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 11 hours ago

$98

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Thu, Sep 4 from Orlando Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $98 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$99 Roundtrip, found 11 hours ago

$99

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $99 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$100 Roundtrip, found 11 hours ago

$100

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $100 found 11 hours ago

Thu, Sep 4 - Fri, Sep 5

MCO

Orlando Intl.

ORD

O'Hare Intl.

$104 Roundtrip, found 11 hours ago

$104

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Thu, Sep 4 from Orlando Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $104 found 11 hours ago

Sun, Sep 7 - Thu, Sep 11

MCO

Orlando Intl.

ORD

O'Hare Intl.

$110 Roundtrip, found 11 hours ago

$110

Roundtrip

found 11 hours ago

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

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$125 Roundtrip, found 11 hours ago

$125

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $125 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$129 Roundtrip, found 11 hours ago

$129

Roundtrip

found 11 hours ago

Select American Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $129 found 11 hours ago

Tue, Sep 2 - Sun, Sep 7

MCO

Orlando Intl.

ORD

O'Hare Intl.

$130 Roundtrip, found 11 hours ago

$130

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Tue, Sep 2 from Orlando Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $130 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$133 Roundtrip, found 11 hours ago

$133

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $133 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$134 Roundtrip, found 11 hours ago

$134

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $134 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 11 hours ago

$137

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $137 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$138 Roundtrip, found 11 hours ago

$138

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $138 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$139 Roundtrip, found 11 hours ago

$139

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $139 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$147 Roundtrip, found 11 hours ago

$147

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $147 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$149 Roundtrip, found 11 hours ago

$149

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $149 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 11 hours ago

$159

Roundtrip

found 11 hours ago

Select United flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $159 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 11 hours ago

$159

Roundtrip

found 11 hours ago

Select American Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $159 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$217 Roundtrip, found 11 hours ago

$217

Roundtrip

found 11 hours ago

Select JetBlue Airways flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $217 found 11 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$238 Roundtrip, found 11 hours ago

$238

Roundtrip

found 11 hours ago

Select Delta flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $238 found 11 hours ago

Sun, Jul 6 - Mon, Jul 14

MCO

Orlando Intl.

MDW

Midway Intl.

$287 Roundtrip, found 1 day ago

$287

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sun, Jul 6 from Orlando Intl. to Midway Intl., returning Mon, Jul 14, priced at $287 found 1 day ago