S$139 Cheap Flights from Houston to Chicago

View S$139 flight on Tue, 5 Aug, 2025Opens in a new window

Popular airlines from Houston William Hobby Airport (HOU) to Chicago

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Cheap Flights from Houston to Chicago (HOU-CHI)

Prices were available within the past 7 days and start at S$139 for one-way flights and S$317 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 25 Oct - Mon, 27 Oct
IAH
Houston
ORD
Chicago
S$317 Return, found 3 days ago
S$317
Return
found 3 days ago
Select Delta flight, departing Sat, 25 Oct from Houston to Chicago, returning Mon, 27 Oct, priced at S$317 found 3 days ago
American Airlines
Sat, 25 Oct - Mon, 27 Oct
IAH
Houston
ORD
Chicago
S$317 Return, found 3 days ago
S$317
Return
found 3 days ago
Select American Airlines flight, departing Sat, 25 Oct from Houston to Chicago, returning Mon, 27 Oct, priced at S$317 found 3 days ago
United
Sat, 25 Oct - Mon, 27 Oct
IAH
Houston
ORD
Chicago
S$317 Return, found 3 days ago
S$317
Return
found 3 days ago
Select United flight, departing Sat, 25 Oct from Houston to Chicago, returning Mon, 27 Oct, priced at S$317 found 3 days ago
Delta
Fri, 22 Aug - Fri, 29 Aug
IAH
Houston
ORD
Chicago
S$318 Return, found 1 day ago
S$318
Return
found 1 day ago
Select Delta flight, departing Fri, 22 Aug from Houston to Chicago, returning Fri, 29 Aug, priced at S$318 found 1 day ago
Delta
Sat, 25 Oct - Mon, 27 Oct
IAH
Houston
ORD
Chicago
S$331 Return, found 3 days ago
S$331
Return
found 3 days ago
Select Delta flight, departing Sat, 25 Oct from Houston to Chicago, returning Mon, 27 Oct, priced at S$331 found 3 days ago
American Airlines
Sat, 25 Oct - Mon, 27 Oct
IAH
Houston
ORD
Chicago
S$331 Return, found 3 days ago
S$331
Return
found 3 days ago
Select American Airlines flight, departing Sat, 25 Oct from Houston to Chicago, returning Mon, 27 Oct, priced at S$331 found 3 days ago
Delta
Fri, 22 Aug - Fri, 29 Aug
IAH
Houston
ORD
Chicago
S$333 Return, found 1 day ago
S$333
Return
found 1 day ago
Select Delta flight, departing Fri, 22 Aug from Houston to Chicago, returning Fri, 29 Aug, priced at S$333 found 1 day ago
American Airlines
Fri, 22 Aug - Fri, 29 Aug
IAH
Houston
ORD
Chicago
S$343 Return, found 1 day ago
S$343
Return
found 1 day ago
Select American Airlines flight, departing Fri, 22 Aug from Houston to Chicago, returning Fri, 29 Aug, priced at S$343 found 1 day ago
United
Fri, 22 Aug - Fri, 29 Aug
IAH
Houston
ORD
Chicago
S$344 Return, found 1 day ago
S$344
Return
found 1 day ago
Select United flight, departing Fri, 22 Aug from Houston to Chicago, returning Fri, 29 Aug, priced at S$344 found 1 day ago
Delta
Fri, 22 Aug - Fri, 29 Aug
IAH
Houston
ORD
Chicago
S$352 Return, found 1 day ago
S$352
Return
found 1 day ago
Select Delta flight, departing Fri, 22 Aug from Houston to Chicago, returning Fri, 29 Aug, priced at S$352 found 1 day ago

Find the cheapest month to fly from Houston (HOU) to Chicago (CHI)

April is typically the cheapest month to fly

From S$62 - S$208 per traveller.

Graph displaying average flight prices per month

Houston to Chicago route information
Origin airport
George Bush Intercontinental
Destination airport
O'Hare Intl.
Return price
S$316
Distance
1481 km

Perfect flights from Houston to Chicago

Your Journey from Houston to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Houston to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, American Airlines, United. Our selection of flights from William P. Hobby to CHI-All Airports caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Houston to Chicago Flights

Experience the joy of finding cheap flights from William P. Hobby to CHI-All Airports that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$139 and roundtrip prices from S$317*.
 

Pre-Flight Essentials

Ensure a smooth journey from Houston to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Houston to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Houston to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Houston to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Houston to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Explore a world of travel with Expedia

Chicago Airports

Chicago

Houston to O'Hare Intl.
S$316.40
Houston Airports

Houston

George Bush Intercontinental to Chicago
S$316.40
*Available to Expedia members.