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 1 day ago

$197

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Sep 13 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $197 found 1 day ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$233 Roundtrip, found 6 days ago

$233

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $233 found 6 days ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$236 Roundtrip, found 6 days ago

$236

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $236 found 6 days ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$246 Roundtrip, found 6 days ago

$246

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $246 found 6 days ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$250 Roundtrip, found 6 days ago

$250

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $250 found 6 days ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$253 Roundtrip, found 6 days ago

$253

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $253 found 6 days ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$256 Roundtrip, found 6 days ago

$256

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $256 found 6 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

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$261 Roundtrip, found 6 days ago

$261

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $261 found 6 days ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$269 Roundtrip, found 6 days ago

$269

Roundtrip

found 6 days ago

Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $269 found 6 days ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$273 Roundtrip, found 6 days ago

$273

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $273 found 6 days ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$277 Roundtrip, found 6 days ago

$277

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $277 found 6 days ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$279 Roundtrip, found 6 days ago

$279

Roundtrip

found 6 days ago

Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $279 found 6 days ago

Tue, Aug 26 - Wed, Sep 3

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$280 Roundtrip, found 9 hours ago

$280

Roundtrip

found 9 hours ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 3, priced at $280 found 9 hours ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$284 Roundtrip, found 6 days ago

$284

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $284 found 6 days ago

Sat, Sep 13 - Thu, Sep 18

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$288 Roundtrip, found 1 day ago

$288

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Sep 13 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Thu, Sep 18, priced at $288 found 1 day ago

Fri, Sep 12 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$295 Roundtrip, found 1 day ago

$295

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Sep 12 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $295 found 1 day ago

Wed, Sep 17 - Sat, Sep 20

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$296 Roundtrip, found 6 days ago

$296

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Sep 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 20, priced at $296 found 6 days ago

Thu, Sep 18 - Sun, Sep 21

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$298 Roundtrip, found 6 days ago

$298

Roundtrip

found 6 days ago

Select American Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sun, Sep 21, priced at $298 found 6 days ago

Fri, Nov 28 - Sun, Nov 30

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$1,260 Roundtrip, found 2 days ago

$1,260

Roundtrip

found 2 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 2 days ago