Flights from Chicago to Siesta Key

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Sep 13 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$197 Roundtrip, found 2 days ago

$197

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Sep 13 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $197 found 2 days ago

Sat, Aug 9 - Wed, Aug 13

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$259 Roundtrip, found 3 days ago

$259

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Aug 9 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 13, priced at $259 found 3 days ago

Tue, Aug 26 - Wed, Sep 3

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$280 Roundtrip, found 1 day ago

$280

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 3, priced at $280 found 1 day ago

Sat, Sep 13 - Thu, Sep 18

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$288 Roundtrip, found 2 days ago

$288

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Sep 13 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Thu, Sep 18, priced at $288 found 2 days ago

Fri, Sep 12 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$295 Roundtrip, found 2 days ago

$295

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Sep 12 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $295 found 2 days ago

Thu, Aug 28 - Wed, Sep 3

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$321 Roundtrip, found 1 day ago

$321

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Aug 28 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 3, priced at $321 found 1 day ago

Tue, Aug 26 - Fri, Sep 5

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$326 Roundtrip, found 1 day ago

$326

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Fri, Sep 5, priced at $326 found 1 day ago

Tue, Aug 26 - Tue, Sep 2

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$338 Roundtrip, found 1 day ago

$338

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Tue, Sep 2, priced at $338 found 1 day ago

Fri, Aug 29 - Sat, Aug 30

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$345 Roundtrip, found 1 day ago

$345

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Aug 29 from Midway Intl. to Sarasota-Bradenton Intl., returning Sat, Aug 30, priced at $345 found 1 day ago

Mon, Sep 1 - Thu, Sep 4

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$347 Roundtrip, found 1 day ago

$347

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Sep 1 from Midway Intl. to Sarasota-Bradenton Intl., returning Thu, Sep 4, priced at $347 found 1 day ago

Fri, Aug 29 - Thu, Sep 4

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$354 Roundtrip, found 1 day ago

$354

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Aug 29 from Midway Intl. to Sarasota-Bradenton Intl., returning Thu, Sep 4, priced at $354 found 1 day ago

Wed, Aug 13 - Wed, Aug 20

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$385 Roundtrip, found 3 hours ago

$385

Roundtrip

found 3 hours ago

Select Delta flight, departing Wed, Aug 13 from Midway Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 20, priced at $385 found 3 hours ago

Fri, Aug 29 - Mon, Sep 1

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$386 Roundtrip, found 1 day ago

$386

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Aug 29 from Midway Intl. to Sarasota-Bradenton Intl., returning Mon, Sep 1, priced at $386 found 1 day ago

Sat, Aug 9 - Fri, Aug 15

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$389 Roundtrip, found 3 days ago

$389

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Aug 9 from Midway Intl. to Sarasota-Bradenton Intl., returning Fri, Aug 15, priced at $389 found 3 days ago

Fri, Aug 29 - Sun, Aug 31

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$393 Roundtrip, found 1 day ago

$393

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Aug 29 from Midway Intl. to Sarasota-Bradenton Intl., returning Sun, Aug 31, priced at $393 found 1 day ago

Wed, Aug 13 - Thu, Aug 21

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$394 Roundtrip, found 3 hours ago

$394

Roundtrip

found 3 hours ago

Select Delta flight, departing Wed, Aug 13 from Midway Intl. to Sarasota-Bradenton Intl., returning Thu, Aug 21, priced at $394 found 3 hours ago

Wed, Aug 13 - Fri, Aug 22

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$414 Roundtrip, found 3 hours ago

$414

Roundtrip

found 3 hours ago

Select Delta flight, departing Wed, Aug 13 from Midway Intl. to Sarasota-Bradenton Intl., returning Fri, Aug 22, priced at $414 found 3 hours ago

Mon, Aug 4 - Sat, Aug 16

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$431 Roundtrip, found 3 days ago

$431

Roundtrip

found 3 days ago

Select Delta flight, departing Mon, Aug 4 from Midway Intl. to Sarasota-Bradenton Intl., returning Sat, Aug 16, priced at $431 found 3 days ago

Wed, Aug 13 - Tue, Aug 19

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$451 Roundtrip, found 3 hours ago

$451

Roundtrip

found 3 hours ago

Select Delta flight, departing Wed, Aug 13 from Midway Intl. to Sarasota-Bradenton Intl., returning Tue, Aug 19, priced at $451 found 3 hours ago

Fri, Nov 28 - Sun, Nov 30

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$1,260 Roundtrip, found 3 days ago

$1,260

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Fri, Nov 28 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sun, Nov 30, priced at $1,260 found 3 days ago