Flights from Chicago to Homeland

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.

Tue, Aug 5 - Fri, Aug 15

ORD

O'Hare Intl.

MCO

Orlando Intl.

$130 Roundtrip, found 1 day ago

$130

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Orlando Intl., returning Fri, Aug 15, priced at $130 found 1 day ago

Sat, Aug 2 - Sat, Aug 9

ORD

O'Hare Intl.

MCO

Orlando Intl.

$135 Roundtrip, found 4 days ago

$135

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Orlando Intl., returning Sat, Aug 9, priced at $135 found 4 days ago

Tue, Aug 5 - Fri, Aug 15

ORD

O'Hare Intl.

MCO

Orlando Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select United flight, departing Tue, Aug 5 from O'Hare Intl. to Orlando Intl., returning Fri, Aug 15, priced at $137 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

MCO

Orlando Intl.

$138 Roundtrip, found 2 days ago

$138

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Mon, Sep 29 from O'Hare Intl. to Orlando Intl., returning Fri, Oct 3, priced at $138 found 2 days ago

Mon, Jul 14 - Sun, Jul 27

ORD

O'Hare Intl.

MCO

Orlando Intl.

$140 Roundtrip, found 2 hours ago

$140

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Orlando Intl., returning Sun, Jul 27, priced at $140 found 2 hours ago

Tue, Aug 5 - Fri, Aug 15

ORD

O'Hare Intl.

MCO

Orlando Intl.

$143 Roundtrip, found 1 day ago

$143

Roundtrip

found 1 day ago

Select United flight, departing Tue, Aug 5 from O'Hare Intl. to Orlando Intl., returning Fri, Aug 15, priced at $143 found 1 day ago

Tue, Aug 5 - Fri, Aug 15

ORD

O'Hare Intl.

MCO

Orlando Intl.

$143 Roundtrip, found 1 day ago

$143

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Orlando Intl., returning Fri, Aug 15, priced at $143 found 1 day ago

Wed, Jun 25 - Thu, Jul 3

ORD

O'Hare Intl.

MCO

Orlando Intl.

$149 Roundtrip, found 5 days ago

$149

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Wed, Jun 25 from O'Hare Intl. to Orlando Intl., returning Thu, Jul 3, priced at $149 found 5 days ago

Mon, Jun 30 - Sat, Jul 5

ORD

O'Hare Intl.

MCO

Orlando Intl.

$154 Roundtrip, found 5 days ago

$154

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Mon, Jun 30 from O'Hare Intl. to Orlando Intl., returning Sat, Jul 5, priced at $154 found 5 days ago

Sun, Jun 29 - Thu, Jul 3

MDW

Midway Intl.

MCO

Orlando Intl.

$159 Roundtrip, found 5 days ago

$159

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sun, Jun 29 from Midway Intl. to Orlando Intl., returning Thu, Jul 3, priced at $159 found 5 days ago

Sat, Aug 2 - Sat, Aug 9

ORD

O'Hare Intl.

MCO

Orlando Intl.

$160 Roundtrip, found 4 days ago

$160

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 2 from O'Hare Intl. to Orlando Intl., returning Sat, Aug 9, priced at $160 found 4 days ago

Tue, Aug 5 - Fri, Aug 15

ORD

O'Hare Intl.

MCO

Orlando Intl.

$164 Roundtrip, found 1 day ago

$164

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Orlando Intl., returning Fri, Aug 15, priced at $164 found 1 day ago

Wed, Jul 30 - Sat, Aug 9

ORD

O'Hare Intl.

MCO

Orlando Intl.

$164 Roundtrip, found 4 days ago

$164

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Wed, Jul 30 from O'Hare Intl. to Orlando Intl., returning Sat, Aug 9, priced at $164 found 4 days ago

Thu, Jul 31 - Sat, Aug 9

ORD

O'Hare Intl.

MCO

Orlando Intl.

$165 Roundtrip, found 4 days ago

$165

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Jul 31 from O'Hare Intl. to Orlando Intl., returning Sat, Aug 9, priced at $165 found 4 days ago

Tue, Aug 5 - Fri, Aug 15

ORD

O'Hare Intl.

MCO

Orlando Intl.

$167 Roundtrip, found 1 day ago

$167

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Orlando Intl., returning Fri, Aug 15, priced at $167 found 1 day ago

Tue, Aug 5 - Fri, Aug 15

ORD

O'Hare Intl.

MCO

Orlando Intl.

$168 Roundtrip, found 1 day ago

$168

Roundtrip

found 1 day ago

Select United flight, departing Tue, Aug 5 from O'Hare Intl. to Orlando Intl., returning Fri, Aug 15, priced at $168 found 1 day ago

Tue, Aug 5 - Fri, Aug 15

ORD

O'Hare Intl.

MCO

Orlando Intl.

$168 Roundtrip, found 1 day ago

$168

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Orlando Intl., returning Fri, Aug 15, priced at $168 found 1 day ago

Thu, Jul 17 - Sun, Jul 27

ORD

O'Hare Intl.

MCO

Orlando Intl.

$170 Roundtrip, found 2 hours ago

$170

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Thu, Jul 17 from O'Hare Intl. to Orlando Intl., returning Sun, Jul 27, priced at $170 found 2 hours ago

Sat, Jun 28 - Fri, Jul 4

MDW

Midway Intl.

MCO

Orlando Intl.

$217 Roundtrip, found 5 days ago

$217

Roundtrip

found 5 days ago

Select Delta flight, departing Sat, Jun 28 from Midway Intl. to Orlando Intl., returning Fri, Jul 4, priced at $217 found 5 days ago

Tue, Jun 24 - Fri, Jul 4

ORD

O'Hare Intl.

MCO

Orlando Intl.

$363 Roundtrip, found 2 days ago

$363

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Tue, Jun 24 from O'Hare Intl. to Orlando Intl., returning Fri, Jul 4, priced at $363 found 2 days ago