Flights from Chicago to Okaloosa 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.

Thu, Jun 5 - Fri, Jun 6

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$782 Roundtrip, found 2 days ago

$782

Roundtrip

found 2 days ago

Select American Airlines flight, departing Thu, Jun 5 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Jun 6, priced at $782 found 2 days ago

Thu, Jun 5 - Thu, Jun 5

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$840 Roundtrip, found 2 days ago

$840

Roundtrip

found 2 days ago

Select American Airlines flight, departing Thu, Jun 5 from O'Hare Intl. to Northwest Florida Regional, returning Thu, Jun 5, priced at $840 found 2 days ago