Flights from Chicago to Sarasota

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.

Mon, Aug 25 - Fri, Aug 29

ORD

O'Hare Intl.

TPA

Tampa Intl.

$108 Roundtrip, found 1 hour ago

$108

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Mon, Aug 25 from O'Hare Intl. to Tampa Intl., returning Fri, Aug 29, priced at $108 found 1 hour ago

Thu, Aug 28 - Sat, Aug 30

ORD

O'Hare Intl.

TPA

Tampa Intl.

$114 Roundtrip, found 1 hour ago

$114

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Thu, Aug 28 from O'Hare Intl. to Tampa Intl., returning Sat, Aug 30, priced at $114 found 1 hour ago

Fri, Aug 29 - Sun, Aug 31

ORD

O'Hare Intl.

TPA

Tampa Intl.

$120 Roundtrip, found 1 hour ago

$120

Roundtrip

found 1 hour ago

Select Spirit Airlines flight, departing Fri, Aug 29 from O'Hare Intl. to Tampa Intl., returning Sun, Aug 31, priced at $120 found 1 hour ago

Sun, Aug 31 - Mon, Sep 8

MDW

Midway Intl.

TPA

Tampa Intl.

$123 Roundtrip, found 1 hour ago

$123

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Sun, Aug 31 from Midway Intl. to Tampa Intl., returning Mon, Sep 8, priced at $123 found 1 hour ago

Sun, Aug 31 - Sun, Aug 31

MDW

Midway Intl.

TPA

Tampa Intl.

$124 Roundtrip, found 1 hour ago

$124

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Sun, Aug 31 from Midway Intl. to Tampa Intl., returning Sun, Aug 31, priced at $124 found 1 hour ago

Mon, Aug 25 - Tue, Aug 26

ORD

O'Hare Intl.

TPA

Tampa Intl.

$130 Roundtrip, found 1 hour ago

$130

Roundtrip

found 1 hour ago

Select Spirit Airlines flight, departing Mon, Aug 25 from O'Hare Intl. to Tampa Intl., returning Tue, Aug 26, priced at $130 found 1 hour ago

Fri, Aug 29 - Mon, Sep 8

MDW

Midway Intl.

TPA

Tampa Intl.

$131 Roundtrip, found 1 hour ago

$131

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Fri, Aug 29 from Midway Intl. to Tampa Intl., returning Mon, Sep 8, priced at $131 found 1 hour ago

Fri, Aug 29 - Sun, Aug 31

MDW

Midway Intl.

TPA

Tampa Intl.

$132 Roundtrip, found 1 hour ago

$132

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Fri, Aug 29 from Midway Intl. to Tampa Intl., returning Sun, Aug 31, priced at $132 found 1 hour ago

Thu, Aug 28 - Sat, Aug 30

ORD

O'Hare Intl.

TPA

Tampa Intl.

$139 Roundtrip, found 1 hour ago

$139

Roundtrip

found 1 hour ago

Select United flight, departing Thu, Aug 28 from O'Hare Intl. to Tampa Intl., returning Sat, Aug 30, priced at $139 found 1 hour ago

Sun, Aug 24 - Sun, Sep 7

ORD

O'Hare Intl.

TPA

Tampa Intl.

$140 Roundtrip, found 4 days ago

$140

Roundtrip

found 4 days ago

Select United flight, departing Sun, Aug 24 from O'Hare Intl. to Tampa Intl., returning Sun, Sep 7, priced at $140 found 4 days ago

Fri, Aug 29 - Fri, Aug 29

MDW

Midway Intl.

TPA

Tampa Intl.

$140 Roundtrip, found 1 hour ago

$140

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Fri, Aug 29 from Midway Intl. to Tampa Intl., returning Fri, Aug 29, priced at $140 found 1 hour ago

Mon, Sep 1 - Mon, Sep 8

MDW

Midway Intl.

TPA

Tampa Intl.

$145 Roundtrip, found 1 hour ago

$145

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Mon, Sep 1 from Midway Intl. to Tampa Intl., returning Mon, Sep 8, priced at $145 found 1 hour ago

Sun, Aug 31 - Mon, Sep 1

MDW

Midway Intl.

TPA

Tampa Intl.

$146 Roundtrip, found 1 hour ago

$146

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Sun, Aug 31 from Midway Intl. to Tampa Intl., returning Mon, Sep 1, priced at $146 found 1 hour ago

Sat, Oct 11 - Sat, Oct 18

ORD

O'Hare Intl.

TPA

Tampa Intl.

$150 Roundtrip, found 21 hours ago

$150

Roundtrip

found 21 hours ago

Select United flight, departing Sat, Oct 11 from O'Hare Intl. to Tampa Intl., returning Sat, Oct 18, priced at $150 found 21 hours ago

Sat, Aug 16 - Thu, Sep 4

ORD

O'Hare Intl.

TPA

Tampa Intl.

$150 Roundtrip, found 6 days ago

$150

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Aug 16 from O'Hare Intl. to Tampa Intl., returning Thu, Sep 4, priced at $150 found 6 days ago

Thu, Aug 28 - Sat, Aug 30

ORD

O'Hare Intl.

TPA

Tampa Intl.

$157 Roundtrip, found 1 hour ago

$157

Roundtrip

found 1 hour ago

Select United flight, departing Thu, Aug 28 from O'Hare Intl. to Tampa Intl., returning Sat, Aug 30, priced at $157 found 1 hour ago

Thu, Aug 28 - Sat, Aug 30

ORD

O'Hare Intl.

TPA

Tampa Intl.

$157 Roundtrip, found 1 hour ago

$157

Roundtrip

found 1 hour ago

Select American Airlines flight, departing Thu, Aug 28 from O'Hare Intl. to Tampa Intl., returning Sat, Aug 30, priced at $157 found 1 hour ago

Sat, Aug 30 - Sat, Aug 30

MDW

Midway Intl.

TPA

Tampa Intl.

$191 Roundtrip, found 1 hour ago

$191

Roundtrip

found 1 hour ago

Select Delta flight, departing Sat, Aug 30 from Midway Intl. to Tampa Intl., returning Sat, Aug 30, priced at $191 found 1 hour ago

Wed, Nov 19 - Sun, Nov 23

ORD

O'Hare Intl.

TPA

Tampa Intl.

$240 Roundtrip, found 1 day ago

$240

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Wed, Nov 19 from O'Hare Intl. to Tampa Intl., returning Sun, Nov 23, priced at $240 found 1 day ago

Sat, Nov 1 - Sat, Nov 8

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$291 Roundtrip, found 2 days ago

$291

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Nov 1 from Midway Intl. to Sarasota-Bradenton Intl., returning Sat, Nov 8, priced at $291 found 2 days ago