Flights from Chicago to Port Charlotte

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.

Thu, Jun 26 - Fri, Jul 4

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$150 Roundtrip, found 11 hours ago

$150

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Thu, Jun 26 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Jul 4, priced at $150 found 11 hours ago

Thu, Jun 26 - Mon, Jul 7

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$170 Roundtrip, found 11 hours ago

$170

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Thu, Jun 26 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 7, priced at $170 found 11 hours ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$179 Roundtrip, found 5 days ago

$179

Roundtrip

found 5 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 5 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$180 Roundtrip, found 5 days ago

$180

Roundtrip

found 5 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 5 days ago

Wed, Jul 2 - Mon, Jul 7

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$190 Roundtrip, found 11 hours ago

$190

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Wed, Jul 2 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 7, priced at $190 found 11 hours ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$197 Roundtrip, found 5 days ago

$197

Roundtrip

found 5 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 5 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$197 Roundtrip, found 5 days ago

$197

Roundtrip

found 5 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 5 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$197 Roundtrip, found 5 days ago

$197

Roundtrip

found 5 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 5 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$207 Roundtrip, found 5 days ago

$207

Roundtrip

found 5 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 5 days ago

Sat, Jun 14 - Thu, Jun 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$210 Roundtrip, found 11 hours ago

$210

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Jun 19, priced at $210 found 11 hours ago

Sat, Aug 16 - Sat, Aug 16

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$211 Roundtrip, found 5 days ago

$211

Roundtrip

found 5 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 5 days ago

Tue, Jul 1 - Tue, Jul 8

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$217 Roundtrip, found 11 hours ago

$217

Roundtrip

found 11 hours ago

Select Delta flight, departing Tue, Jul 1 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Jul 8, priced at $217 found 11 hours ago

Wed, Jun 25 - Sat, Jun 28

MDW

Midway Intl.

RSW

Southwest Florida Intl.

$227 Roundtrip, found 2 days ago

$227

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Jun 25 from Midway Intl. to Southwest Florida Intl., returning Sat, Jun 28, priced at $227 found 2 days ago

Sat, Jun 28 - Tue, Jul 8

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$227 Roundtrip, found 11 hours ago

$227

Roundtrip

found 11 hours ago

Select Delta flight, departing Sat, Jun 28 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Jul 8, priced at $227 found 11 hours ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$229 Roundtrip, found 5 days ago

$229

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, Aug 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Aug 18, priced at $229 found 5 days ago

Fri, Jun 13 - Thu, Jun 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$230 Roundtrip, found 11 hours ago

$230

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Fri, Jun 13 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Jun 19, priced at $230 found 11 hours ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$237 Roundtrip, found 5 days ago

$237

Roundtrip

found 5 days ago

Select United flight, departing Thu, Aug 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Aug 18, priced at $237 found 5 days ago

Thu, Jun 26 - Tue, Jul 8

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$240 Roundtrip, found 11 hours ago

$240

Roundtrip

found 11 hours ago

Select JetBlue Airways flight, departing Thu, Jun 26 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Jul 8, priced at $240 found 11 hours ago

Thu, Jun 12 - Sun, Jun 15

MDW

Midway Intl.

RSW

Southwest Florida Intl.

$240 Roundtrip, found 11 hours ago

$240

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Thu, Jun 12 from Midway Intl. to Southwest Florida Intl., returning Sun, Jun 15, priced at $240 found 11 hours ago

Tue, Jun 10 - Wed, Jun 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$11,654 Roundtrip, found 1 day ago

$11,654

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Tue, Jun 10 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Jun 18, priced at $11,654 found 1 day ago