$109+ Cheap flights from Chicago (CHI) to Sarasota (SRQ)
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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SRQ
Sep 29 — Oct 61
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Sarasota 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 Chicago to Sarasota Bradenton Intl are usually found in January or September, booked 28 days in advance, depart on a Sunday or Thursday and return on a Saturday
Cheap flight deals from Chicago to Sarasota
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Cheapest flights from Chicago to SarasotaExplore the most affordable flight options available from Chicago to Sarasota. 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 Chicago to Sarasota. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 30, 2026.
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.
Sat 12/53:55 pm -
1 stop4h 28m
Sat 12/127:08 am -
1 stop6h 12m
Deal found 8/27![Delta logo]()
$237
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 11/411:39 am -
1 stop7h 17m
Mon 11/94:30 pm -
1 stop7h 24m
Deal found 8/27![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.
Fri 10/26:40 pm -
Nonstop2h 35m
Thu 10/86:20 pm -
2 stops5h 55m
Deal found 8/27![Southwest logo]()
$242
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 10/67:00 am -
Nonstop3h 07m
Wed 10/214:20 pm -
Nonstop3h 11m
Deal found 8/25![United Airlines logo]()
$243
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 12/48:04 am -
1 stop6h 22m
Tue 12/85:37 pm -
1 stop7h 15m
Deal found 8/27![Delta 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 12/45:14 pm -
1 stop6h 16m
Mon 12/74:38 pm -
1 stop7h 17m
Deal found 8/27![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.
Tue 9/2211:10 am -
Nonstop2h 59m
Tue 9/294:20 pm -
Nonstop3h 11m
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.
Thu 11/127:50 am -
2 stops11h 15m
Mon 11/166:45 pm -
1 stop4h 55m
Deal found 8/27![Southwest logo]()
$248
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 11/311:44 am -
Nonstop2h 54m
Wed 11/116:00 am -
1 stop8h 09m
Deal found 8/25![United Airlines logo]()
$249
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.
Tue 10/67:00 am -
Nonstop3h 07m
Wed 10/146:20 am -
1 stop7h 34m
Deal found 8/27![United Airlines logo]()
$253
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 11/97:50 am -
2 stops11h 15m
Sat 11/149:40 am -
2 stops8h 40m
Deal found 8/27![Southwest logo]()
$253
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 12/411:35 am -
1 stop4h 39m
Fri 12/116:24 pm -
1 stop6h 28m
Deal found 8/27![Delta logo]()
$257
Best flights from Chicago to SarasotaDiscover carefully curated flight deals from Chicago to Sarasota 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 Chicago to Sarasota that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 30, 2026.
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.
Wed 1/65:25 pm -
1 stop6h 02m
Sat 1/164:55 pm -
1 stop6h 15m
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.
Mon 1/1812:45 pm -
Nonstop2h 35m
Tue 1/1912:50 pm -
Nonstop2h 50m
Deal found 8/27![Southwest logo]()
$274
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.
Thu 9/1011:10 am -
Nonstop2h 59m
Sat 9/266:20 am -
1 stop9h 25m
Deal found 8/25![United Airlines logo]()
$384
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 12/45:14 pm -
1 stop6h 16m
Mon 12/74:38 pm -
1 stop7h 17m
Deal found 8/25![Delta 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.
Mon 9/215:30 am -
1 stop5h 49m
Tue 10/65:35 pm -
1 stop7h 22m
Deal found 8/27![Delta logo]()
$328
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.
Mon 10/1911:05 am -
2 stops7h 50m
Sat 10/247:10 am -
2 stops7h 45m
Deal found 8/25![Southwest logo]()
$361
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 11/1212:45 pm -
2 stops9h 30m
Sun 11/155:50 pm -
2 stops7h 15m
Deal found 8/27![Southwest logo]()
$366
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.
Mon 9/1411:10 am -
Nonstop2h 59m
Fri 9/184:25 pm -
Nonstop3h 10m
Deal found 8/25![United Airlines logo]()
$406
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.
Fri 11/135:30 am -
1 stop6h 43m
Sun 11/156:25 pm -
1 stop6h 29m
Deal found 8/26![Delta logo]()
$349
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.
Mon 1/412:50 pm -
2 stops9h 35m
Thu 1/1411:40 am -
1 stop7h 50m
Deal found 8/25![Southwest logo]()
$391
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 9/411:10 am -
Nonstop3h 00m
Tue 9/296:20 am -
1 stop7h 34m
Deal found 8/25![United Airlines logo]()
$442
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.
Sun 9/135:30 am -
1 stop5h 49m
Sat 9/195:40 pm -
1 stop7h 19m
Deal found 8/27![Delta logo]()
$372
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:50 pm -
2 stops6h 00m
Tue 10/611:40 am -
1 stop6h 15m
Deal found 8/29![Southwest logo]()
$396
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 10/178:40 am -
1 stop5h 00m
Tue 10/207:15 am -
2 stops9h 15m
Deal found 8/28![Southwest logo]()
$396
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 9/411:10 am -
Nonstop3h 00m
Sun 9/66:05 am -
1 stop6h 54m
Deal found 8/25![United Airlines logo]()
$497
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:08 pm -
1 stop5h 19m
Mon 10/261:21 pm -
1 stop6h 50m
Deal found 8/28![Delta logo]()
$427
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 12/41:15 pm -
2 stops6h 30m
Mon 12/77:05 am -
2 stops6h 50m
Deal found 8/27![Southwest logo]()
$406
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:00 am -
Nonstop2h 59m
Mon 10/266:00 am -
1 stop8h 59m
Deal found 8/29![United Airlines logo]()
$525
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.
Thu 9/1712:20 pm -
Nonstop2h 35m
Mon 9/2112:05 pm -
Nonstop2h 40m
Deal found 8/26![Southwest logo]()
$409
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:00 am -
Nonstop3h 07m
Sun 10/46:20 am -
1 stop6h 40m
Deal found 8/29![United Airlines logo]()
$525
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:05 am -
2 stops7h 50m
Wed 10/711:40 am -
2 stops6h 30m
Deal found 8/29![Southwest logo]()
$419
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.
Thu 9/35:30 am -
1 stop5h 53m
Mon 9/76:00 am -
1 stop5h 13m
Deal found 8/25![Delta logo]()
$507
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 10/1611:00 am -
Nonstop2h 59m
Fri 10/164:20 pm -
Nonstop3h 11m
Deal found 8/25![United Airlines logo]()
$548
Last-minute flights from Chicago to SarasotaDiscover last-minute flight deals from Chicago to Sarasota. Data last updated August 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Sarasota. Data last updated August 30, 2026 and is based on user searches.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:28 pm -
2 stops42h 47m
Fri 10/26:24 pm -
1 stop25h 03m
Deal found 8/25![Multiple Airlines logo]()
$283
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.
Thu 9/1712:20 pm -
Nonstop2h 35m
Thu 9/245:10 pm -
1 stop6h 35m
Deal found 8/26![Southwest logo]()
$284
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 9/1812:20 pm -
Nonstop2h 35m
Thu 9/245:10 pm -
1 stop6h 35m
Deal found 8/25![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.
Sat 9/193:40 pm -
1 stop6h 20m
Sat 9/265:40 pm -
1 stop7h 19m
Deal found 8/27![Delta logo]()
$288
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.
Tue 9/225:30 am -
1 stop5h 49m
Tue 9/295:40 pm -
1 stop7h 19m
Deal found 8/27![Delta 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.
Tue 9/225:30 am -
1 stop5h 49m
Fri 10/26:35 pm -
1 stop6h 24m
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.
Tue 9/2211:10 am -
Nonstop2h 59m
Tue 9/294:20 pm -
Nonstop3h 11m
Deal found 8/27![United Airlines logo]()
$248
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 9/2211:10 am -
Nonstop2h 59m
Sat 9/264:20 pm -
Nonstop3h 11m
Deal found 8/25![United Airlines logo]()
$274
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 9/231:30 pm -
1 stop8h 45m
Sat 10/34:20 pm -
Nonstop3h 11m
Deal found 8/25![United Airlines logo]()
$258
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 9/286:05 am -
1 stop5h 14m
Mon 9/286:35 pm -
1 stop5h 09m
Deal found 8/27![Delta logo]()
$288
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 9/292:40 pm -
1 stop4h 25m
Tue 10/137:15 am -
2 stops8h 25m
Deal found 8/26![Southwest logo]()
$242
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.
Wed 9/301:40 pm -
Nonstop2h 35m
Sat 10/32:05 pm -
1 stop5h 00m
Deal found 8/26![Southwest logo]()
$237
One-way flights from Chicago to SarasotaSearch for one-way flight options from Chicago to Sarasota. Find affordable one-way fares based on user searches. Data last updated August 30, 2026.
Search for one-way flight options from Chicago to Sarasota. Find affordable one-way fares based on user searches. Data last updated August 30, 2026.
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.
Sat 9/267:14 am -
Nonstop3h 07m
Deal found 8/27![United Airlines logo]()
$109
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.
Sat 9/267:50 am -
Nonstop2h 40m
Deal found 8/27![Southwest logo]()
$109
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:27 am -
1 stop5h 49m
Deal found 8/28![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 10/266:04 am -
1 stop5h 12m
Deal found 8/27![Delta logo]()
$119
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.
Wed 9/1612:50 pm -
2 stops6h 00m
Deal found 8/26![Southwest logo]()
$124
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 11/239:29 am -
1 stop11h 03m
Deal found 8/26![Allegiant Air logo]()
$128
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:40 pm -
1 stop6h 38m
Deal found 8/28![Delta logo]()
$129
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 10/235:09 pm -
1 stop6h 18m
Deal found 8/25![Delta logo]()
$129
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 10/302:50 pm -
2 stops7h 05m
Deal found 8/26![Southwest logo]()
$134
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.
Tue 9/2211:10 am -
Nonstop2h 59m
Deal found 8/27![United Airlines logo]()
$145
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.
Mon 9/283:00 pm -
1 stop7h 30m
Deal found 8/26![United Airlines logo]()
$150
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1810:59 am -
1 stop6h 42m
Deal found 8/25![JetBlue logo]()
$162
Find flight deals from Chicago to Sarasota
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Sarasota (SRQ). 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 | $237 (Delta) |
One-way from | $109 (United Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $405 |
Good round-trip deal | $158 or less |
Good one-way deal | $143 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Sarasota 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 Chicago to Sarasota that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSarasota
MDW Chicago Midway - SRQ Sarasota Bradenton Intl
MDWSRQ
Chicago Midway
Wed 1/6
5:25 pm-12:27 am
1 stop6h 02m
Sarasota Bradenton Intl
Sat 1/16
4:55 pm-10:10 pm
1 stop6h 15m
$237
ChicagoSarasota
MDW Chicago Midway - SRQ Sarasota Bradenton Intl
MDWSRQ
Chicago Midway
Fri 12/4
5:14 pm-12:30 am
1 stop6h 16m
Sarasota Bradenton Intl
Mon 12/7
4:38 pm-10:55 pm
1 stop7h 17m
$247
ChicagoSarasota
MDW Chicago Midway - SRQ Sarasota Bradenton Intl
MDWSRQ
Chicago Midway
Mon 1/18
12:45 pm-4:20 pm
Nonstop2h 35m
Sarasota Bradenton Intl
Tue 1/19
12:50 pm-2:40 pm
Nonstop2h 50m
$274
ChicagoSarasota
ORD Chicago O'Hare Intl - SRQ Sarasota Bradenton Intl
ORDSRQ
Chicago O'Hare Intl
Mon 9/21
5:30 am-12:19 pm
1 stop5h 49m
Sarasota Bradenton Intl
Tue 10/6
5:35 pm-11:57 pm
1 stop7h 22m
$328
ChicagoSarasota
ORD Chicago O'Hare Intl - SRQ Sarasota Bradenton Intl
ORDSRQ
Chicago O'Hare Intl
Fri 11/13
5:30 am-1:13 pm
1 stop6h 43m
Sarasota Bradenton Intl
Sun 11/15
6:25 pm-11:54 pm
1 stop6h 29m
$349
ChicagoSarasota
MDW Chicago Midway - SRQ Sarasota Bradenton Intl
MDWSRQ
Chicago Midway
Mon 10/19
11:05 am-7:55 pm
2 stops7h 50m
Sarasota Bradenton Intl
Sat 10/24
7:10 am-1:55 pm
2 stops7h 45m
$361
ChicagoSarasota
MDW Chicago Midway - SRQ Sarasota Bradenton Intl
MDWSRQ
Chicago Midway
Thu 11/12
12:45 pm-11:15 pm
2 stops9h 30m
Sarasota Bradenton Intl
Sun 11/15
5:50 pm-12:05 am
2 stops7h 15m
$366
ChicagoSarasota
ORD Chicago O'Hare Intl - SRQ Sarasota Bradenton Intl
ORDSRQ
Chicago O'Hare Intl
Sun 9/13
5:30 am-12:19 pm
1 stop5h 49m
Sarasota Bradenton Intl
Sat 9/19
5:40 pm-11:59 pm
1 stop7h 19m
$372
ChicagoSarasota
ORD Chicago O'Hare Intl - SRQ Sarasota Bradenton Intl
ORDSRQ
Chicago O'Hare Intl
Thu 9/10
11:10 am-3:09 pm
Nonstop2h 59m
Sarasota Bradenton Intl
Sat 9/26
6:20 am-2:45 pm
1 stop9h 25m
$384
ChicagoSarasota
MDW Chicago Midway - SRQ Sarasota Bradenton Intl
MDWSRQ
Chicago Midway
Mon 1/4
12:50 pm-11:25 pm
2 stops9h 35m
Sarasota Bradenton Intl
Thu 1/14
11:40 am-6:30 pm
1 stop7h 50m
$391
Showing 1-10 of 46 resultsSorted by cheapest first
Compare providers for flights from Chicago to Sarasota
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 Chicago to Sarasota 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 Chicago-Sarasota flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Sarasota flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Sarasota flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Sarasota 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 Chicago-Sarasota 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 Chicago to Sarasota
Have a flexible travel schedule? Discover the best time to fly to Sarasota from Chicago with our price prediction graph.
CHI-SRQ
ORD-SRQ
MDW-SRQ
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 Chicago to Sarasota
CHI-SRQ
ORD-SRQ
MDW-SRQ
What is the cheapest month to book a flight from Chicago to Sarasota?
Currently, September is the cheapest month in which you can book a flight from Chicago to Sarasota (average of $296). Flying from Chicago to Sarasota in March is currently the most expensive (average of $444). 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 CHI to SRQ?
Find hourly flight availability from Chicago to Sarasota. 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 optimal to fly from Chicago to Sarasota in the morning. By choosing this option you can save up to 33% on the cost of your flight, compared to a flight in the evening.
How much does it cost to fly round-trip from Chicago to Sarasota?
Airfare is below average for this route at the moment.
Chicago to Sarasota flights typically cost between $320 and $430 in January.The cheapest round-trip price found within the last 5 days was $237 on Delta (Jan 23-Feb 13).
How far ahead should I book a flight from Chicago to Sarasota?
To ensure you get the cheapest price possible for a flight from Chicago to Sarasota, you should look to book at least 24 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Chicago to Sarasota?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Sarasota. Price data was last updated on August 29, 2026.
Travelers seeking maximum savings on their Chicago to Sarasota flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago to Sarasota 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 Chicago to Sarasota trip
Our travel experts
Reviews of airlines servicing Sarasota
Get insights into the airlines that provide service to Sarasota. 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 Sarasota. Reviews last updated August 30, 2026.
Read through reviews of airlines operating flights from Chicago to Sarasota, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Sarasota. 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 Sarasota?
Book flights to Sarasota if you plan to visit one of these locationsVenice
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Chicago and Sarasota flights
Browse other Chicago and Sarasota flight options. Last updated on August 30, 2026.
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Top 6 airlines flying from Chicago to Sarasota
Discover the top 6 airlines that operate flights from Chicago to Sarasota. 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$58 | Average$213 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$113 | Average$220 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$152 | Average$352 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$217 | Average$396 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$279 | Average$442 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$280 | Average$414 | FlexibilityNo cancel fee | On-time63% |