Flights from Sarasota to Chicago

Cheapest flights from Sarasota

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, Oct 6 - Mon, Oct 13

TPA

Tampa Intl.

MDW

Midway Intl.

$168 Roundtrip, found 4 days ago

$168

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Mon, Oct 6 from Tampa Intl. to Midway Intl., returning Mon, Oct 13, priced at $168 found 4 days ago

Fri, Oct 3 - Mon, Oct 13

TPA

Tampa Intl.

MDW

Midway Intl.

$180 Roundtrip, found 4 days ago

$180

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Oct 3 from Tampa Intl. to Midway Intl., returning Mon, Oct 13, priced at $180 found 4 days ago

Fri, Oct 3 - Sun, Oct 12

TPA

Tampa Intl.

MDW

Midway Intl.

$192 Roundtrip, found 4 days ago

$192

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Oct 3 from Tampa Intl. to Midway Intl., returning Sun, Oct 12, priced at $192 found 4 days ago

Fri, Oct 3 - Sat, Oct 11

TPA

Tampa Intl.

MDW

Midway Intl.

$195 Roundtrip, found 4 days ago

$195

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Oct 3 from Tampa Intl. to Midway Intl., returning Sat, Oct 11, priced at $195 found 4 days ago

Fri, Oct 3 - Sat, Oct 11

TPA

Tampa Intl.

MDW

Midway Intl.

$197 Roundtrip, found 4 days ago

$197

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Oct 3 from Tampa Intl. to Midway Intl., returning Sat, Oct 11, priced at $197 found 4 days ago

Thu, Oct 2 - Fri, Oct 10

TPA

Tampa Intl.

MDW

Midway Intl.

$204 Roundtrip, found 4 days ago

$204

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Oct 2 from Tampa Intl. to Midway Intl., returning Fri, Oct 10, priced at $204 found 4 days ago

Fri, Aug 15 - Sat, Aug 16

SRQ

Sarasota-Bradenton Intl.

ORD

O'Hare Intl.

$209 Roundtrip, found 13 hours ago

$209

Roundtrip

found 13 hours ago

Select Delta flight, departing Fri, Aug 15 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $209 found 13 hours ago

Fri, Oct 3 - Fri, Oct 10

TPA

Tampa Intl.

MDW

Midway Intl.

$210 Roundtrip, found 4 days ago

$210

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Oct 3 from Tampa Intl. to Midway Intl., returning Fri, Oct 10, priced at $210 found 4 days ago

Tue, Sep 30 - Mon, Oct 13

TPA

Tampa Intl.

MDW

Midway Intl.

$220 Roundtrip, found 4 days ago

$220

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Tue, Sep 30 from Tampa Intl. to Midway Intl., returning Mon, Oct 13, priced at $220 found 4 days ago

Wed, Oct 1 - Sat, Oct 11

TPA

Tampa Intl.

MDW

Midway Intl.

$221 Roundtrip, found 4 days ago

$221

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Oct 1 from Tampa Intl. to Midway Intl., returning Sat, Oct 11, priced at $221 found 4 days ago

Fri, Oct 3 - Sat, Oct 11

TPA

Tampa Intl.

MDW

Midway Intl.

$223 Roundtrip, found 4 days ago

$223

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Oct 3 from Tampa Intl. to Midway Intl., returning Sat, Oct 11, priced at $223 found 4 days ago

Wed, Oct 1 - Wed, Oct 8

TPA

Tampa Intl.

MDW

Midway Intl.

$230 Roundtrip, found 4 days ago

$230

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Oct 1 from Tampa Intl. to Midway Intl., returning Wed, Oct 8, priced at $230 found 4 days ago

Tue, Sep 30 - Sun, Oct 12

TPA

Tampa Intl.

MDW

Midway Intl.

$232 Roundtrip, found 4 days ago

$232

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Tue, Sep 30 from Tampa Intl. to Midway Intl., returning Sun, Oct 12, priced at $232 found 4 days ago

Tue, Aug 12 - Sat, Aug 16

SRQ

Sarasota-Bradenton Intl.

ORD

O'Hare Intl.

$234 Roundtrip, found 13 hours ago

$234

Roundtrip

found 13 hours ago

Select Delta flight, departing Tue, Aug 12 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $234 found 13 hours ago

Thu, Oct 2 - Fri, Oct 10

TPA

Tampa Intl.

MDW

Midway Intl.

$239 Roundtrip, found 4 days ago

$239

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Oct 2 from Tampa Intl. to Midway Intl., returning Fri, Oct 10, priced at $239 found 4 days ago

Fri, Aug 15 - Mon, Aug 18

SRQ

Sarasota-Bradenton Intl.

ORD

O'Hare Intl.

$239 Roundtrip, found 13 hours ago

$239

Roundtrip

found 13 hours ago

Select Delta flight, departing Fri, Aug 15 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $239 found 13 hours ago

Mon, Oct 6 - Wed, Oct 8

TPA

Tampa Intl.

MDW

Midway Intl.

$240 Roundtrip, found 4 days ago

$240

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Oct 6 from Tampa Intl. to Midway Intl., returning Wed, Oct 8, priced at $240 found 4 days ago

Fri, Oct 3 - Sat, Oct 11

TPA

Tampa Intl.

MDW

Midway Intl.

$242 Roundtrip, found 4 days ago

$242

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Oct 3 from Tampa Intl. to Midway Intl., returning Sat, Oct 11, priced at $242 found 4 days ago

Fri, Aug 15 - Mon, Aug 18

SRQ

Sarasota-Bradenton Intl.

ORD

O'Hare Intl.

$282 Roundtrip, found 13 hours ago

$282

Roundtrip

found 13 hours ago

Select United flight, departing Fri, Aug 15 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $282 found 13 hours ago

Fri, Aug 15 - Mon, Aug 18

SRQ

Sarasota-Bradenton Intl.

ORD

O'Hare Intl.

$315 Roundtrip, found 13 hours ago

$315

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Fri, Aug 15 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $315 found 13 hours ago