Flights from Chicago to Hilton Head Island

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, Jul 4 - Mon, Jul 7

MDW

Midway Intl.

SAV

Savannah - Hilton Head Intl.

$197 Roundtrip, found 1 day ago

$197

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Jul 4 from Midway Intl. to Savannah - Hilton Head Intl., returning Mon, Jul 7, priced at $197 found 1 day ago

Fri, Jul 25 - Fri, Aug 1

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$227 Roundtrip, found 4 days ago

$227

Roundtrip

found 4 days ago

Select American Airlines flight, departing Fri, Jul 25 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Fri, Aug 1, priced at $227 found 4 days ago

Fri, Jul 25 - Mon, Aug 4

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$227 Roundtrip, found 4 days ago

$227

Roundtrip

found 4 days ago

Select United flight, departing Fri, Jul 25 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Mon, Aug 4, priced at $227 found 4 days ago

Fri, Jul 4 - Fri, Jul 4

MDW

Midway Intl.

SAV

Savannah - Hilton Head Intl.

$248 Roundtrip, found 1 day ago

$248

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Jul 4 from Midway Intl. to Savannah - Hilton Head Intl., returning Fri, Jul 4, priced at $248 found 1 day ago

Wed, Jul 2 - Mon, Jul 7

MDW

Midway Intl.

SAV

Savannah - Hilton Head Intl.

$252 Roundtrip, found 1 day ago

$252

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jul 2 from Midway Intl. to Savannah - Hilton Head Intl., returning Mon, Jul 7, priced at $252 found 1 day ago

Tue, Jul 29 - Mon, Aug 4

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$254 Roundtrip, found 4 days ago

$254

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Mon, Aug 4, priced at $254 found 4 days ago

Fri, Jul 25 - Wed, Jul 30

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$289 Roundtrip, found 4 days ago

$289

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Fri, Jul 25 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Wed, Jul 30, priced at $289 found 4 days ago

Wed, Jul 23 - Fri, Aug 1

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$294 Roundtrip, found 4 days ago

$294

Roundtrip

found 4 days ago

Select American Airlines flight, departing Wed, Jul 23 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Fri, Aug 1, priced at $294 found 4 days ago

Sat, Jul 26 - Sat, Aug 2

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$301 Roundtrip, found 1 hour ago

$301

Roundtrip

found 1 hour ago

Select Delta flight, departing Sat, Jul 26 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Sat, Aug 2, priced at $301 found 1 hour ago

Sat, Jul 26 - Sat, Aug 2

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$302 Roundtrip, found 1 hour ago

$302

Roundtrip

found 1 hour ago

Select JetBlue Airways flight, departing Sat, Jul 26 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Sat, Aug 2, priced at $302 found 1 hour ago

Fri, Jul 25 - Thu, Jul 31

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$304 Roundtrip, found 4 days ago

$304

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Fri, Jul 25 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Thu, Jul 31, priced at $304 found 4 days ago

Thu, Jul 24 - Mon, Aug 4

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$307 Roundtrip, found 4 days ago

$307

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Jul 24 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Mon, Aug 4, priced at $307 found 4 days ago

Wed, Jul 2 - Tue, Jul 8

MDW

Midway Intl.

SAV

Savannah - Hilton Head Intl.

$309 Roundtrip, found 1 day ago

$309

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jul 2 from Midway Intl. to Savannah - Hilton Head Intl., returning Tue, Jul 8, priced at $309 found 1 day ago

Sat, Jul 26 - Sat, Aug 2

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$311 Roundtrip, found 1 hour ago

$311

Roundtrip

found 1 hour ago

Select American Airlines flight, departing Sat, Jul 26 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Sat, Aug 2, priced at $311 found 1 hour ago

Sat, Jul 26 - Sat, Aug 2

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$325 Roundtrip, found 1 hour ago

$325

Roundtrip

found 1 hour ago

Select Delta flight, departing Sat, Jul 26 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Sat, Aug 2, priced at $325 found 1 hour ago

Wed, Jul 2 - Sat, Jul 5

MDW

Midway Intl.

SAV

Savannah - Hilton Head Intl.

$328 Roundtrip, found 1 day ago

$328

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jul 2 from Midway Intl. to Savannah - Hilton Head Intl., returning Sat, Jul 5, priced at $328 found 1 day ago

Sat, Jul 26 - Sat, Aug 2

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$334 Roundtrip, found 1 hour ago

$334

Roundtrip

found 1 hour ago

Select American Airlines flight, departing Sat, Jul 26 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Sat, Aug 2, priced at $334 found 1 hour ago

Sat, Jul 26 - Sat, Aug 2

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$336 Roundtrip, found 1 hour ago

$336

Roundtrip

found 1 hour ago

Select Delta flight, departing Sat, Jul 26 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Sat, Aug 2, priced at $336 found 1 hour ago

Mon, Jun 30 - Thu, Jul 3

MDW

Midway Intl.

SAV

Savannah - Hilton Head Intl.

$339 Roundtrip, found 1 day ago

$339

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Jun 30 from Midway Intl. to Savannah - Hilton Head Intl., returning Thu, Jul 3, priced at $339 found 1 day ago

Sat, Jul 26 - Sat, Aug 2

ORD

O'Hare Intl.

SAV

Savannah - Hilton Head Intl.

$342 Roundtrip, found 1 hour ago

$342

Roundtrip

found 1 hour ago

Select JetBlue Airways flight, departing Sat, Jul 26 from O'Hare Intl. to Savannah - Hilton Head Intl., returning Sat, Aug 2, priced at $342 found 1 hour ago