15h 37m
Thu 10/296:16 am -
1 stop10h 06m
Deal found 9/30![Frontier logo]()
$215
This Mytrip deal was found by Cheapflights users on 9/30. 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.
Sat 11/2110:39 pm -
Nonstop3h 04m
Mon 11/233:55 pm -
2 stops15h 23m
Deal found 9/30![Frontier logo]()
$215
This Mytrip deal was found by Cheapflights users on 10/1. 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.
Tue 10/279:10 am -
2 stops15h 37m
Fri 10/306:16 am -
1 stop15h 19m
Deal found 10/1![Frontier logo]()
$216
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:59 pm -
1 stop5h 34m
Sat 11/212:52 pm -
1 stop5h 42m
Deal found 10/1![Frontier logo]()
$216
Best flights from Tampa to ChicagoDiscover carefully curated flight deals from Tampa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
Discover carefully curated flight deals from Tampa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
This Southwest deal was found by Cheapflights users on 10/4. 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 11/47:20 am -
Nonstop2h 45m
Wed 11/116:15 am -
Nonstop2h 40m
Deal found 10/4![Southwest logo]()
$281
This United Airlines deal was found by Cheapflights users on 10/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:35 pm -
Nonstop3h 05m
Fri 10/305:45 pm -
Nonstop2h 58m
Deal found 10/1![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 9/30. 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 11/212:17 pm -
1 stop4h 47m
Mon 11/231:31 pm -
1 stop6h 24m
Deal found 9/30![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 10/4. 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 11/183:00 pm -
1 stop5h 55m
Wed 11/259:15 pm -
Nonstop2h 45m
Deal found 10/4![Southwest logo]()
$287
This United Airlines deal was found by Cheapflights users on 10/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:15 am -
1 stop6h 23m
Wed 12/211:00 am -
Nonstop2h 57m
Deal found 10/3![United Airlines logo]()
$302
This Southwest deal was found by Cheapflights users on 10/3. 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 12/151:20 pm -
Nonstop2h 40m
Mon 1/47:45 am -
Nonstop2h 40m
Deal found 10/3![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 10/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/912:30 pm -
Nonstop3h 05m
Wed 11/119:00 am -
1 stop6h 06m
Deal found 10/2![United Airlines logo]()
$306
This Southwest deal was found by Cheapflights users on 10/1. 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 10/247:35 am -
Nonstop2h 40m
Sun 11/15:00 am -
Nonstop2h 35m
Deal found 10/1![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 10/2. 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 11/113:00 pm -
1 stop5h 55m
Sat 11/148:00 am -
2 stops8h 45m
Deal found 10/2![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 10/1. 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 12/176:50 pm -
Nonstop2h 45m
Wed 12/309:15 pm -
Nonstop2h 40m
Deal found 10/1![Southwest logo]()
$303
This United Airlines deal was found by Cheapflights users on 10/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:00 am -
1 stop6h 26m
Fri 10/307:15 am -
Nonstop2h 55m
Deal found 10/1![United Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 10/3. 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 12/147:20 am -
Nonstop2h 45m
Mon 1/46:50 pm -
Nonstop2h 35m
Deal found 10/3![Southwest logo]()
$304
This United Airlines deal was found by Cheapflights users on 10/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:45 am -
Nonstop3h 05m
Sat 11/287:15 am -
Nonstop2h 55m
Deal found 10/4![United Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 10/2. 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 11/226:25 am -
1 stop5h 00m
Tue 11/245:15 am -
Nonstop2h 35m
Deal found 10/2![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 10/4. 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 11/114:00 pm -
2 stops6h 30m
Mon 11/161:15 pm -
2 stops6h 35m
Deal found 10/4![Southwest logo]()
$312
This United Airlines deal was found by Cheapflights users on 10/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:33 pm -
Nonstop3h 05m
Tue 10/208:50 am -
1 stop5h 26m
Deal found 10/4![United Airlines logo]()
$438
This Southwest deal was found by Cheapflights users on 10/4. 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.
Sat 12/267:20 pm -
Nonstop2h 50m
Fri 1/13:50 pm -
1 stop5h 20m
Deal found 10/4![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 10/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/181:54 pm -
Nonstop3h 03m
Sun 11/297:15 am -
Nonstop2h 56m
Deal found 10/4![United Airlines logo]()
$442
This United Airlines deal was found by Cheapflights users on 10/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/94:30 pm -
Nonstop3h 08m
Fri 10/161:55 pm -
Nonstop2h 48m
Deal found 10/2![United Airlines logo]()
$471
This United Airlines deal was found by Cheapflights users on 10/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 pm -
Nonstop3h 05m
Tue 10/275:45 pm -
Nonstop2h 58m
Deal found 10/4![United Airlines logo]()
$503
This United Airlines deal was found by Cheapflights users on 9/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 pm -
Nonstop3h 05m
Mon 10/1912:59 pm -
Nonstop2h 48m
Deal found 9/30![United Airlines logo]()
$581
Last-minute flights from Tampa to ChicagoDiscover last-minute flight deals from Tampa to Chicago. Data last updated October 5, 2026 and is based on user searches.
Discover last-minute flight deals from Tampa to Chicago. Data last updated October 5, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 9/30. 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.
Tue 10/279:10 am -
2 stops15h 37m
Thu 10/296:16 am -
1 stop10h 06m
Deal found 9/30![Frontier logo]()
$215
This Mytrip deal was found by Cheapflights users on 10/1. 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.
Tue 10/279:10 am -
2 stops15h 37m
Fri 10/306:16 am -
1 stop15h 19m
Deal found 10/1![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 10/311:41 pm -
1 stop5h 06m
Tue 11/36:16 am -
1 stop10h 17m
Deal found 10/2![Frontier logo]()
$214
This Mytrip deal was found by Cheapflights users on 10/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:08 am -
1 stop12h 22m
Thu 11/57:55 am -
2 stops13h 40m
Deal found 10/4![Frontier logo]()
$214
This Southwest deal was found by Cheapflights users on 10/5. 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 11/126:05 pm -
2 stops5h 40m
Tue 11/1710:20 am -
1 stop3h 55m
Deal found 10/5![Southwest logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 11/141:36 pm -
1 stop5h 54m
Mon 11/167:55 am -
1 stop24h 55m
Deal found 10/5![Multiple Airlines logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:19 pm -
1 stop6h 28m
Sat 11/218:28 am -
1 stop6h 56m
Deal found 10/4![Frontier logo]()
$213
This Trip.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/171:05 pm -
1 stop5h 42m
Sat 11/218:28 am -
1 stop6h 56m
Deal found 10/1![Frontier logo]()
$212
This Mytrip deal was found by Cheapflights users on 9/30. 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 11/181:41 pm -
1 stop5h 35m
Thu 11/191:06 pm -
2 stops18h 12m
Deal found 9/30![Frontier logo]()
$213
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:59 pm -
1 stop5h 34m
Sat 11/212:52 pm -
1 stop5h 42m
Deal found 10/1![Frontier logo]()
$216
This Mytrip deal was found by Cheapflights users on 9/30. 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.
Sat 11/2110:39 pm -
Nonstop3h 04m
Mon 11/233:55 pm -
2 stops15h 23m
Deal found 9/30![Frontier logo]()
$215
This Super.com deal was found by Cheapflights users on 10/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2210:39 pm -
Nonstop3h 04m
Mon 11/306:20 am -
Nonstop2h 45m
Deal found 10/4![Frontier logo]()
$212
One-way flights from Tampa to ChicagoSearch for one-way flight options from Tampa to Chicago. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
Search for one-way flight options from Tampa to Chicago. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
This Trip.com deal was found by Cheapflights users on 10/1. 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$105
This Trip.com deal was found by Cheapflights users on 10/1. 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.
Wed 10/211:52 pm -
1 stop5h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 10/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:54 pm -
1 stop5h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 10/205:57 pm -
2 stops22h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 10/213:11 pm -
1 stop25h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Multiple Airlines logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 10/283:11 pm -
2 stops18h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$108
This CheapOair deal was found by Cheapflights users on 10/2. 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 12/1712:04 pm -
1 stop5h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Frontier logo]()
$109
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:39 pm -
Nonstop3h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$109
This Trip.com deal was found by Cheapflights users on 9/30. 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 10/235:57 pm -
1 stop6h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 10/3. 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 10/2311:11 pm -
1 stop17h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Multiple Airlines logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:57 pm -
1 stop6h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 10/192:34 pm -
2 stops34h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$111
Find flight deals from Tampa to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Tampa (TPA) to Chicago (CHI). 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 October 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $211 (Southwest) |
One-way from | $105 (Trip.com) |
Popular in | July |
Cheapest in | January |
Average price | $264 |
Good round-trip deal | $180 or less |
Good one-way deal | $72 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Tampa to Chicago 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 October 5, 2026.
Use the filters below to find and compare flights from Tampa to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Mon 11/16
8:45 am-2:15 pm
1 stop6h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$110
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Mon 12/7
3:55 pm-7:40 pm
1 stop4h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$110
Quickest round-trip
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Thu 11/19
1:20 pm-3:00 pm
Nonstop2h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Mon 11/2
6:50 pm-8:35 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Thu 12/3
7:20 am-9:05 am
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Wed 12/9
1:37 pm-3:42 pm
Nonstop3h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Sat 11/7
12:30 pm-2:35 pm
Nonstop3h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Wed 11/4
7:20 am-9:05 am
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Wed 12/9
11:15 am-1:00 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Sat 2/27
6:20 am-10:07 am
1 stop4h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Showing 1-10 of 44 resultsSorted by cheapest first
Compare providers for flights from Tampa to Chicago
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 Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Tampa-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tampa-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Tampa-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Tampa-Chicago 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 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 Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Tampa with our price prediction graph.
TPA-CHI
TPA-MDW
TPA-ORD
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
TPA-CHI
TPA-MDW
TPA-ORD
What is the cheapest month to book a flight from Tampa to Chicago?
Currently, February is the cheapest month in which you can book a flight from Tampa to Chicago (average of $201). Flying from Tampa to Chicago in July is currently the most expensive (average of $377). 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 CHI?
Find hourly flight availability from Tampa to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 5, 2026.
One of the essential ways to save on airfare from Tampa to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 17% on airfare.
Weekly flight availability from Tampa to Chicago
Explore weekly flight availability from Tampa to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 5, 2026.
The most flights from TPA to CHI are scheduled on a Friday (45 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (19 on average).
How much does it cost to fly round-trip from Tampa to Chicago?
Airfare is typical for this route at the moment.
Tampa to Chicago flights typically cost between $190 and $372 in November.The cheapest round-trip price found within the last 5 days was $211 on Southwest (Nov 12-Nov 17).
What’s the top layover airport for flights from Tampa to Chicago?
Share of 1-stop round-trip flights from Tampa to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.
Atlanta (ATL) – chosen by Cheapflights users on 75% of 1-stop itineraries from Tampa to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from Tampa to Chicago?
Average round-trip fare for 1-stop flights from Tampa to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $263.
What’s the fastest layover option from Tampa to Chicago?
Shortest average travel time for 1-stop one-way flights from Tampa to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 5h 01m.
Which airport typically offers the quickest layover for flights from Tampa to Chicago?
Average layover duration for 1-stop one-way flights from Tampa to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Atlanta (ATL) offer the fastest connection on this route, with an average layover time of 2h 47m.
How far ahead should I book a flight from Tampa to Chicago?
Booking 63 days in advance of your planned departure date is, on average, the best time to get cheap flights from Tampa to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Tampa to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Tampa to Chicago. Price data was last updated on October 3, 2026.
Travelers seeking maximum savings on their Tampa to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Tampa to Chicago 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 trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 5, 2026.
Read through reviews of airlines operating flights from Tampa to Chicago, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
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 Tampa to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 5, 2026.
Complete your trip
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Tampa and Chicago flights
Browse other Tampa and Chicago flight options. Last updated on October 5, 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 October 5, 2026.
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Tampa to Chicago flights
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Top 6 airlines flying from Tampa to Chicago
Discover the top 6 airlines that operate flights from Tampa to Chicago. 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 October 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$57 | Average$216 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$280 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$330 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$354 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$158 | Average$319 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$179 | Average$369 | FlexibilityNo cancel fee | On-time69% |