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.

Fri, Sep 19 - Fri, Sep 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$80 Roundtrip, found 6 days ago

$80

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Sep 26, priced at $80 found 6 days ago

Sun, Sep 21 - Sun, Sep 28

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$90 Roundtrip, found 3 days ago

$90

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sun, Sep 21 from O'Hare Intl. to Southwest Florida Intl., returning Sun, Sep 28, priced at $90 found 3 days ago

Tue, Aug 12 - Tue, Aug 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$109 Roundtrip, found 2 days ago

$109

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Aug 12 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Aug 19, priced at $109 found 2 days ago

Fri, Sep 19 - Fri, Sep 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$120 Roundtrip, found 6 days ago

$120

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Sep 26, priced at $120 found 6 days ago

Wed, Aug 13 - Tue, Aug 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$120 Roundtrip, found 2 days ago

$120

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Aug 13 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Aug 19, priced at $120 found 2 days ago

Fri, Sep 19 - Fri, Sep 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$132 Roundtrip, found 6 days ago

$132

Roundtrip

found 6 days ago

Select United flight, departing Fri, Sep 19 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Sep 26, priced at $132 found 6 days ago

Sun, Aug 10 - Tue, Aug 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$140 Roundtrip, found 2 days ago

$140

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sun, Aug 10 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Aug 19, priced at $140 found 2 days ago

Fri, Sep 19 - Fri, Sep 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$149 Roundtrip, found 6 days ago

$149

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Sep 19 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Sep 26, priced at $149 found 6 days ago

Wed, Aug 13 - Sat, Aug 16

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$150 Roundtrip, found 2 days ago

$150

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Aug 13 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Aug 16, priced at $150 found 2 days ago

Tue, Aug 12 - Tue, Aug 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$160 Roundtrip, found 2 days ago

$160

Roundtrip

found 2 days ago

Select United flight, departing Tue, Aug 12 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Aug 19, priced at $160 found 2 days ago

Tue, Aug 12 - Tue, Aug 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$164 Roundtrip, found 2 days ago

$164

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Aug 12 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Aug 19, priced at $164 found 2 days ago

Tue, Aug 12 - Tue, Aug 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$170 Roundtrip, found 2 days ago

$170

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Aug 12 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Aug 19, priced at $170 found 2 days ago

Sun, Aug 10 - 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 Sun, Aug 10 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Aug 16, priced at $170 found 2 days ago

Fri, Sep 19 - Fri, Sep 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$171 Roundtrip, found 6 days ago

$171

Roundtrip

found 6 days ago

Select United flight, departing Fri, Sep 19 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Sep 26, priced at $171 found 6 days ago

Fri, Sep 19 - Fri, Sep 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$171 Roundtrip, found 6 days ago

$171

Roundtrip

found 6 days ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Sep 26, priced at $171 found 6 days ago

Tue, Sep 16 - Tue, Sep 16

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$191 Roundtrip, found 3 days ago

$191

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Sep 16 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Tue, Sep 16, priced at $191 found 3 days ago

Sat, Sep 20 - Mon, Sep 29

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$211 Roundtrip, found 3 days ago

$211

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sat, Sep 20 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Sep 29, priced at $211 found 3 days ago

Mon, Nov 17 - Thu, Nov 27

MDW

Midway Intl.

RSW

Southwest Florida Intl.

$265 Roundtrip, found 21 hours ago

$265

Roundtrip

found 21 hours ago

Select Delta flight, departing Mon, Nov 17 from Midway Intl. to Southwest Florida Intl., returning Thu, Nov 27, priced at $265 found 21 hours ago

Sat, Aug 30 - Sat, Aug 30

MDW

Midway Intl.

SRQ

Sarasota-Bradenton Intl.

$297 Roundtrip, found 2 days ago

$297

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Aug 30 from Midway Intl. to Sarasota-Bradenton Intl., returning Sat, Aug 30, priced at $297 found 2 days ago

Tue, Aug 12 - Tue, Aug 19

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 Tue, Aug 12 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Aug 19, priced at $11,654 found 2 days ago