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.

Wed, Jul 16 - Sat, Jul 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$120 Roundtrip, found 7 hours ago

$120

Roundtrip

found 7 hours ago

Select Spirit Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Jul 19, priced at $120 found 7 hours ago

Mon, Jul 14 - Mon, Jul 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$130 Roundtrip, found 7 hours ago

$130

Roundtrip

found 7 hours ago

Select Spirit Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $130 found 7 hours ago

Wed, Jul 16 - Fri, Jul 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$140 Roundtrip, found 7 hours ago

$140

Roundtrip

found 7 hours ago

Select Spirit Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Jul 18, priced at $140 found 7 hours ago

Mon, Jul 14 - Mon, Jul 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$155 Roundtrip, found 7 hours ago

$155

Roundtrip

found 7 hours ago

Select American Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $155 found 7 hours ago

Sun, Jul 13 - Sat, Jul 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$160 Roundtrip, found 7 hours ago

$160

Roundtrip

found 7 hours ago

Select Spirit Airlines flight, departing Sun, Jul 13 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Jul 19, priced at $160 found 7 hours ago

Mon, Jul 14 - Mon, Jul 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$164 Roundtrip, found 7 hours ago

$164

Roundtrip

found 7 hours ago

Select Spirit Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $164 found 7 hours ago

Mon, Jul 14 - Mon, Jul 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$178 Roundtrip, found 7 hours ago

$178

Roundtrip

found 7 hours ago

Select American Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $178 found 7 hours ago

Sun, Jul 13 - Fri, Jul 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$180 Roundtrip, found 7 hours ago

$180

Roundtrip

found 7 hours ago

Select Spirit Airlines flight, departing Sun, Jul 13 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Jul 18, priced at $180 found 7 hours ago

Mon, Jul 14 - Mon, Jul 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$188 Roundtrip, found 7 hours ago

$188

Roundtrip

found 7 hours ago

Select United flight, departing Mon, Jul 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $188 found 7 hours ago

Mon, Jul 14 - Mon, Jul 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$188 Roundtrip, found 7 hours ago

$188

Roundtrip

found 7 hours ago

Select American Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $188 found 7 hours ago

Mon, Jun 23 - Mon, Jun 30

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$190 Roundtrip, found 7 hours ago

$190

Roundtrip

found 7 hours ago

Select Spirit Airlines flight, departing Mon, Jun 23 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jun 30, priced at $190 found 7 hours ago

Mon, Jul 14 - Mon, Jul 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$195 Roundtrip, found 7 hours ago

$195

Roundtrip

found 7 hours ago

Select United flight, departing Mon, Jul 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $195 found 7 hours ago

Fri, Jun 20 - Thu, Jul 3

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$200 Roundtrip, found 7 hours ago

$200

Roundtrip

found 7 hours ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Jul 3, priced at $200 found 7 hours ago

Sun, Jun 22 - Thu, Jun 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$210 Roundtrip, found 3 days ago

$210

Roundtrip

found 3 days 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 3 days ago

Mon, Jul 14 - Mon, Jul 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$211 Roundtrip, found 7 hours ago

$211

Roundtrip

found 7 hours ago

Select American Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $211 found 7 hours ago

Wed, Jul 16 - Thu, Jul 31

MDW

Midway Intl.

RSW

Southwest Florida Intl.

$244 Roundtrip, found 6 days ago

$244

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Jul 16 from Midway Intl. to Southwest Florida Intl., returning Thu, Jul 31, priced at $244 found 6 days ago

Thu, Jun 26 - Tue, Jul 1

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$293 Roundtrip, found 7 hours ago

$293

Roundtrip

found 7 hours ago

Select Delta flight, departing Thu, Jun 26 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Jul 1, priced at $293 found 7 hours ago

Mon, Jul 14 - Mon, Jul 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$356 Roundtrip, found 7 hours ago

$356

Roundtrip

found 7 hours ago

Select JetBlue Airways flight, departing Mon, Jul 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $356 found 7 hours ago

Sun, Jun 22 - Sun, Jun 29

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$508 Roundtrip, found 7 hours ago

$508

Roundtrip

found 7 hours ago

Select Frontier Airlines flight, departing Sun, Jun 22 from O'Hare Intl. to Southwest Florida Intl., returning Sun, Jun 29, priced at $508 found 7 hours ago

Mon, Jul 14 - Mon, Jul 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$11,654 Roundtrip, found 7 hours ago

$11,654

Roundtrip

found 7 hours ago

Select Alaska Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $11,654 found 7 hours ago