Flights from Chicago to Flagler Beach

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, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

MCO

Orlando Intl.

$110 Roundtrip, found 5 days ago

$110

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Orlando Intl., returning Sat, Sep 6, priced at $110 found 5 days ago

Thu, Sep 18 - Thu, Sep 25

ORD

O'Hare Intl.

MCO

Orlando Intl.

$120 Roundtrip, found 4 days ago

$120

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to Orlando Intl., returning Thu, Sep 25, priced at $120 found 4 days ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

MCO

Orlando Intl.

$129 Roundtrip, found 5 days ago

$129

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Orlando Intl., returning Sat, Sep 6, priced at $129 found 5 days ago

Tue, Aug 5 - Fri, Aug 15

ORD

O'Hare Intl.

MCO

Orlando Intl.

$130 Roundtrip, found 2 days ago

$130

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Orlando Intl., returning Fri, Aug 15, priced at $130 found 2 days ago

Thu, Jun 26 - Sun, Jun 29

ORD

O'Hare Intl.

MCO

Orlando Intl.

$138 Roundtrip, found 6 days ago

$138

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Thu, Jun 26 from O'Hare Intl. to Orlando Intl., returning Sun, Jun 29, priced at $138 found 6 days ago

Mon, Jul 14 - Fri, Jul 18

MDW

Midway Intl.

MCO

Orlando Intl.

$138 Roundtrip, found 3 days ago

$138

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Mon, Jul 14 from Midway Intl. to Orlando Intl., returning Fri, Jul 18, priced at $138 found 3 days ago

Wed, Jun 25 - Tue, Jul 1

ORD

O'Hare Intl.

MCO

Orlando Intl.

$138 Roundtrip, found 13 hours ago

$138

Roundtrip

found 13 hours ago

Select Frontier Airlines flight, departing Wed, Jun 25 from O'Hare Intl. to Orlando Intl., returning Tue, Jul 1, priced at $138 found 13 hours ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

MCO

Orlando Intl.

$139 Roundtrip, found 5 days ago

$139

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Orlando Intl., returning Sat, Sep 6, priced at $139 found 5 days ago

Thu, Jun 26 - Tue, Jul 1

ORD

O'Hare Intl.

MCO

Orlando Intl.

$140 Roundtrip, found 13 hours ago

$140

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Thu, Jun 26 from O'Hare Intl. to Orlando Intl., returning Tue, Jul 1, priced at $140 found 13 hours ago

Wed, Jun 25 - Sat, Jul 5

ORD

O'Hare Intl.

MCO

Orlando Intl.

$143 Roundtrip, found 13 hours ago

$143

Roundtrip

found 13 hours ago

Select Frontier Airlines flight, departing Wed, Jun 25 from O'Hare Intl. to Orlando Intl., returning Sat, Jul 5, priced at $143 found 13 hours ago

Tue, Jul 15 - Tue, Jul 22

ORD

O'Hare Intl.

MCO

Orlando Intl.

$144 Roundtrip, found 2 days ago

$144

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Tue, Jul 15 from O'Hare Intl. to Orlando Intl., returning Tue, Jul 22, priced at $144 found 2 days ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

MCO

Orlando Intl.

$148 Roundtrip, found 5 days ago

$148

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Orlando Intl., returning Sat, Sep 6, priced at $148 found 5 days ago

Wed, Jun 25 - Thu, Jul 3

ORD

O'Hare Intl.

MCO

Orlando Intl.

$149 Roundtrip, found 13 hours ago

$149

Roundtrip

found 13 hours ago

Select Frontier Airlines flight, departing Wed, Jun 25 from O'Hare Intl. to Orlando Intl., returning Thu, Jul 3, priced at $149 found 13 hours ago

Thu, Sep 18 - Sat, Sep 27

ORD

O'Hare Intl.

MCO

Orlando Intl.

$150 Roundtrip, found 4 days ago

$150

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to Orlando Intl., returning Sat, Sep 27, priced at $150 found 4 days ago

Tue, Jul 15 - Tue, Jul 22

ORD

O'Hare Intl.

MCO

Orlando Intl.

$157 Roundtrip, found 2 days ago

$157

Roundtrip

found 2 days ago

Select United flight, departing Tue, Jul 15 from O'Hare Intl. to Orlando Intl., returning Tue, Jul 22, priced at $157 found 2 days ago

Tue, Sep 9 - Wed, Sep 17

ORD

O'Hare Intl.

MCO

Orlando Intl.

$157 Roundtrip, found 4 days ago

$157

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Sep 9 from O'Hare Intl. to Orlando Intl., returning Wed, Sep 17, priced at $157 found 4 days ago

Tue, Aug 19 - Tue, Aug 19

MDW

Midway Intl.

MCO

Orlando Intl.

$191 Roundtrip, found 4 days ago

$191

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Aug 19 from Midway Intl. to Orlando Intl., returning Tue, Aug 19, priced at $191 found 4 days ago

Fri, Jun 13 - Sun, Jun 15

MDW

Midway Intl.

JAX

Jacksonville Intl.

$222 Roundtrip, found 1 day ago

$222

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Fri, Jun 13 from Midway Intl. to Jacksonville Intl., returning Sun, Jun 15, priced at $222 found 1 day ago

Thu, Jun 12 - Thu, Jun 19

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$226 Roundtrip, found 1 day ago

$226

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Jun 12 from O'Hare Intl. to Jacksonville Intl., returning Thu, Jun 19, priced at $226 found 1 day ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

MCO

Orlando Intl.

$268 Roundtrip, found 5 days ago

$268

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Fri, Sep 5 from O'Hare Intl. to Orlando Intl., returning Sat, Sep 6, priced at $268 found 5 days ago