$61+ Cheap flights from Sarasota (SRQ) 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — CHI
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Sarasota 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 Sarasota Bradenton Intl to Chicago are usually found in April or May, booked 85 days in advance, depart on a Saturday or Thursday and return on a Sunday
Cheap flight deals from Sarasota to Chicago
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Cheapest flights from Sarasota to ChicagoExplore the most affordable flight options available from Sarasota to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
Explore the most affordable flight options available from Sarasota to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
This Mytrip deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:00 am -
Nonstop2h 59m
Thu 12/101:49 pm -
Nonstop2h 45m
Deal found 10/26![Allegiant Air logo]()
$134
This CheapOair deal was found by Cheapflights users on 10/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:00 am -
Nonstop2h 59m
Sun 12/61:49 pm -
Nonstop2h 45m
Deal found 10/25![Allegiant Air logo]()
$150
This CheapOair deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/611:00 am -
Nonstop2h 59m
Thu 12/101:49 pm -
Nonstop2h 45m
Deal found 10/26![Allegiant Air logo]()
$160
This Gotogate deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:11 am -
Nonstop2h 50m
Sun 11/1511:30 am -
Nonstop2h 40m
Deal found 10/26![Allegiant Air logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:49 pm -
2 stops19h 37m
Thu 12/101:49 pm -
Nonstop2h 45m
Deal found 10/26![Multiple Airlines logo]()
$256
This CheapOair deal was found by Cheapflights users on 10/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:30 am -
Nonstop2h 54m
Mon 11/309:50 am -
Nonstop2h 38m
Deal found 10/25![Allegiant Air logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:49 pm -
2 stops19h 37m
Sun 12/61:49 pm -
Nonstop2h 45m
Deal found 10/26![Multiple Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:11 am -
Nonstop2h 50m
Sun 11/1510:30 am -
2 stops29h 51m
Deal found 10/26![Multiple Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/67:30 am -
3 stops26h 56m
Thu 12/101:49 pm -
Nonstop2h 45m
Deal found 10/26![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:11 am -
Nonstop2h 50m
Thu 11/129:30 am -
2 stops30h 51m
Deal found 10/29![Multiple Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:45 pm -
Nonstop3h 00m
Sat 12/53:45 pm -
Nonstop2h 35m
Deal found 10/29![Southwest logo]()
$291
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/101:06 pm -
Nonstop3h 24m
Sat 12/1212:59 pm -
Nonstop2h 59m
Deal found 10/28![American Airlines logo]()
$291
Best flights from Sarasota to ChicagoDiscover carefully curated flight deals from Sarasota to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
Discover carefully curated flight deals from Sarasota to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
This Booking.com deal was found by Cheapflights users on 10/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/148:30 am -
Nonstop3h 03m
Sun 1/1711:23 am -
Nonstop2h 47m
Deal found 10/25![Allegiant Air logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:49 pm -
2 stops19h 37m
Thu 12/101:49 pm -
Nonstop2h 45m
Deal found 10/26![Multiple Airlines logo]()
$256
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:45 pm -
Nonstop3h 00m
Sat 12/53:45 pm -
Nonstop2h 35m
Deal found 10/26![Southwest logo]()
$291
This CheapOair deal was found by Cheapflights users on 10/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:00 am -
Nonstop2h 59m
Sun 12/61:49 pm -
Nonstop2h 45m
Deal found 10/25![Allegiant Air logo]()
$150
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:15 pm -
1 stop5h 54m
Wed 12/93:59 pm -
1 stop6h 15m
Deal found 10/27![Delta logo]()
$311
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/164:20 pm -
Nonstop3h 12m
Mon 12/217:11 am -
Nonstop2h 58m
Deal found 10/27![United Airlines logo]()
$324
This CheapOair deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:11 am -
Nonstop2h 50m
Sun 11/1511:30 am -
Nonstop2h 40m
Deal found 10/27![Allegiant Air logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/67:30 am -
3 stops26h 56m
Thu 12/101:49 pm -
Nonstop2h 45m
Deal found 10/26![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:11 am -
Nonstop2h 50m
Thu 11/129:30 am -
2 stops30h 51m
Deal found 10/29![Multiple Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:45 pm -
1 stop5h 00m
Thu 12/175:05 am -
1 stop8h 20m
Deal found 10/29![Southwest logo]()
$311
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:00 am -
1 stop6h 47m
Fri 12/187:11 am -
Nonstop2h 58m
Deal found 10/29![United Airlines logo]()
$330
This CheapOair deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:11 am -
Nonstop2h 50m
Sun 11/811:30 am -
Nonstop2h 40m
Deal found 10/29![Allegiant Air logo]()
$282
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:55 pm -
1 stop6h 45m
Fri 12/48:05 am -
Nonstop2h 45m
Deal found 10/29![Southwest logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/108:11 am -
Nonstop3h 03m
Sun 1/175:41 pm -
2 stops26h 58m
Deal found 10/28![Allegiant Air logo]()
$287
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:18 pm -
Nonstop3h 11m
Sun 11/223:36 pm -
1 stop6h 32m
Deal found 10/26![United Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:25 pm -
Nonstop2h 45m
Fri 11/276:50 pm -
Nonstop2h 40m
Deal found 10/26![Southwest logo]()
$331
This United Airlines deal was found by Cheapflights users on 10/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/154:26 pm -
Nonstop3h 17m
Mon 1/185:50 pm -
Nonstop2h 59m
Deal found 10/25![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1612:20 pm -
2 stops7h 35m
Thu 12/241:15 pm -
2 stops6h 45m
Deal found 10/26![Southwest logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am -
1 stop6h 47m
Sun 12/63:35 pm -
1 stop6h 24m
Deal found 10/28![United Airlines logo]()
$379
This CheapOair deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:11 am -
Nonstop2h 50m
Thu 11/1210:51 am -
Nonstop2h 40m
Deal found 10/29![Allegiant Air logo]()
$345
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/156:40 pm -
Nonstop2h 55m
Mon 1/188:00 am -
Nonstop2h 45m
Deal found 10/25![Southwest logo]()
$357
This United Airlines deal was found by Cheapflights users on 10/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:28 pm -
Nonstop3h 12m
Sun 12/61:30 pm -
Nonstop2h 55m
Deal found 10/25![United Airlines logo]()
$396
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:45 pm -
Nonstop3h 00m
Sun 12/66:50 pm -
Nonstop2h 40m
Deal found 10/28![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/712:20 pm -
2 stops7h 05m
Wed 12/912:50 pm -
2 stops8h 05m
Deal found 10/28![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1311:50 am -
2 stops9h 15m
Thu 12/175:05 am -
1 stop8h 20m
Deal found 10/29![Southwest logo]()
$372
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/196:27 pm -
Nonstop3h 13m
Tue 12/296:00 pm -
Nonstop2h 59m
Deal found 10/28![United Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/1312:35 pm -
Nonstop2h 55m
Fri 1/157:40 am -
2 stops9h 20m
Deal found 10/26![Southwest logo]()
$372
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2012:18 pm -
Nonstop3h 11m
Tue 11/2411:44 am -
Nonstop2h 54m
Deal found 10/27![United Airlines logo]()
$511
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
1 stop6h 46m
Tue 11/172:30 pm -
1 stop7h 38m
Deal found 10/29![United Airlines logo]()
$514
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop6h 47m
Sun 11/157:15 am -
Nonstop2h 57m
Deal found 10/26![United Airlines logo]()
$533
Last-minute flights from Sarasota to ChicagoDiscover last-minute flight deals from Sarasota to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Sarasota to Chicago. Data last updated October 30, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 10/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:40 am -
Nonstop2h 50m
Sun 11/811:30 am -
Nonstop2h 40m
Deal found 10/25![Allegiant Air logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:11 am -
Nonstop2h 50m
Thu 11/129:30 am -
2 stops30h 51m
Deal found 10/29![Multiple Airlines logo]()
$276
This CheapOair deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:11 am -
Nonstop2h 50m
Sun 11/811:30 am -
Nonstop2h 40m
Deal found 10/29![Allegiant Air logo]()
$282
This Gotogate deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:11 am -
Nonstop2h 50m
Sun 11/1511:30 am -
Nonstop2h 40m
Deal found 10/26![Allegiant Air logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:11 am -
Nonstop2h 50m
Sun 11/1510:30 am -
2 stops29h 51m
Deal found 10/26![Multiple Airlines logo]()
$272
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:50 pm -
Nonstop3h 21m
Wed 12/21:10 pm -
Nonstop2h 59m
Deal found 10/27![American Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:35 pm -
1 stop6h 19m
Wed 12/26:00 am -
1 stop6h 23m
Deal found 10/27![Delta logo]()
$311
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:19 pm -
1 stop7h 30m
Thu 11/268:00 am -
1 stop4h 14m
Deal found 10/29![Delta logo]()
$311
This CheapOair deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:27 pm -
Nonstop2h 54m
Sun 11/221:44 pm -
Nonstop2h 38m
Deal found 10/26![Allegiant Air logo]()
$314
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:00 am -
2 stops8h 30m
Thu 11/268:40 am -
1 stop7h 15m
Deal found 10/27![Southwest logo]()
$316
This CheapOair deal was found by Cheapflights users on 10/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:30 am -
Nonstop2h 54m
Mon 11/309:50 am -
Nonstop2h 38m
Deal found 10/25![Allegiant Air logo]()
$262
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/252:40 pm -
1 stop4h 20m
Fri 11/2712:50 pm -
Nonstop2h 35m
Deal found 10/27![Southwest logo]()
$317
One-way flights from Sarasota to ChicagoSearch for one-way flight options from Sarasota to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from Sarasota to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This CheapOair deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/241:25 pm -
Nonstop2h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Allegiant Air logo]()
$61
This CheapOair deal was found by Cheapflights users on 10/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:11 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Allegiant Air logo]()
$64
This CheapOair deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:11 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Allegiant Air logo]()
$80
This CheapOair deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:00 am -
Nonstop2h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Allegiant Air logo]()
$98
This CheapOair deal was found by Cheapflights users on 10/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:50 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Allegiant Air logo]()
$109
This Mytrip deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/173:18 pm -
Nonstop2h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Allegiant Air logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/47:06 am -
2 stops41h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:16 am -
1 stop28h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Allegiant Air logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/148:01 am -
2 stops13h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$139
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2612:35 pm -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$146
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:37 pm -
Nonstop3h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![American Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/57:00 am -
2 stops17h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$150
Find flight deals from Sarasota to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Sarasota (SRQ) 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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $113 (Booking.com) |
One-way from | $61 (CheapOair) |
Popular in | June |
Cheapest in | April |
Average price | $472 |
Good round-trip deal | $267 or less |
Good one-way deal | $227 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Sarasota 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 30, 2026.
Use the filters below to find and compare flights from Sarasota to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
SarasotaChicago
SRQ Sarasota Bradenton Intl - RFD Chicago Greater Rockford
SRQRFD
Sarasota Bradenton Intl
Thu 12/24
1:25 pm-3:24 pm
Nonstop2h 59m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$61
SarasotaChicago
SRQ Sarasota Bradenton Intl - RFD Chicago Greater Rockford
SRQRFD
Sarasota Bradenton Intl
Thu 11/5
8:11 am-10:01 am
Nonstop2h 50m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$64
SarasotaChicago
SRQ Sarasota Bradenton Intl - RFD Chicago Greater Rockford
SRQRFD
Sarasota Bradenton Intl
Sun 2/7
8:30 am-10:33 am
Nonstop3h 03m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$100
SarasotaChicago
SRQ Sarasota Bradenton Intl - RFD Chicago Greater Rockford
SRQRFD
Sarasota Bradenton Intl
Sun 11/8
8:50 am-10:40 am
Nonstop2h 50m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
SarasotaChicago
SRQ Sarasota Bradenton Intl - RFD Chicago Greater Rockford
SRQRFD
Sarasota Bradenton Intl
Thu 1/14
8:30 am-10:33 am
Nonstop3h 03m
Chicago Greater Rockford
Sun 1/17
11:23 am-3:10 pm
Nonstop2h 47m
$113
SarasotaChicago
SRQ Sarasota Bradenton Intl - RFD Chicago Greater Rockford
SRQRFD
Sarasota Bradenton Intl
Thu 12/17
3:18 pm-5:17 pm
Nonstop2h 59m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$120
SarasotaChicago
SRQ Sarasota Bradenton Intl - RFD Chicago Greater Rockford
SRQRFD
Sarasota Bradenton Intl
Thu 12/3
11:00 am-12:59 pm
Nonstop2h 59m
Chicago Greater Rockford
Sun 12/6
1:49 pm-5:34 pm
Nonstop2h 45m
$150
SarasotaChicago
SRQ Sarasota Bradenton Intl - RFD Chicago Greater Rockford
SRQRFD
Sarasota Bradenton Intl
Sun 11/22
11:00 am-12:54 pm
Nonstop2h 54m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$154
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Mon 12/7
6:45 pm-10:45 pm
1 stop5h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$156
SarasotaChicago
SRQ Sarasota Bradenton Intl - ORD Chicago O'Hare Intl
SRQORD
Sarasota Bradenton Intl
Mon 12/7
2:15 pm-8:53 pm
1 stop7h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$156
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from Sarasota 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 Sarasota 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*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Sarasota-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Sarasota-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Sarasota-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Sarasota-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 Sarasota-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 Sarasota to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Sarasota with our price prediction graph.
SRQ-CHI
SRQ-RFD
SRQ-MDW
SRQ-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 Sarasota to Chicago
SRQ-CHI
SRQ-RFD
SRQ-MDW
SRQ-ORD
What is the cheapest month to book a flight from Sarasota to Chicago?
Currently, May is the cheapest month in which you can book a flight from Sarasota to Chicago (average of $364). Flying from Sarasota to Chicago in January is currently the most expensive (average of $543). 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 SRQ to CHI?
Find hourly flight availability from Sarasota 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 30, 2026.
It’s typically best to fly out from Sarasota to Chicago in the evening. Doing so could potentially save you 22% on the flight price compared to flying in the morning, which is usually more expensive.
How much does it cost to fly round-trip from Sarasota to Chicago?
Airfare is below average for this route at the moment.
Sarasota to Chicago flights typically cost between $359 and $620 in January.The cheapest round-trip price found within the last 5 days was $113 on Allegiant Air (Jan 10-Jan 17).
How far ahead should I book a flight from Sarasota to Chicago?
The price you pay for your flight from Sarasota to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 81 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Sarasota to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Sarasota to Chicago. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Sarasota to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Sarasota 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 Sarasota 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 30, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Sarasota to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.4
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 Sarasota 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Sarasota and Chicago flights
Browse other Sarasota and Chicago flight options. Last updated on October 30, 2026.
Other flights from Sarasota
Browse through other flights departing from Sarasota. Flights are based on user searches made on Cheapflights and were last updated on October 30, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Sarasota to Chicago
Discover the top 4 airlines that operate flights from Sarasota 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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$120 | Average$207 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$239 | Average$410 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$240 | Average$423 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$413 | FlexibilityNo cancel fee | On-time63% |