$125+ Cheap flights from Chicago (CHI) to Siesta Key, FL
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 3/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TPA
Mar 15 — Mar 221
1 adult, Economy
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Find cheap flights from Chicago to Siesta Key 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 Siesta Key are usually found in April or July, booked 17 days in advance, depart on a Wednesday or Thursday and return on a Friday
Cheap flight deals from Chicago to Siesta Key
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Best
Last-minute
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Cheapest flights from Chicago to Siesta KeyExplore the most affordable flight options available from Chicago to Siesta Key. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.
Explore the most affordable flight options available from Chicago to Siesta Key. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/231:12 pm
ORD
- SRQ
1 stop26h 25m
Multiple Airlines
Thu 4/309:30 am
SRQ
- ORD
1 stop9h 21m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:15 pm
ORD
- SRQ
2 stops22h 51m
Multiple Airlines
Sun 5/39:30 am
SRQ
- ORD
1 stop9h 21m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2812:06 pm
ORD
- SRQ
2 stops24h 33m
Multiple Airlines
Thu 3/51:27 pm
SRQ
- ORD
1 stop29h 28m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$304
This CheapOair deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/197:20 am
ORD
- SRQ
1 stop26h 37m
Multiple Airlines
Fri 4/249:07 am
SRQ
- ORD
1 stop12h 01m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/233:52 pm
ORD
- SRQ
2 stops23h 45m
Multiple Airlines
Sun 5/39:30 am
SRQ
- ORD
1 stop9h 21m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/263:15 pm
ORD
- SRQ
2 stops24h 22m
Multiple Airlines
Sun 5/39:30 am
SRQ
- ORD
1 stop9h 21m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/226:04 am
ORD
- SRQ
1 stop9h 45m
Delta
Tue 5/511:05 am
SRQ
- ORD
1 stop10h 31m
Delta
Deal found 2/9![Delta logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:10 pm
ORD
- SRQ
2 stops40h 48m
Multiple Airlines
Mon 4/137:05 am
SRQ
- ORD
1 stop12h 25m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 4/275:01 am
ORD
- SRQ
2 stops9h 31m
Multiple Airlines
Thu 5/79:30 am
SRQ
- ORD
1 stop9h 21m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$317
This CheapOair deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:41 am
ORD
- SRQ
2 stops30h 34m
Multiple Airlines
Mon 5/119:07 am
SRQ
- ORD
1 stop12h 01m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/104:14 pm
ORD
- SRQ
Nonstop2h 53m
United Airlines
Wed 3/1812:23 pm
SRQ
- ORD
Nonstop3h 19m
United Airlines
Deal found 2/13![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/107:40 am
MDW
- SRQ
Nonstop2h 40m
Southwest
Tue 3/246:40 am
SRQ
- MDW
Nonstop2h 50m
Southwest
Deal found 2/12![Southwest logo]()
$319
Best flights from Chicago to Siesta KeyDiscover carefully curated flight deals from Chicago to Siesta Key that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 13, 2026.
Discover carefully curated flight deals from Chicago to Siesta Key that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 13, 2026.
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/286:04 am
ORD
- SRQ
1 stop9h 45m
Delta
Tue 5/511:05 am
SRQ
- ORD
1 stop12h 10m
Delta
Deal found 2/9![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/1211:15 am
ORD
- SRQ
Nonstop3h 03m
United Airlines
Wed 5/209:05 am
SRQ
- ORD
Nonstop3h 16m
United Airlines
Deal found 2/10![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 5/131:30 pm
MDW
- SRQ
Nonstop2h 35m
Southwest
Tue 5/195:50 pm
SRQ
- MDW
Nonstop2h 45m
Southwest
Deal found 2/13![Southwest logo]()
$321
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/256:04 am
ORD
- SRQ
1 stop9h 45m
Delta
Tue 5/511:05 am
SRQ
- ORD
1 stop12h 10m
Delta
Deal found 2/9![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/1011:04 am
ORD
- SRQ
Nonstop3h 00m
United Airlines
Wed 3/187:15 am
SRQ
- ORD
Nonstop3h 19m
United Airlines
Deal found 2/9![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/109:20 am
MDW
- SRQ
1 stop5h 20m
Southwest
Tue 3/246:40 am
SRQ
- MDW
Nonstop2h 50m
Southwest
Deal found 2/12![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/226:04 am
ORD
- SRQ
1 stop9h 45m
Delta
Tue 5/511:05 am
SRQ
- ORD
1 stop10h 31m
Delta
Deal found 2/9![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/257:10 am
ORD
- SRQ
Nonstop3h 01m
United Airlines
Tue 4/284:15 pm
SRQ
- ORD
Nonstop3h 13m
United Airlines
Deal found 2/11![United Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 4/2210:15 am
MDW
- SRQ
1 stop6h 10m
Southwest
Wed 4/295:50 pm
SRQ
- MDW
Nonstop2h 45m
Southwest
Deal found 2/12![Southwest logo]()
$329
This United Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 4/72:30 pm
ORD
- SRQ
1 stop8h 29m
United Airlines
Tue 4/149:20 am
SRQ
- ORD
Nonstop3h 13m
United Airlines
Deal found 2/12![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/177:00 pm
MDW
- SRQ
Nonstop2h 35m
Southwest
Wed 3/257:00 am
SRQ
- MDW
1 stop4h 25m
Southwest
Deal found 2/11![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/276:04 am
ORD
- SRQ
1 stop9h 45m
Delta
Wed 4/2912:45 pm
SRQ
- ORD
1 stop4h 57m
Delta
Deal found 2/9![Delta logo]()
$331
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/155:48 am
ORD
- SRQ
1 stop8h 59m
United Airlines
Sat 4/184:15 pm
SRQ
- ORD
Nonstop3h 13m
United Airlines
Deal found 2/10![United Airlines logo]()
$330
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/131:30 pm
MDW
- SRQ
Nonstop2h 35m
Southwest
Mon 5/187:05 am
SRQ
- MDW
Nonstop2h 50m
Southwest
Deal found 2/11![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/287:10 am
ORD
- SRQ
1 stop10h 01m
Delta
Sat 5/212:55 pm
SRQ
- ORD
1 stop7h 28m
Delta
Deal found 2/9![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/81:30 pm
MDW
- SRQ
Nonstop2h 35m
Southwest
Tue 4/145:50 pm
SRQ
- MDW
Nonstop2h 45m
Southwest
Deal found 2/11![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/276:04 am
ORD
- SRQ
1 stop9h 45m
Delta
Sat 5/26:25 pm
SRQ
- ORD
1 stop6h 34m
Delta
Deal found 2/9![Delta logo]()
$332
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/74:14 pm
ORD
- SRQ
Nonstop2h 53m
United Airlines
Wed 3/116:04 am
SRQ
- ORD
1 stop8h 11m
United Airlines
Deal found 2/9![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/17:00 pm
MDW
- SRQ
Nonstop2h 35m
Southwest
Wed 4/89:20 am
SRQ
- MDW
2 stops8h 45m
Southwest
Deal found 2/10![Southwest logo]()
$334
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/216:00 am
MDW
- SRQ
1 stop7h 19m
Delta
Tue 4/286:00 am
SRQ
- MDW
1 stop4h 56m
Delta
Deal found 2/10![Delta logo]()
$339
Last-minute flights from Chicago to Siesta KeyDiscover last-minute flight deals from Chicago to Siesta Key. Data last updated February 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Siesta Key. Data last updated February 13, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2310:15 am
ORD
- SRQ
1 stop8h 02m
Multiple Airlines
Thu 2/265:40 pm
SRQ
- ORD
2 stops16h 30m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2812:06 pm
ORD
- SRQ
2 stops24h 33m
Multiple Airlines
Thu 3/51:27 pm
SRQ
- ORD
1 stop29h 28m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/285:20 pm
ORD
- SRQ
1 stop16h 11m
Delta
Fri 3/67:10 pm
SRQ
- ORD
1 stop13h 48m
Delta
Deal found 2/12![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/77:05 pm
MDW
- SRQ
Nonstop2h 35m
Southwest
Wed 3/116:40 am
SRQ
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$331
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/74:14 pm
ORD
- SRQ
Nonstop2h 53m
United Airlines
Wed 3/116:04 am
SRQ
- ORD
1 stop8h 11m
United Airlines
Deal found 2/9![United Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/104:14 pm
ORD
- SRQ
Nonstop2h 53m
United Airlines
Wed 3/1812:23 pm
SRQ
- ORD
Nonstop3h 19m
United Airlines
Deal found 2/13![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/107:40 am
MDW
- SRQ
Nonstop2h 40m
Southwest
Tue 3/246:40 am
SRQ
- MDW
Nonstop2h 50m
Southwest
Deal found 2/12![Southwest logo]()
$319
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/103:40 pm
ORD
- SRQ
1 stop7h 19m
United Airlines
Tue 3/177:15 am
SRQ
- ORD
Nonstop3h 19m
United Airlines
Deal found 2/13![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/108:00 am
ORD
- SRQ
Nonstop2h 51m
American Airlines
Mon 3/1612:48 pm
SRQ
- ORD
Nonstop3h 12m
American Airlines
Deal found 2/13![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/107:10 am
ORD
- SRQ
1 stop10h 52m
Delta
Tue 3/176:00 am
SRQ
- ORD
1 stop5h 00m
Delta
Deal found 2/9![Delta logo]()
$336
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/259:35 am
ORD
- SRQ
1 stop8h 27m
Delta
Wed 4/16:00 am
SRQ
- ORD
1 stop4h 59m
Delta
Deal found 2/13![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/2510:00 am
MDW
- SRQ
1 stop6h 15m
Southwest
Wed 4/86:05 pm
SRQ
- MDW
1 stop4h 20m
Southwest
Deal found 2/11![Southwest logo]()
$339
One-way flights from Chicago to Siesta KeySearch for one-way flight options from Chicago to Siesta Key. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
Search for one-way flight options from Chicago to Siesta Key. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
This Priceline deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2210:12 pm
ORD
- SRQ
1 stop9h 04m
Frontier
Deal found 2/11![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/307:30 am
MDW
- SRQ
2 stops34h 26m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:14 am
MDW
- SRQ
2 stops28h 52m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/301:12 pm
ORD
- SRQ
1 stop28h 44m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/237:30 am
MDW
- SRQ
2 stops32h 07m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:25 am
MDW
- SRQ
2 stops35h 38m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2812:06 pm
ORD
- SRQ
2 stops24h 33m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/162:20 pm
MDW
- SRQ
2 stops24h 42m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/39:14 am
MDW
- SRQ
2 stops32h 42m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/68:16 pm
ORD
- SRQ
2 stops37h 29m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/96:05 am
MDW
- SRQ
2 stops15h 46m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/316:10 pm
ORD
- SRQ
2 stops39h 35m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$148
Find flight deals from Chicago to Siesta Key
Keep the following information in mind while searching for Chicago to Siesta Key flight deals. Data was last updated February 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $301 (Kiwi.com) |
One-way from | $125 (Priceline) |
Popular in | December |
Cheapest in | April |
Average price | $376 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Siesta Key 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 2,558,603 searches. Data last updated February 13, 2026.
Use the filters below to find and compare flights from Chicago to Siesta Key that are best for you.
Fly from
Chicago
Fly to
Siesta Key
Route
Depart
Return
Price
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Tue 4/28
6:04 am-4:49 pm
1 stop9h 45m
Sarasota Bradenton Intl
Tue 5/5
11:05 am-10:15 pm
1 stop12h 10m
$313
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Sat 4/25
6:04 am-4:49 pm
1 stop9h 45m
Sarasota Bradenton Intl
Tue 5/5
11:05 am-10:15 pm
1 stop12h 10m
$313
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Wed 4/22
6:04 am-4:49 pm
1 stop9h 45m
Sarasota Bradenton Intl
Tue 5/5
11:05 am-8:36 pm
1 stop10h 31m
$313
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Tue 5/12
11:15 am-3:18 pm
Nonstop3h 03m
Sarasota Bradenton Intl
Wed 5/20
9:05 am-11:21 am
Nonstop3h 16m
$319
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Tue 3/10
11:04 am-3:04 pm
Nonstop3h 00m
Sarasota Bradenton Intl
Wed 3/18
7:15 am-9:34 am
Nonstop3h 19m
$319
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Sat 4/25
7:10 am-11:11 am
Nonstop3h 01m
Sarasota Bradenton Intl
Tue 4/28
4:15 pm-6:28 pm
Nonstop3h 13m
$320
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Wed 5/13
1:30 pm-5:05 pm
Nonstop2h 35m
Sarasota Bradenton Intl
Tue 5/19
5:50 pm-7:35 pm
Nonstop2h 45m
$321
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Tue 3/10
9:20 am-3:40 pm
1 stop5h 20m
Sarasota Bradenton Intl
Tue 3/24
6:40 am-8:30 am
Nonstop2h 50m
$329
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Wed 4/22
10:15 am-5:25 pm
1 stop6h 10m
Sarasota Bradenton Intl
Wed 4/29
5:50 pm-7:35 pm
Nonstop2h 45m
$329
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Tue 4/7
2:30 pm-11:59 pm
1 stop8h 29m
Sarasota Bradenton Intl
Tue 4/14
9:20 am-11:33 am
Nonstop3h 13m
$329
Showing 1-10 of 42 results
Best time to book a flight from Chicago to Siesta Key
Have a flexible travel schedule? Discover the best time to fly to Siesta Key from Chicago with our price prediction graph.
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 Siesta Key
CHI-S1E
ORD-SRQ
MDW-SRQ
How far ahead should I book a flight from Chicago to Siesta Key?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Siesta Key. Price data was last updated on February 6, 2026.
Booking 17 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Siesta Key. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago to Siesta Key?
Currently, March is the cheapest month in which you can book a flight from Chicago to Siesta Key (average of $37). Flying from Chicago to Siesta Key in December is currently the most expensive (average of $102). 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 S1E?
Find hourly flight availability from Chicago to Siesta Key. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 13, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Siesta Key in the afternoon. If you’re flexible enough to do this you can expect to save up to 16% on your trip compared to booking a flight in the evening.
What is the cheapest day to fly from Chicago to Siesta Key?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Siesta Key. Price data was last updated on February 7, 2026.
Travelers seeking maximum savings on their Chicago to Siesta Key flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Siesta Key
Explore weekly flight availability from Chicago to Siesta Key. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 13, 2026.
The most flights from CHI to S1E are scheduled on a Thursday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 on average).
How much does it cost to fly round-trip from Chicago to Siesta Key?
Reviews of airlines servicing Siesta Key
Get insights into the airlines that provide service to Siesta Key. 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 Siesta Key. Reviews last updated February 13, 2026.
Read through reviews of airlines operating flights from Chicago to Siesta Key, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
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 Siesta Key. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Siesta Key
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Complete your trip
Complete your trip to Siesta Key by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Siesta Key by cabin class
Find flights from Chicago to Siesta Key, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Siesta Key flights
Browse other Chicago and Siesta Key flight options. Last updated on February 13, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on February 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 8 airlines flying from Chicago to Siesta Key
Discover the top 8 airlines that operate flights from Chicago to Siesta Key. 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 2,558,603 searches. Data last updated February 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$27 | Average$166 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$61 | Average$188 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$82 | Average$189 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$95 | Average$252 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$129 | Average$360 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$154 | Average$340 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$156 | Average$330 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$358 | FlexibilityNo cancel fee | On-time63% |