$137+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TPA
Apr 29 — May 61
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 April or July, booked 17 days in advance, depart on a Thursday or Sunday 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 March 30, 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 March 30, 2026.
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/222:40 pm
ORD
- SRQ
1 stop4h 50m
Southwest
Sat 4/256:25 am
SRQ
- ORD
1 stop7h 45m
Southwest
Deal found 3/30![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 3/27. 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.
Tue 4/211:00 pm
MDW
- SRQ
1 stop7h 15m
Southwest
Tue 4/286:05 pm
SRQ
- MDW
1 stop4h 20m
Southwest
Deal found 3/27![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 3/25. 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.
Sat 4/253:15 pm
ORD
- SRQ
1 stop5h 25m
Southwest
Sat 5/211:40 am
SRQ
- ORD
1 stop4h 50m
Southwest
Deal found 3/25![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 3/26. 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 4/237:50 am
MDW
- SRQ
1 stop9h 05m
Southwest
Tue 4/287:20 am
SRQ
- MDW
2 stops7h 45m
Southwest
Deal found 3/26![Southwest logo]()
$269
This American Airlines deal was found by Cheapflights users on 3/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:59 pm
ORD
- SRQ
Nonstop2h 48m
American Airlines
Sat 5/168:46 am
SRQ
- ORD
Nonstop3h 09m
American Airlines
Deal found 3/25![American Airlines logo]()
$271
This Southwest deal was found by Cheapflights users on 3/26. 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 5/296:55 pm
MDW
- SRQ
Nonstop2h 35m
Southwest
Wed 6/34:10 pm
SRQ
- MDW
1 stop4h 50m
Southwest
Deal found 3/26![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 3/27. 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.
Tue 4/211:00 pm
MDW
- SRQ
2 stops7h 40m
Southwest
Mon 4/276:10 pm
SRQ
- MDW
1 stop6h 55m
Southwest
Deal found 3/27![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 3/26. 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.
Sat 5/2312:05 pm
MDW
- SRQ
2 stops8h 35m
Southwest
Sat 5/305:45 pm
SRQ
- MDW
1 stop5h 50m
Southwest
Deal found 3/26![Southwest logo]()
$274
This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:54 pm
ORD
- SRQ
1 stop5h 58m
American Airlines
Mon 4/2712:47 pm
SRQ
- ORD
Nonstop3h 10m
American Airlines
Deal found 3/27![American Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:05 pm
ORD
- SRQ
1 stop5h 23m
Delta
Tue 5/2611:28 am
SRQ
- ORD
1 stop6h 27m
Delta
Deal found 3/25![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 3/26. 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 5/296:55 pm
MDW
- SRQ
Nonstop2h 35m
Southwest
Tue 6/29:20 am
SRQ
- MDW
2 stops7h 25m
Southwest
Deal found 3/26![Southwest logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:16 pm
ORD
- SRQ
1 stop27h 21m
Multiple Airlines
Mon 4/206:35 pm
SRQ
- ORD
2 stops40h 01m
Multiple Airlines
Deal found 3/26![Multiple Airlines logo]()
$277
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 March 30, 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 March 30, 2026.
This Southwest deal was found by Cheapflights users on 3/29. 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.
Sat 5/169:20 am
MDW
- SRQ
2 stops9h 05m
Southwest
Tue 5/199:20 am
SRQ
- MDW
2 stops7h 25m
Southwest
Deal found 3/29![Southwest logo]()
$278
This Delta deal was found by Cheapflights users on 3/27. 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 4/2110:41 am
MDW
- SRQ
1 stop5h 37m
Delta
Tue 4/286:00 am
SRQ
- MDW
1 stop4h 56m
Delta
Deal found 3/27![Delta logo]()
$311
This United Airlines deal was found by Cheapflights users on 3/29. 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 5/84:35 pm
ORD
- SRQ
Nonstop3h 07m
United Airlines
Sun 5/109:05 am
SRQ
- ORD
Nonstop3h 14m
United Airlines
Deal found 3/29![United Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 3/25. 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.
Sat 5/212:45 pm
MDW
- SRQ
1 stop6h 35m
Southwest
Tue 5/55:50 pm
SRQ
- MDW
Nonstop2h 45m
Southwest
Deal found 3/25![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 3/27. 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 4/185:21 pm
MDW
- SRQ
1 stop6h 13m
Delta
Sat 4/256:25 pm
SRQ
- MDW
1 stop5h 03m
Delta
Deal found 3/27![Delta logo]()
$323
This Southwest deal was found by Cheapflights users on 3/26. 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 5/272:40 pm
ORD
- SRQ
1 stop4h 50m
Southwest
Sun 5/317:00 am
SRQ
- ORD
2 stops12h 25m
Southwest
Deal found 3/26![Southwest logo]()
$302
This Delta deal was found by Cheapflights users on 3/27. 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.
Thu 4/167:00 am
ORD
- SRQ
1 stop4h 56m
Delta
Mon 4/206:00 am
SRQ
- ORD
1 stop5h 09m
Delta
Deal found 3/27![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/811:05 am
ORD
- SRQ
Nonstop3h 02m
United Airlines
Wed 6/174:15 pm
SRQ
- ORD
Nonstop3h 16m
United Airlines
Deal found 3/29![United Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 3/25. 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 4/249:00 am
MDW
- SRQ
1 stop8h 10m
Southwest
Fri 5/17:05 am
SRQ
- MDW
Nonstop2h 50m
Southwest
Deal found 3/25![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:59 am
MDW
- SRQ
1 stop4h 47m
Delta
Sat 5/306:00 am
SRQ
- MDW
1 stop4h 59m
Delta
Deal found 3/29![Delta logo]()
$340
This United Airlines deal was found by Cheapflights users on 3/25. 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 5/74:35 pm
ORD
- SRQ
Nonstop3h 06m
United Airlines
Sun 5/105:00 pm
SRQ
- ORD
1 stop9h 27m
United Airlines
Deal found 3/25![United Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 3/26. 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 4/237:50 am
MDW
- SRQ
1 stop9h 05m
Southwest
Sun 4/267:20 am
SRQ
- MDW
Nonstop2h 50m
Southwest
Deal found 3/26![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 3/27. 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 4/145:21 pm
MDW
- SRQ
1 stop4h 26m
Delta
Tue 4/216:26 pm
SRQ
- MDW
1 stop5h 02m
Delta
Deal found 3/27![Delta logo]()
$374
This Southwest deal was found by Cheapflights users on 3/27. 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 4/132:40 pm
ORD
- SRQ
2 stops6h 00m
Southwest
Sat 4/186:25 am
SRQ
- ORD
2 stops10h 05m
Southwest
Deal found 3/27![Southwest logo]()
$362
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:00 am
ORD
- SRQ
1 stop4h 56m
Delta
Mon 4/207:59 pm
SRQ
- ORD
1 stop5h 00m
Delta
Deal found 3/29![Delta logo]()
$392
This Southwest deal was found by Cheapflights users on 3/28. 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.
Thu 4/309:00 am
MDW
- SRQ
1 stop8h 10m
Southwest
Fri 5/14:30 pm
SRQ
- MDW
2 stops7h 15m
Southwest
Deal found 3/28![Southwest logo]()
$369
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:15 am
ORD
- SRQ
1 stop5h 29m
Delta
Sun 8/93:18 pm
SRQ
- ORD
1 stop7h 50m
Delta
Deal found 3/29![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 3/28. 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.
Thu 4/302:40 pm
ORD
- SRQ
1 stop5h 35m
Southwest
Sun 5/36:30 am
SRQ
- ORD
2 stops10h 00m
Southwest
Deal found 3/28![Southwest logo]()
$380
This Southwest deal was found by Cheapflights users on 3/29. 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.
Fri 5/86:00 am
ORD
- SRQ
2 stops11h 10m
Southwest
Sun 5/107:00 am
SRQ
- ORD
2 stops12h 25m
Southwest
Deal found 3/29![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
ORD
- SRQ
2 stops14h 35m
Southwest
Sun 5/317:00 am
SRQ
- ORD
2 stops15h 55m
Southwest
Deal found 3/29![Southwest logo]()
$393
Last-minute flights from Chicago to Siesta KeyDiscover last-minute flight deals from Chicago to Siesta Key. Data last updated March 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Siesta Key. Data last updated March 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:16 pm
ORD
- SRQ
1 stop27h 21m
Multiple Airlines
Mon 4/206:35 pm
SRQ
- ORD
2 stops40h 01m
Multiple Airlines
Deal found 3/26![Multiple Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 3/26. 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.
Sat 4/183:15 pm
ORD
- SRQ
1 stop5h 25m
Southwest
Sat 4/2511:40 am
SRQ
- ORD
1 stop4h 50m
Southwest
Deal found 3/26![Southwest logo]()
$280
This Southwest deal was found by Cheapflights users on 3/26. 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.
Sat 4/182:15 pm
MDW
- SRQ
1 stop4h 10m
Southwest
Sat 4/255:45 pm
SRQ
- MDW
1 stop5h 50m
Southwest
Deal found 3/26![Southwest logo]()
$280
This Southwest deal was found by Cheapflights users on 3/27. 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.
Tue 4/211:00 pm
MDW
- SRQ
1 stop7h 15m
Southwest
Tue 4/286:05 pm
SRQ
- MDW
1 stop4h 20m
Southwest
Deal found 3/27![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/222:40 pm
ORD
- SRQ
1 stop4h 50m
Southwest
Sat 4/256:25 am
SRQ
- ORD
1 stop7h 45m
Southwest
Deal found 3/30![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 3/26. 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 4/237:50 am
MDW
- SRQ
1 stop9h 05m
Southwest
Tue 4/287:20 am
SRQ
- MDW
2 stops7h 45m
Southwest
Deal found 3/26![Southwest logo]()
$269
This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:54 pm
ORD
- SRQ
1 stop5h 58m
American Airlines
Mon 4/2712:47 pm
SRQ
- ORD
Nonstop3h 10m
American Airlines
Deal found 3/27![American Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 3/25. 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.
Sat 4/253:15 pm
ORD
- SRQ
1 stop5h 25m
Southwest
Sat 5/211:40 am
SRQ
- ORD
1 stop4h 50m
Southwest
Deal found 3/25![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 3/26. 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.
Sat 4/252:15 pm
MDW
- SRQ
2 stops6h 25m
Southwest
Sat 5/26:25 am
SRQ
- MDW
2 stops6h 50m
Southwest
Deal found 3/26![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 3/29. 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 4/2811:55 am
ORD
- SRQ
2 stops8h 45m
Southwest
Tue 5/59:20 am
SRQ
- ORD
2 stops10h 05m
Southwest
Deal found 3/29![Southwest logo]()
$278
This Priceline deal was found by Cheapflights users on 3/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/299:41 am
ORD
- SRQ
1 stop11h 23m
Multiple Airlines
Mon 5/412:01 pm
SRQ
- ORD
1 stop9h 02m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$276
This American Airlines deal was found by Cheapflights users on 3/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:59 pm
ORD
- SRQ
Nonstop2h 48m
American Airlines
Sat 5/168:46 am
SRQ
- ORD
Nonstop3h 09m
American Airlines
Deal found 3/25![American Airlines logo]()
$271
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 March 30, 2026.
Search for one-way flight options from Chicago to Siesta Key. Find affordable one-way fares based on user searches. Data last updated March 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:15 pm
MDW
- SRQ
2 stops27h 42m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$137
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:55 pm
MDW
- SRQ
2 stops6h 45m
Southwest
Deal found 3/30![Southwest logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:15 pm
ORD
- SRQ
3 stops43h 17m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
MDW
- SRQ
2 stops32h 31m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:15 pm
MDW
- SRQ
2 stops52h 26m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/178:52 pm
ORD
- SRQ
2 stops21h 49m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:28 am
ORD
- SRQ
2 stops27h 34m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$145
This United Airlines deal was found by Cheapflights users on 3/26. 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 5/44:30 pm
ORD
- SRQ
1 stop6h 29m
United Airlines
Deal found 3/26![United Airlines logo]()
$146
This Southwest deal was found by Cheapflights users on 3/26. 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 4/1512:50 pm
MDW
- SRQ
2 stops7h 25m
Southwest
Deal found 3/26![Southwest logo]()
$146
This United Airlines deal was found by Cheapflights users on 3/25. 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 4/2111:00 am
ORD
- SRQ
Nonstop3h 01m
United Airlines
Deal found 3/25![United Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
MDW
- SRQ
2 stops37h 27m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:05 am
ORD
- SRQ
2 stops34h 37m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$150
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 March 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $267 (Southwest) |
One-way from | $137 (Kiwi.com) |
Popular in | December |
Cheapest in | April |
Average price | $443 |
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 March 30, 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
Sat 5/16
9:20 am-7:25 pm
2 stops9h 05m
Sarasota Bradenton Intl
Tue 5/19
9:20 am-3:45 pm
2 stops7h 25m
$278
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Sat 5/2
12:45 pm-8:20 pm
1 stop6h 35m
Sarasota Bradenton Intl
Tue 5/5
5:50 pm-7:35 pm
Nonstop2h 45m
$295
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Wed 5/27
2:40 pm-8:30 pm
1 stop4h 50m
Sarasota Bradenton Intl
Sun 5/31
7:00 am-6:25 pm
2 stops12h 25m
$302
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Tue 4/21
10:41 am-5:18 pm
1 stop5h 37m
Sarasota Bradenton Intl
Tue 4/28
6:00 am-9:56 am
1 stop4h 56m
$311
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Sat 4/18
5:21 pm-12:34 am
1 stop6h 13m
Sarasota Bradenton Intl
Sat 4/25
6:25 pm-10:28 pm
1 stop5h 03m
$323
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Fri 4/24
9:00 am-6:10 pm
1 stop8h 10m
Sarasota Bradenton Intl
Fri 5/1
7:05 am-8:55 am
Nonstop2h 50m
$329
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Thu 4/16
7:00 am-12:56 pm
1 stop4h 56m
Sarasota Bradenton Intl
Mon 4/20
6:00 am-10:09 am
1 stop5h 09m
$335
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Thu 5/28
10:59 am-4:46 pm
1 stop4h 47m
Sarasota Bradenton Intl
Sat 5/30
6:00 am-9:59 am
1 stop4h 59m
$340
ChicagoSarasota
ORD - SRQ
ORDSRQ
Chicago O'Hare Intl
Fri 5/8
4:35 pm-8:42 pm
Nonstop3h 07m
Sarasota Bradenton Intl
Sun 5/10
9:05 am-11:19 am
Nonstop3h 14m
$351
ChicagoSarasota
MDW - SRQ
MDWSRQ
Chicago Midway
Thu 4/23
7:50 am-5:55 pm
1 stop9h 05m
Sarasota Bradenton Intl
Sun 4/26
7:20 am-9:10 am
Nonstop2h 50m
$358
Showing 1-10 of 40 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.
MDW-SRQ
ORD-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
MDW-SRQ
ORD-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 March 13, 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 March 30, 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 14% 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 March 28, 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 March 30, 2026.
The most flights from CHI to S1E are scheduled on a Monday (52 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (32 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 March 30, 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.
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
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
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 March 30, 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 March 30, 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 March 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$48 | Average$193 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$66 | Average$182 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$87 | Average$217 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$119 | Average$272 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$130 | Average$333 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$338 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$340 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$361 | FlexibilityNo cancel fee | On-time63% |