$99 Cheap Delta flights Houston (HOU) to Chicago (CHI)

View $99 flight on Mon, Jan 19, 2026Opens in a new window
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$99 Cheap Delta flights Houston (HOU) to Chicago (CHI)

Prices were available within the past 7 days and start at $99 for one-way flights and $157 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Jan 18 - Sat, Jan 24
HOU
Houston
MDW
Chicago
$157 Roundtrip, found 3 hours ago
$157
Roundtrip
found 3 hours ago
Select Delta flight, departing Sun, Jan 18 from Houston to Chicago, returning Sat, Jan 24, priced at $157 found 3 hours ago
Delta
Sun, Jan 18 - Sat, Jan 24
HOU
Houston
MDW
Chicago
$192 Roundtrip, found 3 hours ago
$192
Roundtrip
found 3 hours ago
Select Delta flight, departing Sun, Jan 18 from Houston to Chicago, returning Sat, Jan 24, priced at $192 found 3 hours ago
Delta
Tue, Jan 6 - Fri, Jan 9
HOU
Houston
ORD
Chicago
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jan 6 from Houston to Chicago, returning Fri, Jan 9, priced at $197 found 1 hour ago
Delta
Wed, Dec 17 - Wed, Dec 31
HOU
Houston
MDW
Chicago
$198 Roundtrip, found 15 hours ago
$198
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, Dec 17 from Houston to Chicago, returning Wed, Dec 31, priced at $198 found 15 hours ago
Delta
Mon, Dec 15 - Tue, Dec 16
HOU
Houston
ORD
Chicago
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Dec 15 from Houston to Chicago, returning Tue, Dec 16, priced at $228 found 1 day ago
Delta
Mon, Feb 9 - Thu, Feb 12
HOU
Houston
ORD
Chicago
$238 Roundtrip, found 10 hours ago
$238
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, Feb 9 from Houston to Chicago, returning Thu, Feb 12, priced at $238 found 10 hours ago
Delta
Tue, Jan 6 - Fri, Jan 9
HOU
Houston
ORD
Chicago
$267 Roundtrip, found 1 hour ago
$267
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jan 6 from Houston to Chicago, returning Fri, Jan 9, priced at $267 found 1 hour ago
Flights from Houston (HOU) to Chicago (MDW)
Origin airport
William P. Hobby
Destination airport
Midway Intl.
Distance
937 mi

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