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.

Tue, Aug 26 - Wed, Sep 3

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$280 Roundtrip, found 6 days ago

$280

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 3, priced at $280 found 6 days ago

Thu, Aug 28 - Wed, Sep 3

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$321 Roundtrip, found 6 days ago

$321

Roundtrip

found 6 days ago

Select Delta flight, departing Thu, Aug 28 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 3, priced at $321 found 6 days ago

Tue, Aug 26 - Fri, Sep 5

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$326 Roundtrip, found 6 days ago

$326

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Fri, Sep 5, priced at $326 found 6 days ago

Tue, Aug 26 - Tue, Sep 2

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$338 Roundtrip, found 6 days ago

$338

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Tue, Sep 2, priced at $338 found 6 days ago

Fri, Aug 29 - Sat, Aug 30

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$345 Roundtrip, found 6 days ago

$345

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Aug 29 from Midway Intl. to Sarasota-Bradenton Intl., returning Sat, Aug 30, priced at $345 found 6 days ago

Mon, Sep 1 - Thu, Sep 4

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$347 Roundtrip, found 6 days ago

$347

Roundtrip

found 6 days ago

Select Delta flight, departing Mon, Sep 1 from Midway Intl. to Sarasota-Bradenton Intl., returning Thu, Sep 4, priced at $347 found 6 days ago

Fri, Aug 29 - Thu, Sep 4

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$354 Roundtrip, found 6 days ago

$354

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Aug 29 from Midway Intl. to Sarasota-Bradenton Intl., returning Thu, Sep 4, priced at $354 found 6 days ago

Wed, Aug 13 - Wed, Aug 20

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$385 Roundtrip, found 4 days ago

$385

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Aug 13 from Midway Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 20, priced at $385 found 4 days ago

Fri, Aug 29 - Mon, Sep 1

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$386 Roundtrip, found 6 days ago

$386

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Aug 29 from Midway Intl. to Sarasota-Bradenton Intl., returning Mon, Sep 1, priced at $386 found 6 days ago

Fri, Aug 29 - Sun, Aug 31

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$393 Roundtrip, found 6 days ago

$393

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Aug 29 from Midway Intl. to Sarasota-Bradenton Intl., returning Sun, Aug 31, priced at $393 found 6 days ago

Wed, Aug 13 - Thu, Aug 21

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$394 Roundtrip, found 4 days ago

$394

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Aug 13 from Midway Intl. to Sarasota-Bradenton Intl., returning Thu, Aug 21, priced at $394 found 4 days ago

Wed, Aug 13 - Fri, Aug 22

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$414 Roundtrip, found 4 days ago

$414

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Aug 13 from Midway Intl. to Sarasota-Bradenton Intl., returning Fri, Aug 22, priced at $414 found 4 days ago

Wed, Aug 13 - Tue, Aug 19

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$451 Roundtrip, found 4 days ago

$451

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Aug 13 from Midway Intl. to Sarasota-Bradenton Intl., returning Tue, Aug 19, priced at $451 found 4 days ago

Wed, Aug 13 - Sun, Aug 24

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$458 Roundtrip, found 4 days ago

$458

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Aug 13 from Midway Intl. to Sarasota-Bradenton Intl., returning Sun, Aug 24, priced at $458 found 4 days ago

Wed, Aug 13 - Mon, Aug 18

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$473 Roundtrip, found 4 days ago

$473

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Aug 13 from Midway Intl. to Sarasota-Bradenton Intl., returning Mon, Aug 18, priced at $473 found 4 days ago

Mon, Aug 11 - Wed, Aug 20

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$475 Roundtrip, found 4 days ago

$475

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Aug 11 from Midway Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 20, priced at $475 found 4 days ago

Mon, Aug 11 - Thu, Aug 21

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$484 Roundtrip, found 4 days ago

$484

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Aug 11 from Midway Intl. to Sarasota-Bradenton Intl., returning Thu, Aug 21, priced at $484 found 4 days ago

Mon, Aug 11 - Fri, Aug 22

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$504 Roundtrip, found 4 days ago

$504

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Aug 11 from Midway Intl. to Sarasota-Bradenton Intl., returning Fri, Aug 22, priced at $504 found 4 days ago

Fri, Aug 29 - Sun, Aug 31

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$533 Roundtrip, found 6 days ago

$533

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Aug 29 from Midway Intl. to Sarasota-Bradenton Intl., returning Sun, Aug 31, priced at $533 found 6 days ago

Mon, Aug 11 - Sun, Aug 24

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$548 Roundtrip, found 4 days ago

$548

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Aug 11 from Midway Intl. to Sarasota-Bradenton Intl., returning Sun, Aug 24, priced at $548 found 4 days ago