Flights from Houston to Historic Route 66

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.

Sun, Jul 27 - Thu, Aug 28

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$112 Roundtrip, found 2 days ago

$112

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sun, Jul 27 from George Bush Intercontinental to O'Hare Intl., returning Thu, Aug 28, priced at $112 found 2 days ago

Wed, Jul 9 - Sat, Jul 19

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$124 Roundtrip, found 5 days ago

$124

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Jul 9 from George Bush Intercontinental to O'Hare Intl., returning Sat, Jul 19, priced at $124 found 5 days ago

Sun, Jul 27 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$131 Roundtrip, found 2 days ago

$131

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sun, Jul 27 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $131 found 2 days ago

Fri, Jul 11 - Mon, Jul 14

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$140 Roundtrip, found 1 day ago

$140

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Jul 11 from George Bush Intercontinental to O'Hare Intl., returning Mon, Jul 14, priced at $140 found 1 day ago

Fri, Aug 29 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$147 Roundtrip, found 3 days ago

$147

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Fri, Aug 29 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $147 found 3 days ago

Sat, Jul 26 - Sun, Aug 31

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$150 Roundtrip, found 2 days ago

$150

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jul 26 from George Bush Intercontinental to O'Hare Intl., returning Sun, Aug 31, priced at $150 found 2 days ago

Fri, Aug 29 - Mon, Sep 1

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$154 Roundtrip, found 3 days ago

$154

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Fri, Aug 29 from George Bush Intercontinental to O'Hare Intl., returning Mon, Sep 1, priced at $154 found 3 days ago

Wed, Jul 30 - Thu, Aug 28

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$155 Roundtrip, found 2 days ago

$155

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jul 30 from George Bush Intercontinental to O'Hare Intl., returning Thu, Aug 28, priced at $155 found 2 days ago

Tue, Jul 8 - Wed, Jul 23

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$158 Roundtrip, found 1 day ago

$158

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Jul 8 from George Bush Intercontinental to O'Hare Intl., returning Wed, Jul 23, priced at $158 found 1 day ago

Tue, Jul 8 - Wed, Jul 23

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$159 Roundtrip, found 1 day ago

$159

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jul 8 from George Bush Intercontinental to O'Hare Intl., returning Wed, Jul 23, priced at $159 found 1 day ago

Sat, Aug 30 - Mon, Sep 1

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$177 Roundtrip, found 3 days ago

$177

Roundtrip

found 3 days ago

Select United flight, departing Sat, Aug 30 from George Bush Intercontinental to O'Hare Intl., returning Mon, Sep 1, priced at $177 found 3 days ago

Tue, Jul 8 - Wed, Jul 23

IAH

George Bush Intercontinental

ORD

O'Hare Intl.

$195 Roundtrip, found 1 day ago

$195

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Jul 8 from George Bush Intercontinental to O'Hare Intl., returning Wed, Jul 23, priced at $195 found 1 day ago

Fri, Jun 27 - Fri, Jul 4

IAH

George Bush Intercontinental

MDW

Midway Intl.

$202 Roundtrip, found 6 days ago

$202

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Fri, Jun 27 from George Bush Intercontinental to Midway Intl., returning Fri, Jul 4, priced at $202 found 6 days ago

Wed, Jun 25 - Tue, Jul 8

IAH

George Bush Intercontinental

MDW

Midway Intl.

$225 Roundtrip, found 6 days ago

$225

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Jun 25 from George Bush Intercontinental to Midway Intl., returning Tue, Jul 8, priced at $225 found 6 days ago

Tue, Jun 17 - Tue, Jun 24

IAH

George Bush Intercontinental

SGF

Springfield-Branson National

$274 Roundtrip, found 4 days ago

$274

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Jun 17 from George Bush Intercontinental to Springfield-Branson National, returning Tue, Jun 24, priced at $274 found 4 days ago

Tue, Jul 15 - Tue, Jul 22

IAH

George Bush Intercontinental

ABQ

Albuquerque Intl. Sunport

$277 Roundtrip, found 3 days ago

$277

Roundtrip

found 3 days ago

Select United flight, departing Tue, Jul 15 from George Bush Intercontinental to Albuquerque Intl. Sunport, returning Tue, Jul 22, priced at $277 found 3 days ago

Sun, Jun 15 - Mon, Jun 16

IAH

George Bush Intercontinental

OKC

Will Rogers World

$384 Roundtrip, found 1 day ago

$384

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sun, Jun 15 from George Bush Intercontinental to Will Rogers World, returning Mon, Jun 16, priced at $384 found 1 day ago

Fri, Jul 11 - Mon, Jul 14

HOU

William P. Hobby

ORD

O'Hare Intl.

$405 Roundtrip, found 1 day ago

$405

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Jul 11 from William P. Hobby to O'Hare Intl., returning Mon, Jul 14, priced at $405 found 1 day ago

Tue, Jul 22 - Fri, Jul 25

HOU

William P. Hobby

SGF

Springfield-Branson National

$467 Roundtrip, found 3 days ago

$467

Roundtrip

found 3 days ago

Select American Airlines flight, departing Tue, Jul 22 from William P. Hobby to Springfield-Branson National, returning Fri, Jul 25, priced at $467 found 3 days ago

Fri, Jun 27 - Sun, Jun 29

HOU

William P. Hobby

MDW

Midway Intl.

$674 Roundtrip, found 2 days ago

$674

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Jun 27 from William P. Hobby to Midway Intl., returning Sun, Jun 29, priced at $674 found 2 days ago