Flights from Chicago to Tropical Gulf Acres

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, Oct 18 - Wed, Oct 22

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$146 Roundtrip, found 4 days ago

$146

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Oct 22, priced at $146 found 4 days ago

Sat, Oct 18 - Wed, Oct 22

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$152 Roundtrip, found 4 days ago

$152

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Oct 22, priced at $152 found 4 days ago

Wed, Oct 15 - Wed, Oct 22

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$156 Roundtrip, found 4 days ago

$156

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Oct 22, priced at $156 found 4 days ago

Mon, Aug 11 - Sat, Aug 16

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$170 Roundtrip, found 2 days ago

$170

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Aug 11 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Aug 16, priced at $170 found 2 days ago

Wed, Oct 15 - Tue, Oct 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$176 Roundtrip, found 4 days ago

$176

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Oct 21, priced at $176 found 4 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$179 Roundtrip, found 2 days ago

$179

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Aug 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Aug 18, priced at $179 found 2 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$180 Roundtrip, found 2 days ago

$180

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Aug 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Aug 18, priced at $180 found 2 days ago

Sat, Oct 18 - Wed, Oct 22

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$182 Roundtrip, found 4 days ago

$182

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Oct 18 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Oct 22, priced at $182 found 4 days ago

Mon, Aug 11 - Tue, Aug 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$190 Roundtrip, found 2 days ago

$190

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Aug 11 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Aug 19, priced at $190 found 2 days ago

Thu, Oct 16 - Mon, Oct 20

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$192 Roundtrip, found 4 days ago

$192

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Oct 20, priced at $192 found 4 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$196 Roundtrip, found 4 days ago

$196

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Oct 20, priced at $196 found 4 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$197 Roundtrip, found 2 days ago

$197

Roundtrip

found 2 days ago

Select United flight, departing Thu, Aug 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Aug 18, priced at $197 found 2 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$197 Roundtrip, found 2 days ago

$197

Roundtrip

found 2 days ago

Select United flight, departing Thu, Aug 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Aug 18, priced at $197 found 2 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$197 Roundtrip, found 2 days ago

$197

Roundtrip

found 2 days ago

Select American Airlines flight, departing Thu, Aug 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Aug 18, priced at $197 found 2 days ago

Sat, Oct 18 - Wed, Oct 22

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$202 Roundtrip, found 4 days ago

$202

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Oct 22, priced at $202 found 4 days ago

Thu, Oct 16 - Mon, Oct 20

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$206 Roundtrip, found 4 days ago

$206

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Oct 20, priced at $206 found 4 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$207 Roundtrip, found 2 days ago

$207

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Aug 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Aug 18, priced at $207 found 2 days ago

Sat, Aug 16 - Sat, Aug 16

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$211 Roundtrip, found 2 days ago

$211

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Aug 16 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Aug 16, priced at $211 found 2 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$304 Roundtrip, found 2 days ago

$304

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Thu, Aug 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Aug 18, priced at $304 found 2 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$11,654 Roundtrip, found 2 days ago

$11,654

Roundtrip

found 2 days ago

Select Alaska Airlines flight, departing Thu, Aug 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Aug 18, priced at $11,654 found 2 days ago