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.

Fri, May 23 - Sun, May 25

MCO

Orlando Intl.

MDW

Midway Intl.

$138 Roundtrip, found 1 day ago

$138

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Fri, May 23 from Orlando Intl. to Midway Intl., returning Sun, May 25, priced at $138 found 1 day ago

Thu, May 8 - Sat, May 10

MCO

Orlando Intl.

ORD

O'Hare Intl.

$144 Roundtrip, found 6 days ago

$144

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Thu, May 8 from Orlando Intl. to O'Hare Intl., returning Sat, May 10, priced at $144 found 6 days ago

Thu, May 22 - Sun, May 25

MCO

Orlando Intl.

MDW

Midway Intl.

$158 Roundtrip, found 1 day ago

$158

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, May 22 from Orlando Intl. to Midway Intl., returning Sun, May 25, priced at $158 found 1 day ago

Sun, May 4 - Sat, May 10

MCO

Orlando Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 6 days ago

$159

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sun, May 4 from Orlando Intl. to O'Hare Intl., returning Sat, May 10, priced at $159 found 6 days ago

Mon, May 19 - Sun, May 25

MCO

Orlando Intl.

MDW

Midway Intl.

$163 Roundtrip, found 1 day ago

$163

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, May 19 from Orlando Intl. to Midway Intl., returning Sun, May 25, priced at $163 found 1 day ago

Thu, May 22 - Mon, May 26

MCO

Orlando Intl.

MDW

Midway Intl.

$178 Roundtrip, found 1 day ago

$178

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, May 22 from Orlando Intl. to Midway Intl., returning Mon, May 26, priced at $178 found 1 day ago

Sat, May 3 - Sat, May 10

MCO

Orlando Intl.

ORD

O'Hare Intl.

$182 Roundtrip, found 6 days ago

$182

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, May 3 from Orlando Intl. to O'Hare Intl., returning Sat, May 10, priced at $182 found 6 days ago

Mon, May 19 - Mon, May 26

MCO

Orlando Intl.

MDW

Midway Intl.

$183 Roundtrip, found 1 day ago

$183

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, May 19 from Orlando Intl. to Midway Intl., returning Mon, May 26, priced at $183 found 1 day ago

Thu, May 22 - Fri, May 23

MCO

Orlando Intl.

MDW

Midway Intl.

$184 Roundtrip, found 1 day ago

$184

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, May 22 from Orlando Intl. to Midway Intl., returning Fri, May 23, priced at $184 found 1 day ago

Thu, May 8 - Wed, May 14

MCO

Orlando Intl.

ORD

O'Hare Intl.

$184 Roundtrip, found 6 days ago

$184

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Thu, May 8 from Orlando Intl. to O'Hare Intl., returning Wed, May 14, priced at $184 found 6 days ago

Mon, May 19 - Fri, May 23

MCO

Orlando Intl.

MDW

Midway Intl.

$189 Roundtrip, found 1 day ago

$189

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, May 19 from Orlando Intl. to Midway Intl., returning Fri, May 23, priced at $189 found 1 day ago

Sat, May 24 - Sun, May 25

MCO

Orlando Intl.

MDW

Midway Intl.

$193 Roundtrip, found 1 day ago

$193

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, May 24 from Orlando Intl. to Midway Intl., returning Sun, May 25, priced at $193 found 1 day ago

Thu, May 8 - Fri, May 9

MCO

Orlando Intl.

ORD

O'Hare Intl.

$198 Roundtrip, found 6 days ago

$198

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Thu, May 8 from Orlando Intl. to O'Hare Intl., returning Fri, May 9, priced at $198 found 6 days ago

Sat, May 24 - Sat, May 24

MCO

Orlando Intl.

MDW

Midway Intl.

$199 Roundtrip, found 1 day ago

$199

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, May 24 from Orlando Intl. to Midway Intl., returning Sat, May 24, priced at $199 found 1 day ago

Tue, May 6 - Wed, May 14

MCO

Orlando Intl.

ORD

O'Hare Intl.

$200 Roundtrip, found 6 days ago

$200

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Tue, May 6 from Orlando Intl. to O'Hare Intl., returning Wed, May 14, priced at $200 found 6 days ago

Sat, May 24 - Wed, May 28

MCO

Orlando Intl.

MDW

Midway Intl.

$208 Roundtrip, found 1 day ago

$208

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, May 24 from Orlando Intl. to Midway Intl., returning Wed, May 28, priced at $208 found 1 day ago

Sun, May 4 - Fri, May 9

MCO

Orlando Intl.

ORD

O'Hare Intl.

$213 Roundtrip, found 6 days ago

$213

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sun, May 4 from Orlando Intl. to O'Hare Intl., returning Fri, May 9, priced at $213 found 6 days ago

Wed, May 7 - Fri, May 9

MCO

Orlando Intl.

ORD

O'Hare Intl.

$214 Roundtrip, found 6 days ago

$214

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Wed, May 7 from Orlando Intl. to O'Hare Intl., returning Fri, May 9, priced at $214 found 6 days ago

Fri, May 23 - Tue, May 27

MCO

Orlando Intl.

MDW

Midway Intl.

$215 Roundtrip, found 1 day ago

$215

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Fri, May 23 from Orlando Intl. to Midway Intl., returning Tue, May 27, priced at $215 found 1 day ago

Sun, May 4 - Wed, May 14

MCO

Orlando Intl.

ORD

O'Hare Intl.

$216 Roundtrip, found 6 days ago

$216

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sun, May 4 from Orlando Intl. to O'Hare Intl., returning Wed, May 14, priced at $216 found 6 days ago