Cheapest flights from Chicago
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, May 22 - Thu, May 23
MDW
Midway Intl.
MCO
Orlando Intl.
$78 Roundtrip, found 2 days ago
$78
Roundtrip
found 2 days ago
Tue, Apr 30 - Wed, May 1
ORD
O'Hare Intl.
MCO
Orlando Intl.
$79 Roundtrip, found 3 days ago
$79
Roundtrip
found 3 days ago
Tue, Apr 30 - Wed, May 8
ORD
O'Hare Intl.
MCO
Orlando Intl.
$85 Roundtrip, found 3 days ago
$85
Roundtrip
found 3 days ago
Sun, May 26 - Tue, Jun 4
ORD
O'Hare Intl.
MCO
Orlando Intl.
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
Tue, Apr 30 - Tue, Apr 30
ORD
O'Hare Intl.
MCO
Orlando Intl.
$87 Roundtrip, found 3 days ago
$87
Roundtrip
found 3 days ago
Mon, Apr 29 - Fri, May 3
ORD
O'Hare Intl.
MCO
Orlando Intl.
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Tue, Apr 30 - Sat, May 4
ORD
O'Hare Intl.
MCO
Orlando Intl.
$90 Roundtrip, found 3 days ago
$90
Roundtrip
found 3 days ago
Sat, Apr 27 - Wed, May 1
ORD
O'Hare Intl.
MCO
Orlando Intl.
$91 Roundtrip, found 3 days ago
$91
Roundtrip
found 3 days ago
Wed, May 1 - Wed, May 8
ORD
O'Hare Intl.
MCO
Orlando Intl.
$93 Roundtrip, found 3 days ago
$93
Roundtrip
found 3 days ago
Mon, Apr 29 - Wed, May 8
ORD
O'Hare Intl.
MCO
Orlando Intl.
$94 Roundtrip, found 3 days ago
$94
Roundtrip
found 3 days ago
Tue, Apr 30 - Tue, Apr 30
ORD
O'Hare Intl.
MCO
Orlando Intl.
$96 Roundtrip, found 3 days ago
$96
Roundtrip
found 3 days ago
Thu, May 23 - Tue, Jun 4
ORD
O'Hare Intl.
MCO
Orlando Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Mon, Apr 29 - Sat, May 4
ORD
O'Hare Intl.
MCO
Orlando Intl.
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Tue, Apr 30 - Thu, May 2
ORD
O'Hare Intl.
MCO
Orlando Intl.
$99 Roundtrip, found 3 days ago
$99
Roundtrip
found 3 days ago
Sat, Apr 27 - Sat, May 4
MDW
Midway Intl.
MCO
Orlando Intl.
$100 Roundtrip, found 5 days ago
$100
Roundtrip
found 5 days ago
Mon, Apr 29 - Wed, May 1
ORD
O'Hare Intl.
MCO
Orlando Intl.
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
Mon, Apr 29 - Wed, May 1
ORD
O'Hare Intl.
MCO
Orlando Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Sun, May 5 - Wed, May 8
ORD
O'Hare Intl.
MCO
Orlando Intl.
$104 Roundtrip, found 3 days ago
$104
Roundtrip
found 3 days ago
Mon, Apr 29 - Wed, May 1
ORD
O'Hare Intl.
MCO
Orlando Intl.
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago
Sat, May 25 - Mon, Jun 3
ORD
O'Hare Intl.
MCO
Orlando Intl.
$556 Roundtrip, found 1 day ago
$556
Roundtrip
found 1 day ago