S$121 Cheap Flights from Houston to Chicago

View S$121 flight on Fri, 22 Aug, 2025Opens in a new window

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

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Cheap Flights from Houston to Chicago (HOU-ORD)

Prices were available within the past 7 days and start at S$121 for one-way flights and S$242 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, 22 Aug - Fri, 29 Aug
IAH
Houston
ORD
Chicago
S$242 Return, found 5 days ago
S$242
Return
found 5 days ago
Select American Airlines flight, departing Fri, 22 Aug from Houston to Chicago, returning Fri, 29 Aug, priced at S$242 found 5 days ago
United
Fri, 22 Aug - Fri, 29 Aug
IAH
Houston
ORD
Chicago
S$242 Return, found 5 days ago
S$242
Return
found 5 days ago
Select United flight, departing Fri, 22 Aug from Houston to Chicago, returning Fri, 29 Aug, priced at S$242 found 5 days ago
United
Thu, 7 Aug - Thu, 14 Aug
IAH
Houston
ORD
Chicago
S$258 Return, found 3 days ago
S$258
Return
found 3 days ago
Select United flight, departing Thu, 7 Aug from Houston to Chicago, returning Thu, 14 Aug, priced at S$258 found 3 days ago
United
Thu, 7 Aug - Thu, 14 Aug
IAH
Houston
ORD
Chicago
S$259 Return, found 3 days ago
S$259
Return
found 3 days ago
Select United flight, departing Thu, 7 Aug from Houston to Chicago, returning Thu, 14 Aug, priced at S$259 found 3 days ago
Delta
Fri, 22 Aug - Fri, 29 Aug
IAH
Houston
ORD
Chicago
S$260 Return, found 5 days ago
S$260
Return
found 5 days ago
Select Delta flight, departing Fri, 22 Aug from Houston to Chicago, returning Fri, 29 Aug, priced at S$260 found 5 days ago
United
Sat, 23 Aug - Sat, 30 Aug
IAH
Houston
ORD
Chicago
S$264 Return, found 4 days ago
S$264
Return
found 4 days ago
Select United flight, departing Sat, 23 Aug from Houston to Chicago, returning Sat, 30 Aug, priced at S$264 found 4 days ago
United
Thu, 7 Aug - Thu, 14 Aug
IAH
Houston
ORD
Chicago
S$269 Return, found 3 days ago
S$269
Return
found 3 days ago
Select United flight, departing Thu, 7 Aug from Houston to Chicago, returning Thu, 14 Aug, priced at S$269 found 3 days ago
United
Fri, 22 Aug - Fri, 29 Aug
IAH
Houston
ORD
Chicago
S$276 Return, found 5 days ago
S$276
Return
found 5 days ago
Select United flight, departing Fri, 22 Aug from Houston to Chicago, returning Fri, 29 Aug, priced at S$276 found 5 days ago
Delta
Sun, 24 Aug - Sun, 31 Aug
HOU
Houston
ORD
Chicago
S$278 Return, found 3 days ago
S$278
Return
found 3 days ago
Select Delta flight, departing Sun, 24 Aug from Houston to Chicago, returning Sun, 31 Aug, priced at S$278 found 3 days ago
Delta
Sat, 8 Nov - Tue, 11 Nov
IAH
Houston
ORD
Chicago
S$278 Return, found 1 day ago
S$278
Return
found 1 day ago
Select Delta flight, departing Sat, 8 Nov from Houston to Chicago, returning Tue, 11 Nov, priced at S$278 found 1 day 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$508 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, Delta
Return price
S$242
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 American Airlines, United, Delta. 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$121 and roundtrip prices from S$242*.
 

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$242. 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

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George Bush Intercontinental to Chicago
S$241.50
*Available to Expedia members.