Flights from Houston to Winthrop Harbor

Cheapest flights from Houston

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.

Thu, Aug 28 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$104 Roundtrip, found 3 days ago

$104

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Aug 28 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $104 found 3 days ago

Thu, Aug 28 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$109 Roundtrip, found 3 days ago

$109

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Aug 28 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $109 found 3 days ago

Thu, Aug 28 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$114 Roundtrip, found 3 days ago

$114

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Aug 28 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $114 found 3 days ago

Thu, Aug 28 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$119 Roundtrip, found 3 days ago

$119

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Aug 28 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $119 found 3 days ago

Thu, Aug 21 - Sun, Aug 24

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$122 Roundtrip, found 3 days ago

$122

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Aug 21 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 24, priced at $122 found 3 days ago

Thu, Aug 21 - Sun, Aug 24

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$127 Roundtrip, found 3 days ago

$127

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Aug 21 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 24, priced at $127 found 3 days ago

Sun, Jul 27 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$130 Roundtrip, found 6 days ago

$130

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sun, Jul 27 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $130 found 6 days ago

Mon, Aug 25 - Sat, Aug 30

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$132 Roundtrip, found 3 days ago

$132

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Mon, Aug 25 from George Bush Intercontinental to O'Hare Intl., returning Sat, Aug 30, priced at $132 found 3 days ago

Thu, Aug 28 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$134 Roundtrip, found 3 days ago

$134

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Aug 28 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $134 found 3 days ago

Thu, Aug 21 - Sun, Aug 24

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$137 Roundtrip, found 3 days ago

$137

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Aug 21 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 24, priced at $137 found 3 days ago

Tue, Jul 29 - Sat, Aug 2

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$140 Roundtrip, found 6 days ago

$140

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Tue, Jul 29 from George Bush Intercontinental to O'Hare Intl., returning Sat, Aug 2, priced at $140 found 6 days ago

Thu, Aug 28 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$142 Roundtrip, found 3 days ago

$142

Roundtrip

found 3 days ago

Select United flight, departing Thu, Aug 28 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $142 found 3 days ago

Thu, Aug 28 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$142 Roundtrip, found 3 days ago

$142

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Aug 28 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $142 found 3 days ago

Sun, Jul 27 - Fri, Aug 1

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$146 Roundtrip, found 6 days ago

$146

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sun, Jul 27 from George Bush Intercontinental to O'Hare Intl., returning Fri, Aug 1, priced at $146 found 6 days ago

Thu, Aug 28 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$147 Roundtrip, found 3 days ago

$147

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Aug 28 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $147 found 3 days ago

Thu, Aug 28 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$149 Roundtrip, found 3 days ago

$149

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Aug 28 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $149 found 3 days ago

Thu, Aug 21 - Sun, Aug 24

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$177 Roundtrip, found 3 days ago

$177

Roundtrip

found 3 days ago

Select United flight, departing Thu, Aug 21 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 24, priced at $177 found 3 days ago

Thu, Aug 21 - Sun, Aug 24

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$177 Roundtrip, found 3 days ago

$177

Roundtrip

found 3 days ago

Select American Airlines flight, departing Thu, Aug 21 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 24, priced at $177 found 3 days ago

Tue, Jul 29 - Sat, Aug 2

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$217 Roundtrip, found 6 days ago

$217

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Jul 29 from George Bush Intercontinental to O'Hare Intl., returning Sat, Aug 2, priced at $217 found 6 days ago

Thu, Aug 28 - Sun, Aug 31

HOU

William P. Hobby

ORD

O'Hare Intl.

$288 Roundtrip, found 3 days ago

$288

Roundtrip

found 3 days ago

Select Delta flight, departing Thu, Aug 28 from William P. Hobby to O'Hare Intl., returning Sun, Aug 31, priced at $288 found 3 days ago