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.

Thu, Sep 4 - Sun, Sep 7

MCO

Orlando Intl.

ORD

O'Hare Intl.

$98 Roundtrip, found 6 days ago

$98

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Thu, Sep 4 from Orlando Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $98 found 6 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$100 Roundtrip, found 1 day ago

$100

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $100 found 1 day ago

Thu, Sep 4 - Fri, Sep 5

MCO

Orlando Intl.

ORD

O'Hare Intl.

$104 Roundtrip, found 6 days ago

$104

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Thu, Sep 4 from Orlando Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $104 found 6 days ago

Sun, Sep 7 - Thu, Sep 11

MCO

Orlando Intl.

ORD

O'Hare Intl.

$110 Roundtrip, found 6 days ago

$110

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sun, Sep 7 from Orlando Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $110 found 6 days ago

Wed, Jul 23 - Wed, Jul 30

MCO

Orlando Intl.

ORD

O'Hare Intl.

$119 Roundtrip, found 5 days ago

$119

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Wed, Jul 23 from Orlando Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $119 found 5 days ago

Sat, Jul 26 - Mon, Jul 28

MCO

Orlando Intl.

MDW

Midway Intl.

$119 Roundtrip, found 5 days ago

$119

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sat, Jul 26 from Orlando Intl. to Midway Intl., returning Mon, Jul 28, priced at $119 found 5 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$120 Roundtrip, found 1 day ago

$120

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $120 found 1 day ago

Mon, Jul 28 - Thu, Jul 31

MCO

Orlando Intl.

MDW

Midway Intl.

$128 Roundtrip, found 5 days ago

$128

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Mon, Jul 28 from Orlando Intl. to Midway Intl., returning Thu, Jul 31, priced at $128 found 5 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$130 Roundtrip, found 1 day ago

$130

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $130 found 1 day ago

Tue, Jul 29 - Wed, Jul 30

MCO

Orlando Intl.

ORD

O'Hare Intl.

$130 Roundtrip, found 5 days ago

$130

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Jul 29 from Orlando Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $130 found 5 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$134 Roundtrip, found 1 day ago

$134

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $134 found 1 day ago

Mon, Jul 28 - Sun, Aug 3

MCO

Orlando Intl.

MDW

Midway Intl.

$137 Roundtrip, found 5 days ago

$137

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Mon, Jul 28 from Orlando Intl. to Midway Intl., returning Sun, Aug 3, priced at $137 found 5 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$138 Roundtrip, found 1 day ago

$138

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $138 found 1 day ago

Sun, Jul 27 - Thu, Jul 31

MCO

Orlando Intl.

MDW

Midway Intl.

$139 Roundtrip, found 5 days ago

$139

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sun, Jul 27 from Orlando Intl. to Midway Intl., returning Thu, Jul 31, priced at $139 found 5 days ago

Mon, Sep 29 - Fri, Oct 17

MCO

Orlando Intl.

ORD

O'Hare Intl.

$140 Roundtrip, found 1 day ago

$140

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Sep 29 from Orlando Intl. to O'Hare Intl., returning Fri, Oct 17, priced at $140 found 1 day ago

Wed, Jul 16 - Tue, Jul 22

MCO

Orlando Intl.

ORD

O'Hare Intl.

$145 Roundtrip, found 2 days ago

$145

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Wed, Jul 16 from Orlando Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $145 found 2 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 1 day ago

$159

Roundtrip

found 1 day ago

Select United flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $159 found 1 day ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 1 day ago

$159

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $159 found 1 day ago

Tue, Jul 29 - Tue, Jul 29

MCO

Orlando Intl.

MDW

Midway Intl.

$193 Roundtrip, found 5 days ago

$193

Roundtrip

found 5 days ago

Select Delta flight, departing Tue, Jul 29 from Orlando Intl. to Midway Intl., returning Tue, Jul 29, priced at $193 found 5 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$217 Roundtrip, found 1 day ago

$217

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $217 found 1 day ago