Flights from Naples to Chicago

Cheapest flights from Naples

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, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$100 Roundtrip, found 3 days ago

$100

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $100 found 3 days ago

Mon, Sep 15 - Thu, Sep 18

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$110 Roundtrip, found 3 days ago

$110

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Mon, Sep 15 from Southwest Florida Intl. to O'Hare Intl., returning Thu, Sep 18, priced at $110 found 3 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$130 Roundtrip, found 3 days ago

$130

Roundtrip

found 3 days ago

Select United flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $130 found 3 days ago

Fri, Jul 18 - Mon, Jul 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$140 Roundtrip, found 6 days ago

$140

Roundtrip

found 6 days ago

Select United flight, departing Fri, Jul 18 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $140 found 6 days ago

Fri, Jul 18 - Mon, Jul 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$140 Roundtrip, found 6 days ago

$140

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Fri, Jul 18 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $140 found 6 days ago

Fri, Jul 18 - Mon, Jul 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 6 days ago

$159

Roundtrip

found 6 days ago

Select United flight, departing Fri, Jul 18 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $159 found 6 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 3 days ago

$159

Roundtrip

found 3 days ago

Select American Airlines flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $159 found 3 days ago

Fri, Jul 18 - Mon, Jul 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$169 Roundtrip, found 6 days ago

$169

Roundtrip

found 6 days ago

Select American Airlines flight, departing Fri, Jul 18 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $169 found 6 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$170 Roundtrip, found 3 days ago

$170

Roundtrip

found 3 days ago

Select United flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $170 found 3 days ago

Fri, Jul 18 - Mon, Jul 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$179 Roundtrip, found 6 days ago

$179

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Jul 18 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $179 found 6 days ago

Fri, Jul 18 - Mon, Jul 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$180 Roundtrip, found 6 days ago

$180

Roundtrip

found 6 days ago

Select United flight, departing Fri, Jul 18 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $180 found 6 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$180 Roundtrip, found 3 days ago

$180

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $180 found 3 days ago

Fri, Jul 18 - Mon, Jul 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$188 Roundtrip, found 6 days ago

$188

Roundtrip

found 6 days ago

Select American Airlines flight, departing Fri, Jul 18 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $188 found 6 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$192 Roundtrip, found 3 days ago

$192

Roundtrip

found 3 days ago

Select Sun Country Airlines flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $192 found 3 days ago

Fri, Jul 18 - Mon, Jul 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$200 Roundtrip, found 6 days ago

$200

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Fri, Jul 18 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $200 found 6 days ago

Fri, Jul 18 - Mon, Jul 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$206 Roundtrip, found 6 days ago

$206

Roundtrip

found 6 days ago

Select United flight, departing Fri, Jul 18 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $206 found 6 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

MDW

Midway Intl.

$307 Roundtrip, found 3 days ago

$307

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Sep 18 from Southwest Florida Intl. to Midway Intl., returning Sun, Sep 21, priced at $307 found 3 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

MDW

Midway Intl.

$379 Roundtrip, found 3 days ago

$379

Roundtrip

found 3 days ago

Select Delta flight, departing Thu, Sep 18 from Southwest Florida Intl. to Midway Intl., returning Sun, Sep 21, priced at $379 found 3 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$516 Roundtrip, found 3 days ago

$516

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $516 found 3 days ago

Fri, Jul 18 - Mon, Jul 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$11,654 Roundtrip, found 6 days ago

$11,654

Roundtrip

found 6 days ago

Select Alaska Airlines flight, departing Fri, Jul 18 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $11,654 found 6 days ago