S$139 Cheap Flights from Houston to Chicago

View S$139 flight on Tue, 19 Aug, 2025Opens in a new window

Popular airlines from Houston William Hobby Airport (HOU) to Chicago O'Hare Intl. Airport (ORD)

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 40% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Houston to Chicago (HOU-ORD)

Prices were available within the past 7 days and start at S$139 for one-way flights and S$277 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 26 Sep - Mon, 29 Sep
IAH
Houston
ORD
Chicago
S$277 Return, found 2 days ago
S$277
Return
found 2 days ago
Select Delta flight, departing Fri, 26 Sep from Houston to Chicago, returning Mon, 29 Sep, priced at S$277 found 2 days ago
Delta
Tue, 19 Aug - Tue, 26 Aug
IAH
Houston
ORD
Chicago
S$278 Return, found 13 hours ago
S$278
Return
found 13 hours ago
Select Delta flight, departing Tue, 19 Aug from Houston to Chicago, returning Tue, 26 Aug, priced at S$278 found 13 hours ago
Delta
Tue, 19 Aug - Tue, 26 Aug
IAH
Houston
ORD
Chicago
S$285 Return, found 13 hours ago
S$285
Return
found 13 hours ago
Select Delta flight, departing Tue, 19 Aug from Houston to Chicago, returning Tue, 26 Aug, priced at S$285 found 13 hours ago
American Airlines
Tue, 19 Aug - Tue, 26 Aug
IAH
Houston
ORD
Chicago
S$290 Return, found 13 hours ago
S$290
Return
found 13 hours ago
Select American Airlines flight, departing Tue, 19 Aug from Houston to Chicago, returning Tue, 26 Aug, priced at S$290 found 13 hours ago
United
Tue, 19 Aug - Tue, 26 Aug
IAH
Houston
ORD
Chicago
S$290 Return, found 13 hours ago
S$290
Return
found 13 hours ago
Select United flight, departing Tue, 19 Aug from Houston to Chicago, returning Tue, 26 Aug, priced at S$290 found 13 hours ago
United
Tue, 19 Aug - Tue, 26 Aug
IAH
Houston
ORD
Chicago
S$291 Return, found 13 hours ago
S$291
Return
found 13 hours ago
Select United flight, departing Tue, 19 Aug from Houston to Chicago, returning Tue, 26 Aug, priced at S$291 found 13 hours ago
Delta
Tue, 19 Aug - Tue, 26 Aug
IAH
Houston
ORD
Chicago
S$309 Return, found 13 hours ago
S$309
Return
found 13 hours ago
Select Delta flight, departing Tue, 19 Aug from Houston to Chicago, returning Tue, 26 Aug, priced at S$309 found 13 hours ago
United
Sun, 17 Aug - Thu, 21 Aug
IAH
Houston
ORD
Chicago
S$310 Return, found 4 days ago
S$310
Return
found 4 days ago
Select United flight, departing Sun, 17 Aug from Houston to Chicago, returning Thu, 21 Aug, priced at S$310 found 4 days ago
United
Fri, 26 Sep - Mon, 29 Sep
IAH
Houston
ORD
Chicago
S$315 Return, found 2 days ago
S$315
Return
found 2 days ago
Select United flight, departing Fri, 26 Sep from Houston to Chicago, returning Mon, 29 Sep, priced at S$315 found 2 days ago
American Airlines
Tue, 19 Aug - Tue, 26 Aug
IAH
Houston
ORD
Chicago
S$316 Return, found 13 hours ago
S$316
Return
found 13 hours ago
Select American Airlines flight, departing Tue, 19 Aug from Houston to Chicago, returning Tue, 26 Aug, priced at S$316 found 13 hours ago

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

January is typically the cheapest month to fly

From S$64 - S$505 per traveller.

Graph displaying average flight prices per month

Houston to Chicago route information
Origin airport
George Bush Intercontinental
Destination airport
O'Hare Intl.
Airlines serving
American Airlines
Return price
S$276
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 O'Hare Intl. 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 O'Hare Intl. 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$277*.
 

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.

Frequently asked questions

How much is a flight from HOU to ORD?
If you're planning on travelling between William P. Hobby Airport and O'Hare Airport, round-trip flights start from S$277. This figure is based on airfares advertised within the last 7 days on Expedia for flights departing within the next year, so don't wait around. Book today and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from HOU to O'Hare Airport?
Most flights can be cancelled online, but whether or not you are charged a fee varies between airlines. If you do have to cancel your escape, follow the instructions in the Customer Service Portal.
How do I find cheap flights from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for HOU to O'Hare Intl. Airport (ORD) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from HOU to O'Hare Airport?
Expect to be cruising at altitude for a while, as the flight distance between William P. Hobby Airport and O'Hare Airport is 1,500 kilometres. Create a playlist of your favourite tunes before you leave home to keep yourself entertained during your flight.
Which airlines fly direct from HOU to ORD?
Unfortunately, there are no airlines that fly direct between William P. Hobby Airport (HOU) and O'Hare Airport. You'll have to book a flight with at least one stop.
Are HOU to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from William P. Hobby Airport to O'Hare Intl. Airport (ORD) last minute could save you some serious cash. However, it could end up costing a great deal more! If you'd rather err on the side of caution, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to a year in advance. If your preferred air carrier hasn't released tickets yet, check back regularly as deals are updated all the time on Expedia.

Explore a world of travel with Expedia

Chicago Airports

Chicago

Houston Airports

Houston

George Bush Intercontinental to Chicago
S$276.20
*Available to Expedia members.