$81+ Cheap flights from Sarasota (SRQ) to Chicago (CHI)
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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — CHI
Sep 29 — Oct 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 September or October, booked 26 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 August 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 August 30, 2026.
This Southwest deal was found by Cheapflights users on 8/26. 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 9/225:00 pm -
2 stops6h 25m
Tue 9/291:40 pm -
Nonstop2h 35m
Deal found 8/26![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 8/27. 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 9/235:55 pm -
Nonstop2h 40m
Mon 9/2812:20 pm -
Nonstop2h 35m
Deal found 8/27![Southwest logo]()
$237
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:03 am -
1 stop5h 10m
Tue 11/31:23 pm -
1 stop5h 33m
Deal found 8/25![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 8/27. 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 9/246:50 am -
2 stops6h 30m
Fri 9/2512:20 pm -
Nonstop2h 35m
Deal found 8/27![Southwest logo]()
$242
This CheapOair deal was found by Cheapflights users on 8/27. 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 9/39:15 am -
Nonstop2h 50m
Sun 9/1311:55 am -
Nonstop2h 40m
Deal found 8/27![Allegiant Air logo]()
$242
This Mytrip deal was found by Cheapflights users on 8/26. 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.
Sun 10/48:30 am -
Nonstop2h 52m
Sun 10/1111:30 am -
Nonstop2h 37m
Deal found 8/26![Allegiant Air logo]()
$245
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:01 am -
Nonstop2h 50m
Sun 10/1811:30 am -
Nonstop2h 37m
Deal found 8/25![Allegiant Air logo]()
$246
This Southwest deal was found by Cheapflights users on 8/27. 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.
Fri 9/2511:45 am -
1 stop7h 30m
Mon 9/283:20 pm -
1 stop5h 15m
Deal found 8/27![Southwest logo]()
$247
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:53 pm -
1 stop6h 45m
Tue 11/35:27 am -
1 stop6h 25m
Deal found 8/25![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Thu 9/174:25 pm -
Nonstop3h 10m
Tue 9/2211:10 am -
Nonstop2h 59m
Deal found 8/27![United Airlines logo]()
$248
This Southwest deal was found by Cheapflights users on 8/27. 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.
Fri 10/238:30 pm -
1 stop4h 25m
Mon 10/261:10 pm -
2 stops8h 45m
Deal found 8/27![Southwest logo]()
$252
This United Airlines deal was found by Cheapflights users on 8/26. 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.
Wed 9/304:20 pm -
Nonstop3h 11m
Sat 10/103:00 pm -
1 stop7h 30m
Deal found 8/26![United Airlines logo]()
$253
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 August 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 August 30, 2026.
This Southwest deal was found by Cheapflights users on 8/27. 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 9/235:55 pm -
Nonstop2h 40m
Mon 9/2812:20 pm -
Nonstop2h 35m
Deal found 8/27![Southwest logo]()
$237
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:01 am -
Nonstop2h 50m
Sun 10/1811:30 am -
Nonstop2h 37m
Deal found 8/25![Allegiant Air logo]()
$246
This Delta deal was found by Cheapflights users on 8/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/213:32 pm -
1 stop6h 58m
Tue 12/296:40 am -
1 stop6h 47m
Deal found 8/26![Delta logo]()
$288
This United Airlines deal was found by Cheapflights users on 8/27. 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 12/46:28 pm -
Nonstop3h 12m
Mon 12/710:45 am -
Nonstop2h 56m
Deal found 8/27![United Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 10/48:30 am -
Nonstop2h 52m
Sun 10/1110:30 am -
3 stops33h 25m
Deal found 8/26![Multiple Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 8/27. 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.
Mon 12/217:15 am -
Nonstop2h 50m
Tue 12/299:50 am -
1 stop7h 50m
Deal found 8/27![Southwest logo]()
$290
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:35 pm -
1 stop5h 09m
Mon 9/286:05 am -
1 stop5h 14m
Deal found 8/25![Delta logo]()
$298
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/234:20 pm -
Nonstop3h 11m
Mon 10/2612:59 pm -
1 stop9h 09m
Deal found 8/25![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 8/27. 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.
Wed 9/306:00 am -
1 stop4h 49m
Fri 10/26:05 am -
1 stop5h 14m
Deal found 8/27![Delta logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Thu 9/1710:46 am -
2 stops23h 06m
Sun 9/2011:55 am -
Nonstop2h 40m
Deal found 8/28![Allegiant Air logo]()
$380
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:25 pm -
Nonstop3h 10m
Sun 9/2011:10 am -
Nonstop2h 59m
Deal found 8/25![United Airlines logo]()
$362
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:10 pm -
1 stop6h 35m
Sun 9/205:00 am -
1 stop5h 20m
Deal found 8/25![Southwest logo]()
$372
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:40 pm -
1 stop6h 04m
Mon 9/286:05 am -
1 stop5h 14m
Deal found 8/25![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 9/109:15 am -
Nonstop2h 50m
Thu 9/109:29 pm -
3 stops40h 46m
Deal found 8/29![Multiple Airlines logo]()
$455
This Southwest deal was found by Cheapflights users on 8/27. 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.
Fri 9/255:40 pm -
1 stop5h 45m
Sun 9/271:10 pm -
2 stops8h 05m
Deal found 8/27![Southwest logo]()
$398
This United Airlines deal was found by Cheapflights users on 8/28. 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.
Thu 10/1512:10 pm -
Nonstop3h 17m
Tue 10/204:00 pm -
1 stop6h 30m
Deal found 8/28![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 8/29. 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.
Wed 11/1111:16 am -
1 stop6h 49m
Sat 11/141:30 pm -
1 stop7h 01m
Deal found 8/29![Delta logo]()
$391
This United Airlines deal was found by Cheapflights users on 8/26. 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 10/14:20 pm -
Nonstop3h 11m
Sun 10/47:00 am -
Nonstop3h 07m
Deal found 8/26![United Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 8/28. 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.
Sat 9/123:20 pm -
Nonstop2h 40m
Wed 9/1610:10 am -
2 stops8h 55m
Deal found 8/28![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 8/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/712:45 pm -
Nonstop3h 00m
Fri 12/115:55 am -
2 stops10h 20m
Deal found 8/30![Southwest logo]()
$422
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:05 am -
1 stop7h 54m
Fri 9/2511:00 am -
Nonstop2h 59m
Deal found 8/25![United Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Tue 12/227:35 am -
Nonstop2h 59m
Sat 12/266:42 pm -
2 stops18h 55m
Deal found 8/28![Allegiant Air logo]()
$629
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:20 pm -
Nonstop3h 11m
Wed 10/149:04 am -
2 stops13h 26m
Deal found 8/25![United Airlines logo]()
$439
This United Airlines deal was found by Cheapflights users on 8/27. 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 11/116:00 am -
1 stop6h 47m
Sat 11/1410:45 am -
2 stops11h 32m
Deal found 8/27![United Airlines logo]()
$444
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 12/211:05 pm -
2 stops28h 45m
Tue 12/2910:24 am -
Nonstop2h 43m
Deal found 8/26![Allegiant Air logo]()
$731
This United Airlines deal was found by Cheapflights users on 8/26. 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.
Wed 9/234:25 pm -
Nonstop3h 10m
Sat 9/267:14 am -
Nonstop3h 07m
Deal found 8/26![United Airlines logo]()
$471
Last-minute flights from Sarasota to ChicagoDiscover last-minute flight deals from Sarasota to Chicago. Data last updated August 30, 2026 and is based on user searches.
Discover last-minute flight deals from Sarasota to Chicago. Data last updated August 30, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/27. 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 9/39:15 am -
Nonstop2h 50m
Sun 9/1311:55 am -
Nonstop2h 40m
Deal found 8/27![Allegiant Air logo]()
$242
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Thu 9/174:25 pm -
Nonstop3h 10m
Tue 9/2211:10 am -
Nonstop2h 59m
Deal found 8/27![United Airlines logo]()
$248
This Southwest deal was found by Cheapflights users on 8/26. 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 9/225:00 pm -
2 stops6h 25m
Tue 9/291:40 pm -
Nonstop2h 35m
Deal found 8/26![Southwest logo]()
$232
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/224:25 pm -
Nonstop3h 10m
Sat 9/267:14 am -
Nonstop3h 07m
Deal found 8/25![United Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 8/27. 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 9/235:55 pm -
Nonstop2h 40m
Mon 9/2812:20 pm -
Nonstop2h 35m
Deal found 8/27![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 8/27. 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 9/246:50 am -
2 stops6h 30m
Fri 9/2512:20 pm -
Nonstop2h 35m
Deal found 8/27![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 8/27. 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 9/244:35 pm -
1 stop5h 25m
Thu 10/16:40 pm -
Nonstop2h 35m
Deal found 8/27![Southwest logo]()
$284
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:20 pm -
Nonstop3h 11m
Fri 10/27:00 am -
Nonstop3h 07m
Deal found 8/25![United Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 8/27. 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.
Fri 9/2511:45 am -
1 stop7h 30m
Mon 9/283:20 pm -
1 stop5h 15m
Deal found 8/27![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 8/27. 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.
Fri 9/256:35 pm -
1 stop6h 24m
Mon 9/286:40 am -
1 stop4h 39m
Deal found 8/27![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 8/26. 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.
Fri 9/255:10 pm -
1 stop6h 35m
Fri 10/29:50 am -
1 stop6h 20m
Deal found 8/26![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/26. 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.
Wed 9/304:20 pm -
Nonstop3h 11m
Sat 10/103:00 pm -
1 stop7h 30m
Deal found 8/26![United Airlines logo]()
$253
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 August 30, 2026.
Search for one-way flight options from Sarasota to Chicago. Find affordable one-way fares based on user searches. Data last updated August 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Thu 12/241:25 pm -
Nonstop2h 59m
Deal found 8/28![Allegiant Air logo]()
$81
This Super.com deal was found by Cheapflights users on 8/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/279:15 am -
Nonstop2h 50m
Deal found 8/30![Allegiant Air logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Thu 9/249:15 am -
Nonstop2h 50m
Deal found 8/28![Allegiant Air logo]()
$83
This Jetabroad deal was found by Cheapflights users on 8/26. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/78:11 am -
Nonstop3h 03m
Deal found 8/26![Allegiant Air logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 10/292:51 pm -
1 stop23h 45m
Deal found 8/29![Allegiant Air logo]()
$107
This Southwest deal was found by Cheapflights users on 8/27. 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.
Mon 10/266:10 am -
Nonstop2h 45m
Deal found 8/27![Southwest logo]()
$109
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Thu 9/174:25 pm -
Nonstop3h 10m
Deal found 8/27![United Airlines logo]()
$109
This Booking.com deal was found by Cheapflights users on 8/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/139:15 am -
Nonstop2h 50m
Deal found 8/29![Allegiant Air logo]()
$110
This Delta deal was found by Cheapflights users on 8/27. 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.
Wed 2/246:45 pm -
1 stop4h 25m
Deal found 8/27![Delta logo]()
$119
This Delta deal was found by Cheapflights users on 8/27. 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 9/286:35 pm -
1 stop6h 24m
Deal found 8/27![Delta logo]()
$119
This Southwest deal was found by Cheapflights users on 8/27. 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.
Fri 9/254:35 pm -
1 stop5h 25m
Deal found 8/27![Southwest logo]()
$129
This Delta deal was found by Cheapflights users on 8/27. 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.
Fri 9/256:35 pm -
1 stop6h 24m
Deal found 8/27![Delta logo]()
$129
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 August 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $232 (Southwest) |
One-way from | $81 (Kiwi.com) |
Popular in | November |
Cheapest in | September |
Average price | $387 |
Good round-trip deal | $297 or less |
Good one-way deal | $185 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 August 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
Quickest round-trip
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Wed 9/23
5:55 pm-7:35 pm
Nonstop2h 40m
Chicago Midway
Mon 9/28
12:20 pm-3:55 pm
Nonstop2h 35m
$237
SarasotaChicago
SRQ Sarasota Bradenton Intl - RFD Chicago Greater Rockford
SRQRFD
Sarasota Bradenton Intl
Thu 10/15
8:01 am-9:51 am
Nonstop2h 50m
Chicago Greater Rockford
Sun 10/18
11:30 am-3:07 pm
Nonstop2h 37m
$246
SarasotaChicago
SRQ Sarasota Bradenton Intl - ORD Chicago O'Hare Intl
SRQORD
Sarasota Bradenton Intl
Mon 12/21
3:32 pm-9:30 pm
1 stop6h 58m
Chicago O'Hare Intl
Tue 12/29
6:40 am-2:27 pm
1 stop6h 47m
$288
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Mon 12/21
7:15 am-9:05 am
Nonstop2h 50m
Chicago Midway
Tue 12/29
9:50 am-6:40 pm
1 stop7h 50m
$290
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Fri 9/25
6:35 pm-10:44 pm
1 stop5h 09m
Chicago Midway
Mon 9/28
6:05 am-12:19 pm
1 stop5h 14m
$298
SarasotaChicago
SRQ Sarasota Bradenton Intl - ORD Chicago O'Hare Intl
SRQORD
Sarasota Bradenton Intl
Fri 12/4
6:28 pm-8:40 pm
Nonstop3h 12m
Chicago O'Hare Intl
Mon 12/7
10:45 am-2:41 pm
Nonstop2h 56m
$317
SarasotaChicago
SRQ Sarasota Bradenton Intl - ORD Chicago O'Hare Intl
SRQORD
Sarasota Bradenton Intl
Fri 10/23
4:20 pm-6:31 pm
Nonstop3h 11m
Chicago O'Hare Intl
Mon 10/26
12:59 pm-11:08 pm
1 stop9h 09m
$327
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Wed 9/30
6:00 am-9:49 am
1 stop4h 49m
Chicago Midway
Fri 10/2
6:05 am-12:19 pm
1 stop5h 14m
$328
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Sat 9/26
5:40 pm-10:44 pm
1 stop6h 04m
Chicago Midway
Mon 9/28
6:05 am-12:19 pm
1 stop5h 14m
$339
SarasotaChicago
SRQ Sarasota Bradenton Intl - ORD Chicago O'Hare Intl
SRQORD
Sarasota Bradenton Intl
Fri 9/18
4:25 pm-6:35 pm
Nonstop3h 10m
Chicago O'Hare Intl
Sun 9/20
11:10 am-3:09 pm
Nonstop2h 59m
$362
Showing 1-10 of 56 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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | 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, September is the cheapest month in which you can book a flight from Sarasota to Chicago (average of $355). Flying from Sarasota to Chicago in January is currently the most expensive (average of $460). 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 August 30, 2026.
It’s typically best to fly out from Sarasota to Chicago in the evening. Doing so could potentially save you 32% 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 $332 and $499 in September.The cheapest round-trip price found within the last 5 days was $232 on Southwest (Sep 22-Sep 29).
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 August 29, 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 August 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
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
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
Lansing
Merrillville
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 August 30, 2026.
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Top 5 airlines flying from Sarasota to Chicago
Discover the top 5 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 August 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$117 | Average$202 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$142 | Average$360 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$239 | Average$403 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$240 | Average$411 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$432 | FlexibilityNo cancel fee | On-time63% |