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 4 days ago

$100

Roundtrip

found 4 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 4 days ago

Mon, Sep 15 - Thu, Sep 18

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$110 Roundtrip, found 4 days ago

$110

Roundtrip

found 4 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 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$130 Roundtrip, found 4 days ago

$130

Roundtrip

found 4 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 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 4 days ago

$159

Roundtrip

found 4 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 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$170 Roundtrip, found 4 days ago

$170

Roundtrip

found 4 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 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$180 Roundtrip, found 4 days ago

$180

Roundtrip

found 4 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 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$192 Roundtrip, found 4 days ago

$192

Roundtrip

found 4 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 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$210 Roundtrip, found 4 days ago

$210

Roundtrip

found 4 days ago

Select United flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $210 found 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$216 Roundtrip, found 4 days ago

$216

Roundtrip

found 4 days ago

Select United flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $216 found 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$218 Roundtrip, found 4 days ago

$218

Roundtrip

found 4 days ago

Select American Airlines flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $218 found 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$225 Roundtrip, found 4 days ago

$225

Roundtrip

found 4 days ago

Select American Airlines flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $225 found 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$230 Roundtrip, found 4 days ago

$230

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $230 found 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$234 Roundtrip, found 4 days ago

$234

Roundtrip

found 4 days ago

Select United flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $234 found 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$236 Roundtrip, found 4 days ago

$236

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $236 found 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

MDW

Midway Intl.

$307 Roundtrip, found 4 days ago

$307

Roundtrip

found 4 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 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$323 Roundtrip, found 4 days ago

$323

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Sep 18 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $323 found 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

MDW

Midway Intl.

$328 Roundtrip, found 4 days ago

$328

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Sep 18 from Southwest Florida Intl. to Midway Intl., returning Sun, Sep 21, priced at $328 found 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

MDW

Midway Intl.

$379 Roundtrip, found 4 days ago

$379

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Sep 18 from Southwest Florida Intl. to Midway Intl., returning Sun, Sep 21, priced at $379 found 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

MDW

Midway Intl.

$439 Roundtrip, found 4 days ago

$439

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Sep 18 from Southwest Florida Intl. to Midway Intl., returning Sun, Sep 21, priced at $439 found 4 days ago

Thu, Sep 18 - Sun, Sep 21

RSW

Southwest Florida Intl.

ORD

O'Hare Intl.

$516 Roundtrip, found 4 days ago

$516

Roundtrip

found 4 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 4 days ago