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, Aug 14 - Thu, Aug 21

MCO

Orlando Intl.

ORD

O'Hare Intl.

$96 Roundtrip, found 6 days ago

$96

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Thu, Aug 14 from Orlando Intl. to O'Hare Intl., returning Thu, Aug 21, priced at $96 found 6 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$100 Roundtrip, found 10 hours ago

$100

Roundtrip

found 10 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 10 hours ago

Fri, Aug 15 - Mon, Aug 18

MCO

Orlando Intl.

ORD

O'Hare Intl.

$108 Roundtrip, found 6 days ago

$108

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Fri, Aug 15 from Orlando Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $108 found 6 days ago

Tue, Sep 2 - Fri, Sep 5

MCO

Orlando Intl.

ORD

O'Hare Intl.

$110 Roundtrip, found 10 hours ago

$110

Roundtrip

found 10 hours ago

Select Spirit Airlines flight, departing Tue, Sep 2 from Orlando Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $110 found 10 hours ago

Tue, Sep 16 - Sat, Sep 20

MCO

Orlando Intl.

ORD

O'Hare Intl.

$111 Roundtrip, found 21 hours ago

$111

Roundtrip

found 21 hours ago

Select Spirit Airlines flight, departing Tue, Sep 16 from Orlando Intl. to O'Hare Intl., returning Sat, Sep 20, priced at $111 found 21 hours ago

Fri, Sep 19 - Sat, Sep 20

MCO

Orlando Intl.

ORD

O'Hare Intl.

$113 Roundtrip, found 2 days ago

$113

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Fri, Sep 19 from Orlando Intl. to O'Hare Intl., returning Sat, Sep 20, priced at $113 found 2 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$119 Roundtrip, found 10 hours ago

$119

Roundtrip

found 10 hours ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $119 found 10 hours ago

Fri, Aug 15 - Mon, Aug 25

MCO

Orlando Intl.

ORD

O'Hare Intl.

$120 Roundtrip, found 21 hours ago

$120

Roundtrip

found 21 hours ago

Select Spirit Airlines flight, departing Fri, Aug 15 from Orlando Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $120 found 21 hours ago

Sat, Aug 16 - Fri, Aug 22

MCO

Orlando Intl.

ORD

O'Hare Intl.

$122 Roundtrip, found 21 hours ago

$122

Roundtrip

found 21 hours ago

Select Frontier Airlines flight, departing Sat, Aug 16 from Orlando Intl. to O'Hare Intl., returning Fri, Aug 22, priced at $122 found 21 hours ago

Fri, Aug 15 - Mon, Aug 25

MCO

Orlando Intl.

ORD

O'Hare Intl.

$124 Roundtrip, found 21 hours ago

$124

Roundtrip

found 21 hours ago

Select Frontier Airlines flight, departing Fri, Aug 15 from Orlando Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $124 found 21 hours ago

Thu, Aug 14 - Mon, Aug 18

MCO

Orlando Intl.

ORD

O'Hare Intl.

$128 Roundtrip, found 6 days ago

$128

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Thu, Aug 14 from Orlando Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $128 found 6 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$130 Roundtrip, found 10 hours ago

$130

Roundtrip

found 10 hours ago

Select American Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $130 found 10 hours ago

Sun, Sep 7 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$130 Roundtrip, found 10 hours ago

$130

Roundtrip

found 10 hours ago

Select Spirit Airlines flight, departing Sun, Sep 7 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $130 found 10 hours ago

Fri, Aug 15 - Mon, Aug 25

MCO

Orlando Intl.

ORD

O'Hare Intl.

$131 Roundtrip, found 21 hours ago

$131

Roundtrip

found 21 hours ago

Select Spirit Airlines flight, departing Fri, Aug 15 from Orlando Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $131 found 21 hours ago

Sun, Aug 17 - Mon, Aug 18

MCO

Orlando Intl.

MDW

Midway Intl.

$136 Roundtrip, found 6 days ago

$136

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sun, Aug 17 from Orlando Intl. to Midway Intl., returning Mon, Aug 18, priced at $136 found 6 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$138 Roundtrip, found 10 hours ago

$138

Roundtrip

found 10 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 10 hours ago

Tue, Sep 16 - Sat, Sep 20

MCO

Orlando Intl.

ORD

O'Hare Intl.

$157 Roundtrip, found 21 hours ago

$157

Roundtrip

found 21 hours ago

Select United flight, departing Tue, Sep 16 from Orlando Intl. to O'Hare Intl., returning Sat, Sep 20, priced at $157 found 21 hours ago

Tue, Sep 16 - Sat, Sep 20

MCO

Orlando Intl.

ORD

O'Hare Intl.

$157 Roundtrip, found 21 hours ago

$157

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Tue, Sep 16 from Orlando Intl. to O'Hare Intl., returning Sat, Sep 20, priced at $157 found 21 hours ago

Tue, Sep 16 - Sat, Sep 20

MCO

Orlando Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 21 hours ago

$197

Roundtrip

found 21 hours ago

Select Delta flight, departing Tue, Sep 16 from Orlando Intl. to O'Hare Intl., returning Sat, Sep 20, priced at $197 found 21 hours ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$315 Roundtrip, found 10 hours ago

$315

Roundtrip

found 10 hours ago

Select JetBlue Airways flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $315 found 10 hours ago