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, Apr 23 - Tue, Apr 23
MDW
Midway Intl.
TPA
Tampa Intl.
$63 Roundtrip, found 6 days ago
$63
Roundtrip
found 6 days ago
Tue, Apr 23 - Tue, Apr 30
MDW
Midway Intl.
TPA
Tampa Intl.
$76 Roundtrip, found 6 days ago
$76
Roundtrip
found 6 days ago
Tue, Apr 23 - Fri, May 3
MDW
Midway Intl.
TPA
Tampa Intl.
$81 Roundtrip, found 6 days ago
$81
Roundtrip
found 6 days ago
Mon, Apr 29 - Mon, Apr 29
MDW
Midway Intl.
TPA
Tampa Intl.
$83 Roundtrip, found 6 days ago
$83
Roundtrip
found 6 days ago
Wed, Apr 24 - Thu, Apr 25
MDW
Midway Intl.
TPA
Tampa Intl.
$85 Roundtrip, found 6 days ago
$85
Roundtrip
found 6 days ago
Tue, Apr 23 - Sat, Apr 27
MDW
Midway Intl.
TPA
Tampa Intl.
$88 Roundtrip, found 6 days ago
$88
Roundtrip
found 6 days ago
Fri, Apr 26 - Fri, Apr 26
MDW
Midway Intl.
TPA
Tampa Intl.
$93 Roundtrip, found 6 days ago
$93
Roundtrip
found 6 days ago
Mon, Apr 29 - Tue, Apr 30
MDW
Midway Intl.
TPA
Tampa Intl.
$94 Roundtrip, found 4 days ago
$94
Roundtrip
found 4 days ago
Wed, May 8 - Fri, May 10
ORD
O'Hare Intl.
TPA
Tampa Intl.
$95 Roundtrip, found 5 days ago
$95
Roundtrip
found 5 days ago
Tue, May 7 - Sat, May 11
ORD
O'Hare Intl.
TPA
Tampa Intl.
$96 Roundtrip, found 5 days ago
$96
Roundtrip
found 5 days ago
Tue, Apr 23 - Fri, Apr 26
MDW
Midway Intl.
TPA
Tampa Intl.
$98 Roundtrip, found 6 days ago
$98
Roundtrip
found 6 days ago
Tue, May 7 - Sat, May 11
ORD
O'Hare Intl.
TPA
Tampa Intl.
$101 Roundtrip, found 5 days ago
$101
Roundtrip
found 5 days ago
Tue, Apr 23 - Thu, Apr 25
MDW
Midway Intl.
TPA
Tampa Intl.
$104 Roundtrip, found 6 days ago
$104
Roundtrip
found 6 days ago
Fri, Apr 26 - Tue, Apr 30
MDW
Midway Intl.
TPA
Tampa Intl.
$106 Roundtrip, found 6 days ago
$106
Roundtrip
found 6 days ago
Mon, Apr 29 - Tue, Apr 30
MDW
Midway Intl.
TPA
Tampa Intl.
$108 Roundtrip, found 4 days ago
$108
Roundtrip
found 4 days ago
Tue, May 7 - Sat, May 11
ORD
O'Hare Intl.
TPA
Tampa Intl.
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Tue, May 7 - Sat, May 11
ORD
O'Hare Intl.
TPA
Tampa Intl.
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Tue, Jun 25 - Sat, Jun 29
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$211 Roundtrip, found 1 day ago
$211
Roundtrip
found 1 day ago
Mon, Jun 10 - Sat, Jun 15
MDW
Midway Intl.
TPA
Tampa Intl.
$218 Roundtrip, found 19 hours ago
$218
Roundtrip
found 19 hours ago
Tue, May 7 - Sat, May 11
ORD
O'Hare Intl.
TPA
Tampa Intl.
$289 Roundtrip, found 5 days ago
$289
Roundtrip
found 5 days ago