Flights from Chicago to Fort Myers

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 6 days ago

$150

Roundtrip

found 6 days 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 6 days ago

Thu, Jun 26 - Mon, Jul 7

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$170 Roundtrip, found 6 days ago

$170

Roundtrip

found 6 days 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 6 days ago

Wed, Jun 18 - Thu, Jun 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$190 Roundtrip, found 1 day ago

$190

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Jun 26, priced at $190 found 1 day ago

Sun, Jun 22 - Thu, Jun 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$210 Roundtrip, found 1 day ago

$210

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Jun 22 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Jun 26, priced at $210 found 1 day ago

Tue, Jul 1 - Tue, Jul 8

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$217 Roundtrip, found 6 days ago

$217

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Jul 1 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Jul 8, priced at $217 found 6 days ago

Sat, Jun 28 - Tue, Jul 8

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$227 Roundtrip, found 6 days ago

$227

Roundtrip

found 6 days ago

Select Delta flight, departing Sat, Jun 28 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Jul 8, priced at $227 found 6 days ago

Thu, Jun 19 - Thu, Jun 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$230 Roundtrip, found 1 day ago

$230

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, Jun 19 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Jun 26, priced at $230 found 1 day ago

Thu, Jun 26 - Tue, Jul 8

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$240 Roundtrip, found 6 days ago

$240

Roundtrip

found 6 days 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 6 days ago

Wed, Jul 16 - Thu, Jul 31

MDW

Midway Intl.

RSW

Southwest Florida Intl.

$244 Roundtrip, found 4 days ago

$244

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Jul 16 from Midway Intl. to Southwest Florida Intl., returning Thu, Jul 31, priced at $244 found 4 days ago

Sun, Jun 29 - Tue, Jul 8

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$245 Roundtrip, found 6 days ago

$245

Roundtrip

found 6 days ago

Select United flight, departing Sun, Jun 29 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Jul 8, priced at $245 found 6 days ago

Fri, Jun 27 - Tue, Jul 8

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$247 Roundtrip, found 6 days ago

$247

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Jun 27 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Jul 8, priced at $247 found 6 days ago

Fri, Jun 13 - Mon, Jun 16

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$270 Roundtrip, found 6 days ago

$270

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Fri, Jun 13 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jun 16, priced at $270 found 6 days ago

Wed, Jul 16 - Thu, Jul 31

MDW

Midway Intl.

RSW

Southwest Florida Intl.

$284 Roundtrip, found 4 days ago

$284

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Jul 16 from Midway Intl. to Southwest Florida Intl., returning Thu, Jul 31, priced at $284 found 4 days ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$290 Roundtrip, found 6 days ago

$290

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Thu, Jun 12 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jun 16, priced at $290 found 6 days ago

Mon, Jun 23 - Tue, Jun 24

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$309 Roundtrip, found 1 day ago

$309

Roundtrip

found 1 day ago

Select United flight, departing Mon, Jun 23 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Jun 24, priced at $309 found 1 day ago

Wed, Jan 21 - Wed, Jan 28

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$314 Roundtrip, found 6 days ago

$314

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Jan 21 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Jan 28, priced at $314 found 6 days ago

Wed, Jul 16 - Thu, Jul 31

MDW

Midway Intl.

RSW

Southwest Florida Intl.

$315 Roundtrip, found 4 days ago

$315

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Jul 16 from Midway Intl. to Southwest Florida Intl., returning Thu, Jul 31, priced at $315 found 4 days ago

Wed, Jan 21 - Wed, Jan 28

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$320 Roundtrip, found 6 days ago

$320

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Wed, Jan 21 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Jan 28, priced at $320 found 6 days ago

Tue, Jun 17 - Fri, Jun 27

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$323 Roundtrip, found 1 day ago

$323

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jun 17 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Jun 27, priced at $323 found 1 day ago

Tue, Jun 17 - Mon, Jun 30

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$377 Roundtrip, found 1 day ago

$377

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jun 30, priced at $377 found 1 day ago