$98+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TPA
Jun 17 — Jun 241
Round-trip
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 January or September, booked 42 days in advance, depart on a Thursday or Sunday and return on a Saturday
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 May 18, 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 May 18, 2026.
This Southwest deal was found by Cheapflights users on 5/13. 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.
Tue 9/81:40 pm
MDW
- SRQ
Nonstop2h 35m
Southwest
Sat 9/123:20 pm
SRQ
- MDW
Nonstop2h 40m
Southwest
Deal found 5/13![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/165:30 am
ORD
- SRQ
1 stop5h 15m
Delta
Tue 6/236:23 pm
SRQ
- ORD
1 stop6h 36m
Delta
Deal found 5/14![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 5/13. 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.
Tue 6/1612:50 pm
MDW
- SRQ
1 stop5h 02m
Delta
Tue 6/236:00 am
SRQ
- MDW
1 stop5h 09m
Delta
Deal found 5/13![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 5/13. 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.
Sat 10/38:15 am
MDW
- SRQ
1 stop5h 00m
Southwest
Wed 10/712:35 pm
SRQ
- MDW
Nonstop2h 45m
Southwest
Deal found 5/13![Southwest logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Sun 5/242:47 pm
MDW
- SRQ
1 stop25h 09m
Allegiant Air
Sun 5/318:32 pm
SRQ
- MDW
1 stop19h 20m
Allegiant Air
Deal found 5/13![Allegiant Air logo]()
$261
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/1611:50 am
MDW
- SRQ
1 stop8h 25m
Southwest
Tue 6/233:50 pm
SRQ
- MDW
1 stop4h 15m
Southwest
Deal found 5/16![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 9/2112:25 pm
MDW
- SRQ
Nonstop2h 35m
Southwest
Tue 10/65:50 pm
SRQ
- MDW
1 stop5h 25m
Southwest
Deal found 5/16![Southwest logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/132:49 pm
MDW
- SRQ
1 stop25h 06m
Multiple Airlines
Fri 8/212:21 pm
SRQ
- MDW
2 stops32h 50m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 5/282:47 pm
MDW
- SRQ
1 stop25h 14m
Allegiant Air
Thu 6/45:26 pm
SRQ
- MDW
1 stop22h 22m
Allegiant Air
Deal found 5/13![Allegiant Air logo]()
$265
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/3011:25 am
MDW
- SRQ
2 stops8h 50m
Southwest
Tue 7/76:15 am
SRQ
- MDW
2 stops7h 10m
Southwest
Deal found 5/17![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 8/611:10 am
ORD
- SRQ
Nonstop3h 02m
United Airlines
Mon 8/104:30 pm
SRQ
- ORD
Nonstop3h 16m
United Airlines
Deal found 5/15![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/227:50 am
MDW
- SRQ
Nonstop2h 40m
Southwest
Sat 8/223:20 pm
SRQ
- MDW
Nonstop2h 40m
Southwest
Deal found 5/14![Southwest logo]()
$269
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 May 18, 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 May 18, 2026.
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 10/76:05 am
MDW
- SRQ
1 stop4h 50m
Southwest
Mon 10/126:35 am
SRQ
- MDW
Nonstop2h 40m
Southwest
Deal found 5/17![Southwest logo]()
$263
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 5/286:06 pm
ORD
- SRQ
1 stop5h 12m
Delta
Tue 6/96:22 pm
SRQ
- ORD
1 stop6h 37m
Delta
Deal found 5/15![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 5/282:21 pm
ORD
- SRQ
1 stop7h 54m
United Airlines
Wed 6/34:25 pm
SRQ
- ORD
Nonstop3h 16m
United Airlines
Deal found 5/17![United Airlines logo]()
$396
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 9/213:10 pm
MDW
- SRQ
2 stops5h 40m
Southwest
Tue 10/62:25 pm
SRQ
- MDW
2 stops8h 25m
Southwest
Deal found 5/16![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 5/13. 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.
Sat 7/256:00 am
MDW
- SRQ
1 stop4h 44m
Delta
Wed 7/296:22 pm
SRQ
- MDW
1 stop4h 53m
Delta
Deal found 5/13![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 5/13. 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.
Mon 6/85:05 pm
MDW
- SRQ
1 stop4h 35m
Southwest
Tue 6/97:05 am
SRQ
- MDW
Nonstop2h 40m
Southwest
Deal found 5/13![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 7/56:00 am
MDW
- SRQ
1 stop4h 45m
Delta
Tue 7/147:04 am
SRQ
- MDW
1 stop5h 52m
Delta
Deal found 5/15![Delta logo]()
$334
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/262:10 pm
MDW
- SRQ
Nonstop2h 40m
Southwest
Tue 6/307:05 am
SRQ
- MDW
Nonstop2h 40m
Southwest
Deal found 5/17![Southwest logo]()
$314
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/811:10 am
ORD
- SRQ
Nonstop3h 02m
United Airlines
Mon 7/134:30 pm
SRQ
- ORD
Nonstop3h 16m
United Airlines
Deal found 5/17![United Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 5/13. 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 11/410:35 am
MDW
- SRQ
1 stop4h 10m
Delta
Tue 11/104:55 pm
SRQ
- MDW
1 stop5h 50m
Delta
Deal found 5/13![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 5/13. 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.
Tue 6/96:00 am
MDW
- SRQ
1 stop4h 45m
Delta
Tue 6/166:22 pm
SRQ
- MDW
1 stop4h 55m
Delta
Deal found 5/13![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/179:48 am
ORD
- SRQ
1 stop6h 29m
Delta
Sun 6/216:00 am
SRQ
- ORD
1 stop5h 13m
Delta
Deal found 5/16![Delta logo]()
$342
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Fri 6/2611:10 am
ORD
- SRQ
Nonstop3h 02m
United Airlines
Tue 7/74:30 pm
SRQ
- ORD
Nonstop3h 16m
United Airlines
Deal found 5/13![United Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/136:05 am
MDW
- SRQ
1 stop5h 18m
Delta
Sun 8/166:00 am
SRQ
- MDW
1 stop4h 59m
Delta
Deal found 5/17![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/1811:17 am
ORD
- SRQ
Nonstop3h 02m
United Airlines
Thu 6/254:30 pm
SRQ
- ORD
Nonstop3h 16m
United Airlines
Deal found 5/17![United Airlines logo]()
$481
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1910:35 am
ORD
- SRQ
Nonstop2h 44m
United Airlines
Tue 10/206:05 am
SRQ
- ORD
1 stop7h 01m
United Airlines
Deal found 5/14![United Airlines logo]()
$488
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/2611:23 am
ORD
- SRQ
1 stop4h 54m
Delta
Tue 6/3012:50 pm
SRQ
- ORD
1 stop5h 14m
Delta
Deal found 5/17![Delta logo]()
$375
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/2211:10 am
ORD
- SRQ
Nonstop3h 00m
United Airlines
Sat 8/224:25 pm
SRQ
- ORD
Nonstop3h 11m
United Airlines
Deal found 5/14![United Airlines logo]()
$494
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 5/303:40 pm
ORD
- SRQ
1 stop6h 35m
United Airlines
Tue 6/24:25 pm
SRQ
- ORD
Nonstop3h 16m
United Airlines
Deal found 5/16![United Airlines logo]()
$495
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/93:22 pm
ORD
- SRQ
1 stop6h 30m
Delta
Mon 7/136:00 am
SRQ
- ORD
1 stop5h 10m
Delta
Deal found 5/17![Delta logo]()
$411
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 9/49:30 am
ORD
- SRQ
1 stop5h 17m
Delta
Mon 9/76:00 am
SRQ
- ORD
1 stop5h 04m
Delta
Deal found 5/15![Delta logo]()
$419
Last-minute flights from Chicago to Siesta KeyDiscover last-minute flight deals from Chicago to Siesta Key. Data last updated May 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Siesta Key. Data last updated May 18, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Sun 5/242:47 pm
MDW
- SRQ
1 stop25h 09m
Allegiant Air
Sun 5/318:32 pm
SRQ
- MDW
1 stop19h 20m
Allegiant Air
Deal found 5/13![Allegiant Air logo]()
$261
This Southwest deal was found by Cheapflights users on 5/13. 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 5/271:30 pm
MDW
- SRQ
Nonstop2h 35m
Southwest
Wed 6/36:05 pm
SRQ
- MDW
1 stop4h 20m
Southwest
Deal found 5/13![Southwest logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 5/282:47 pm
MDW
- SRQ
1 stop25h 14m
Allegiant Air
Thu 6/45:26 pm
SRQ
- MDW
1 stop22h 22m
Allegiant Air
Deal found 5/13![Allegiant Air logo]()
$265
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 6/48:10 am
ORD
- SRQ
1 stop4h 54m
Delta
Tue 6/166:00 am
SRQ
- ORD
1 stop5h 13m
Delta
Deal found 5/15![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/46:23 am
MDW
- SRQ
1 stop6h 41m
Delta
Tue 6/96:00 am
SRQ
- MDW
1 stop5h 09m
Delta
Deal found 5/14![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/45:30 am
ORD
- SRQ
1 stop7h 34m
Delta
Mon 6/86:00 am
SRQ
- ORD
1 stop5h 13m
Delta
Deal found 5/14![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 5/13. 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.
Mon 6/85:05 pm
MDW
- SRQ
1 stop4h 35m
Southwest
Tue 6/96:15 am
SRQ
- MDW
2 stops8h 45m
Southwest
Deal found 5/13![Southwest logo]()
$278
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/95:30 am
ORD
- SRQ
1 stop5h 15m
Delta
Wed 6/176:22 pm
SRQ
- ORD
1 stop6h 37m
Delta
Deal found 5/17![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/165:30 am
ORD
- SRQ
1 stop5h 15m
Delta
Tue 6/236:23 pm
SRQ
- ORD
1 stop6h 36m
Delta
Deal found 5/14![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 5/13. 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.
Tue 6/1612:50 pm
MDW
- SRQ
1 stop5h 02m
Delta
Tue 6/236:00 am
SRQ
- MDW
1 stop5h 09m
Delta
Deal found 5/13![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/161:00 pm
MDW
- SRQ
2 stops8h 00m
Southwest
Tue 6/236:15 am
SRQ
- MDW
1 stop7h 30m
Southwest
Deal found 5/16![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/3011:25 am
MDW
- SRQ
2 stops8h 50m
Southwest
Tue 7/76:15 am
SRQ
- MDW
2 stops7h 10m
Southwest
Deal found 5/17![Southwest logo]()
$267
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 May 18, 2026.
Search for one-way flight options from Chicago to Siesta Key. Find affordable one-way fares based on user searches. Data last updated May 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 8/62:49 pm
MDW
- SRQ
1 stop25h 06m
Allegiant Air
Deal found 5/13![Allegiant Air logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/132:49 pm
MDW
- SRQ
1 stop25h 06m
Allegiant Air
Deal found 5/17![Allegiant Air logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 5/312:47 pm
MDW
- SRQ
1 stop25h 14m
Allegiant Air
Deal found 5/17![Allegiant Air logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Wed 8/51:50 pm
ORD
- SRQ
2 stops41h 38m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 5/282:47 pm
MDW
- SRQ
1 stop25h 14m
Allegiant Air
Deal found 5/13![Allegiant Air logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/812:11 pm
MDW
- SRQ
2 stops43h 17m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$115
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 7/811:10 am
ORD
- SRQ
Nonstop3h 02m
United Airlines
Deal found 5/13![United Airlines logo]()
$119
This Southwest deal was found by Cheapflights users on 5/13. 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.
Tue 6/237:55 am
MDW
- SRQ
Nonstop2h 50m
Southwest
Deal found 5/13![Southwest logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/121:50 pm
ORD
- SRQ
2 stops32h 42m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/126:00 am
MDW
- SRQ
2 stops40h 32m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/162:48 pm
MDW
- SRQ
1 stop25h 01m
Allegiant Air
Deal found 5/18![Allegiant Air logo]()
$122
This Delta deal was found by Cheapflights users on 5/13. 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.
Tue 7/216:35 am
ORD
- SRQ
1 stop6h 38m
Delta
Deal found 5/13![Delta logo]()
$129
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 May 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $253 (Southwest) |
One-way from | $98 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $391 |
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 May 18, 2026.
Use the filters below to find and compare flights from Chicago to Siesta Key that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Wed 10/7
6:05 am-11:55 am
1 stop4h 50m
Sarasota Bradenton Intl
Mon 10/12
6:35 am-8:15 am
Nonstop2h 40m
$263
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Mon 9/21
3:10 pm-9:50 pm
2 stops5h 40m
Sarasota Bradenton Intl
Tue 10/6
2:25 pm-9:50 pm
2 stops8h 25m
$283
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Thu 5/28
6:06 pm-12:18 am
1 stop5h 12m
Sarasota Bradenton Intl
Tue 6/9
6:22 pm-11:59 pm
1 stop6h 37m
$299
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Mon 6/8
5:05 pm-10:40 pm
1 stop4h 35m
Sarasota Bradenton Intl
Tue 6/9
7:05 am-8:45 am
Nonstop2h 40m
$308
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Sat 7/25
6:00 am-11:44 am
1 stop4h 44m
Sarasota Bradenton Intl
Wed 7/29
6:22 pm-10:15 pm
1 stop4h 53m
$309
Quickest round-trip
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Fri 6/26
2:10 pm-5:50 pm
Nonstop2h 40m
Sarasota Bradenton Intl
Tue 6/30
7:05 am-8:45 am
Nonstop2h 40m
$314
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Sun 7/5
6:00 am-11:45 am
1 stop4h 45m
Sarasota Bradenton Intl
Tue 7/14
7:04 am-11:56 am
1 stop5h 52m
$334
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Wed 11/4
10:35 am-3:45 pm
1 stop4h 10m
Sarasota Bradenton Intl
Tue 11/10
4:55 pm-9:45 pm
1 stop5h 50m
$338
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Tue 6/9
6:00 am-11:45 am
1 stop4h 45m
Sarasota Bradenton Intl
Tue 6/16
6:22 pm-10:17 pm
1 stop4h 55m
$339
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Wed 6/17
9:48 am-5:17 pm
1 stop6h 29m
Sarasota Bradenton Intl
Sun 6/21
6:00 am-10:13 am
1 stop5h 13m
$342
Showing 1-10 of 42 resultsSorted by cheapest first
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
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 May 18, 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 18% 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 May 16, 2026.
Travelers seeking maximum savings on their Chicago to Siesta Key flight should consider departing on Wednesday afternoons 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 May 18, 2026.
The most flights from CHI to S1E are scheduled on a Friday (45 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 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 May 18, 2026.
Read through reviews of airlines operating flights from Chicago to Siesta Key, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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
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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 May 18, 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 May 18, 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 May 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$48 | Average$193 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$66 | Average$189 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$99 | Average$217 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$109 | Average$333 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$144 | Average$259 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$340 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$344 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$158 | Average$365 | FlexibilityNo cancel fee | On-time63% |