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When’s a good time to book a flight from Houston to Chicago?

What’s the cheapest day of the week to fly from Houston to Chicago?

What is the cheapest month to fly from Houston to Chicago?

‡This information is based on historical data from the last 365 days.

Finding Affordable Flights from Houston to Chicago
  • Plan Ahead - One of the keys to securing cheap flights from Houston to Chicago is to plan your trip well in advance. Airlines often offer lower prices for those who book tickets months ahead. Keep an eye on special promotions and sales events, which can yield significant savings.
  • Flexibility is Key - Being flexible with your travel dates can also lead to substantial cost savings. Consider flying during off-peak seasons or on weekdays when prices tend to be lower.
  • Set Price Alerts - To keep tabs on flight prices, consider setting up fare alerts. These alerts will notify you when fares from Houston to Chicago drop, giving you the opportunity to grab cheap deals.
  • Consider Nearby Airports - If Chicago has multiple airports, check the prices at each one. Sometimes, flying into a nearby airport and then taking a short train or bus ride to your destination can be a much cheaper option.
  • Bundle and Save - Booking your flight and accommodation together as a package can often result in significant savings. CheapOair offers these bundled deals, so make sure to explore this option.

When is the Cheapest Time to Book Flights from Houston to Chicago?

Got flexible travel dates? Use our flight data from the past year to discover ideal times to fly from Houston to Chicago. Find out which months and days typically offer lower fares and score our best savings.

CheapOair provides the predicted prices for one-way trips or round-trips with a duration of 7 days for domestic and 14 days for international trips based on historical data and available flight information. Graphs are estimates only. Prices are subject to change and can't be guaranteed until ticketed.
Estimated price for
Round-trip

‡Graphs are estimates only. Based on historical data and available flight information. Prices are subject to change and cannot be guaranteed until ticketed.

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Houston to Chicago Flight Route Information

Travel Distance:926 Miles
Airlines Flying This Route: United Airlines, Spirit Airlines, American Airlines
Weekly Flights:447
Avg. Flight Duration:2.43 Hours

Insights About Flying from Houston to Chicago

Q. Which is the high season to travel from Houston to Chicago?

A. The month of October is considered the high season for flying from HOU to CHI. Traveling during the high season can affect ticket prices and availability, making this data crucial for trip planning.

Q. How many direct flights are available from HOU to CHI?

A. There are a total of 1791 direct flights from Houston to Chicago. For travelers seeking convenience and shorter travel times, this data is important when choosing flight options.

Q. Which is the low season to travel from Houston to Chicago?

A. January is considered the low season for traveling from Houston to Chicago, Illinois. Travelers looking for cost-effective options and fewer crowds may consider traveling during this period.

Q. How many daily flights are there between Houston to Chicago?

A. There are as many as 59 daily flights available for travelers between HOU to CHI. This data offers flexibility in choosing departure times that best suit your schedule.

Q. At what time does the last flight depart to Chicago?

A. The last flight to Chicago typically departs between 9:00PM - 10:00PM. Travelers who prefer late-night departures will find this information valuable for planning their journey.

Q. What percentage of travelers spent an average of 1 days in Chicago, Illinois?

A. Approximately 36.29% of travelers spent an average of 1 days exploring Chicago. This information can assist in planning the duration of your stay in Chicago

Q. What percentage of HOU to CHI flyers traveled with kids under 14?

A. About 7% of passengers on flights from Houston to Chicago were accompanied by children under the age of 14. This information is useful if you're planning a family trip and want to know how common it is to travel with young children on this route.

Q. What percentage of Houston to Chicago travelers were over 60 years old?

A. A notable 13% of travelers were aged 60 or older. This statistic provides insights for senior travelers or those seeking a mature travel demographic.

Q. What percentage of HOU to CHI travelers were millennials?

A. Millennials make up a significant portion of travelers on this route, accounting for 36% of all passengers. If you're a millennial looking to connect with like-minded travelers, this statistic might interest you.

Q. What percentage of Houston to Chicago travelers were female?

A. Almost half of the passengers, approximately 49% were female. Knowing the gender distribution can be useful for solo female travelers or those interested in gender-related travel insights.

Q. What percent of Houston to Chicago travellers booked first or business class?

A. 8% of travelers booked first or business class on this route.

Q. At what time the earliest flight departs from Houston?

A. The earliest flight departs at 5:00AM - 6:00AM.

Q. On which days one can have the most flight options in Chicago?

A. Monday offer the most flight options in Chicago.

§ All flight facts are based on last 3 months' data except the highest and lowest booking months that are based on last 3 months' data.

Cheap Flights from Houston to Chicago

Looking for flights from Houston (HOU) to Chicago (CHI)? Find affordable air travel deals on CheapOair and save big on air tickets online. If you are a lover of historic buildings, then Chicago is your paradise. A tour of the city by boat, bus, bike or even on foot will take you through architectural delights, ranging from gothic to space age. John Hancock Center, Monadnock Building, The Rookery, Farnsworth House, Chicago Water Tower and Pumping Station and Robert Morris Center, among scores of others decorate the Chicago skyline. It also boasts of being home to 3 of the top 5 tallest buildings of the country, Sears Tower, Trump Tower, Aon Center. To reach Chicago, CHI from Houston, HOU you can choose from the top airlines, Spirit Airlines, US Airways and American Airlines for a comfortable and convenient journey. The average time taken by a flight to cover the distance of 942 miles between the two cities is about 2 hours and 30 minutes.
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