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.
Tue, May 21 - Tue, May 21
MDW
Midway Intl.
IAH
George Bush Intercontinental
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Sat, May 4 - Tue, May 7
MDW
Midway Intl.
IAH
George Bush Intercontinental
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Tue, Apr 30 - Sat, May 4
MDW
Midway Intl.
IAH
George Bush Intercontinental
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Tue, Apr 23 - Tue, Apr 30
MDW
Midway Intl.
IAH
George Bush Intercontinental
$76 Roundtrip, found 4 days ago
$76
Roundtrip
found 4 days ago
Wed, May 22 - Wed, May 22
ORD
O'Hare Intl.
IAH
George Bush Intercontinental
$78 Roundtrip, found 4 hours ago
$78
Roundtrip
found 4 hours ago
Tue, May 21 - Tue, May 21
MDW
Midway Intl.
IAH
George Bush Intercontinental
$83 Roundtrip, found 1 day ago
$83
Roundtrip
found 1 day ago
Wed, May 22 - Sat, May 25
ORD
O'Hare Intl.
IAH
George Bush Intercontinental
$83 Roundtrip, just found
$83
Roundtrip
just found
Thu, May 2 - Sat, May 4
MDW
Midway Intl.
IAH
George Bush Intercontinental
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
Sat, May 4 - Sat, May 4
MDW
Midway Intl.
IAH
George Bush Intercontinental
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day ago
Sat, May 18 - Mon, May 20
ORD
O'Hare Intl.
IAH
George Bush Intercontinental
$92 Roundtrip, found 3 days ago
$92
Roundtrip
found 3 days ago
Tue, Apr 30 - Mon, May 6
MDW
Midway Intl.
IAH
George Bush Intercontinental
$93 Roundtrip, found 1 day ago
$93
Roundtrip
found 1 day ago
Wed, May 1 - Sat, May 4
ORD
O'Hare Intl.
IAH
George Bush Intercontinental
$96 Roundtrip, found 1 day ago
$96
Roundtrip
found 1 day ago
Sun, May 5 - Tue, May 7
MDW
Midway Intl.
IAH
George Bush Intercontinental
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Wed, May 22 - Wed, May 22
ORD
O'Hare Intl.
IAH
George Bush Intercontinental
$99 Roundtrip, found 4 hours ago
$99
Roundtrip
found 4 hours ago
Tue, Apr 30 - Thu, May 2
ORD
O'Hare Intl.
IAH
George Bush Intercontinental
$102 Roundtrip, found 3 days ago
$102
Roundtrip
found 3 days ago
Wed, May 22 - Wed, May 29
ORD
O'Hare Intl.
IAH
George Bush Intercontinental
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Wed, May 29 - Sat, Jun 1
ORD
O'Hare Intl.
IAH
George Bush Intercontinental
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Sat, May 4 - Sat, May 4
ORD
O'Hare Intl.
IAH
George Bush Intercontinental
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Thu, Aug 29 - Mon, Sep 2
ORD
O'Hare Intl.
HOU
William P. Hobby
$393 Roundtrip, found 4 days ago
$393
Roundtrip
found 4 days ago
Thu, Jan 30 - Mon, Feb 3
MDW
Midway Intl.
HOU
William P. Hobby
$401 Roundtrip, found 2 days ago
$401
Roundtrip
found 2 days ago