Flights from Orlando to Chicago

Cheapest flights from Orlando

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.

Wed, Sep 3 - Fri, Sep 5

MCO

Orlando Intl.

ORD

O'Hare Intl.

$106 Roundtrip, just found

$106

Roundtrip

just found

Select Spirit Airlines flight, departing Wed, Sep 3 from Orlando Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $106 just found

Mon, Sep 1 - Thu, Sep 4

MCO

Orlando Intl.

ORD

O'Hare Intl.

$116 Roundtrip, found 4 days ago

$116

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Mon, Sep 1 from Orlando Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $116 found 4 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$126 Roundtrip, found 5 hours ago

$126

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $126 found 5 hours ago

Wed, Aug 6 - Mon, Aug 11

MCO

Orlando Intl.

ORD

O'Hare Intl.

$131 Roundtrip, found 5 days ago

$131

Roundtrip

found 5 days ago

Select United flight, departing Wed, Aug 6 from Orlando Intl. to O'Hare Intl., returning Mon, Aug 11, priced at $131 found 5 days ago

Wed, Aug 6 - Mon, Aug 11

MCO

Orlando Intl.

ORD

O'Hare Intl.

$131 Roundtrip, found 5 days ago

$131

Roundtrip

found 5 days ago

Select American Airlines flight, departing Wed, Aug 6 from Orlando Intl. to O'Hare Intl., returning Mon, Aug 11, priced at $131 found 5 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$133 Roundtrip, found 5 hours ago

$133

Roundtrip

found 5 hours ago

Select United flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $133 found 5 hours ago

Wed, Sep 3 - Fri, Sep 5

MCO

Orlando Intl.

ORD

O'Hare Intl.

$135 Roundtrip, just found

$135

Roundtrip

just found

Select Spirit Airlines flight, departing Wed, Sep 3 from Orlando Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $135 just found

Sat, Aug 30 - Thu, Sep 4

MCO

Orlando Intl.

ORD

O'Hare Intl.

$136 Roundtrip, found 4 days ago

$136

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Aug 30 from Orlando Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $136 found 4 days ago

Wed, Sep 3 - Fri, Sep 5

MCO

Orlando Intl.

ORD

O'Hare Intl.

$137 Roundtrip, just found

$137

Roundtrip

just found

Select United flight, departing Wed, Sep 3 from Orlando Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $137 just found

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$140 Roundtrip, found 5 hours ago

$140

Roundtrip

found 5 hours ago

Select Frontier Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $140 found 5 hours ago

Tue, Sep 2 - Sun, Sep 7

MCO

Orlando Intl.

ORD

O'Hare Intl.

$143 Roundtrip, found 4 days ago

$143

Roundtrip

found 4 days ago

Select United flight, departing Tue, Sep 2 from Orlando Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $143 found 4 days ago

Wed, Sep 3 - Fri, Sep 5

MCO

Orlando Intl.

ORD

O'Hare Intl.

$144 Roundtrip, just found

$144

Roundtrip

just found

Select Spirit Airlines flight, departing Wed, Sep 3 from Orlando Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $144 just found

Wed, Sep 3 - Fri, Sep 5

MCO

Orlando Intl.

ORD

O'Hare Intl.

$152 Roundtrip, just found

$152

Roundtrip

just found

Select Delta flight, departing Wed, Sep 3 from Orlando Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $152 just found

Wed, Aug 6 - Mon, Aug 11

MCO

Orlando Intl.

ORD

O'Hare Intl.

$152 Roundtrip, found 5 days ago

$152

Roundtrip

found 5 days ago

Select United flight, departing Wed, Aug 6 from Orlando Intl. to O'Hare Intl., returning Mon, Aug 11, priced at $152 found 5 days ago

Wed, Aug 6 - Mon, Aug 11

MCO

Orlando Intl.

ORD

O'Hare Intl.

$154 Roundtrip, found 5 days ago

$154

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Aug 6 from Orlando Intl. to O'Hare Intl., returning Mon, Aug 11, priced at $154 found 5 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$157 Roundtrip, found 5 hours ago

$157

Roundtrip

found 5 hours ago

Select Delta flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $157 found 5 hours ago

Fri, Aug 8 - Thu, Aug 14

MCO

Orlando Intl.

ORD

O'Hare Intl.

$158 Roundtrip, found 5 days ago

$158

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Aug 8 from Orlando Intl. to O'Hare Intl., returning Thu, Aug 14, priced at $158 found 5 days ago

Sun, Aug 31 - Sat, Sep 6

MCO

Orlando Intl.

ORD

O'Hare Intl.

$158 Roundtrip, found 4 days ago

$158

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sun, Aug 31 from Orlando Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $158 found 4 days ago

Wed, Sep 3 - Fri, Sep 5

MCO

Orlando Intl.

ORD

O'Hare Intl.

$248 Roundtrip, just found

$248

Roundtrip

just found

Select Delta flight, departing Wed, Sep 3 from Orlando Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $248 just found

Wed, Sep 3 - Fri, Sep 5

MCO

Orlando Intl.

ORD

O'Hare Intl.

$268 Roundtrip, just found

$268

Roundtrip

just found

Select JetBlue Airways flight, departing Wed, Sep 3 from Orlando Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $268 just found