Compare Cheap Flights from Houston to Chicago
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Round Trip Flights from Houston to Chicago
Last updated on Wednesday 04/29/2026 at 05:00 AM, the fares mentioned above are for flight tickets and inclusive of fuel surcharges, service fee and taxes. Based on historical data, these fares are subject to change without prior notice and cannot be guaranteed at the time of booking. Kindly go through our terms and conditions before booking.
Book Houston To Chicago Flights
Located on Lake Michigan, Chicago is one of the culturally rich cities in Illinois. It is the third-largest city in the USA that houses diversity. The city has given us jazz, hip-hop, house music, and so much more when it comes to art. It boasts of many impressive architectural marvels, which gave it the title of birthplace of modern architecture. The skyline of Chicago is worth mentioning as it features structures like the Willis Tower and the historic Chicago Water Tower. Garfield Park Fieldhouse, Dearborn Station, McCormick Tribune Center and Citicorp Center are a few popular architectural landmarks to visit.
A vacation in Chicago is incomplete without its food. From the famous Chicago deep-dish pizza to Chicago Hot Dog and the original rainbow cone, the city offers the most tempting culinary experience to all. To plan a perfect vacation, add places like the Navy Pier, Lincoln Park Zoo, Chicago Theatre District, and Art Institute of Chicago, and witness the best of Chicago City.
Chicago is a popular vacation destination, and flights from Houston to Chicago are generally expensive. To travel under budget, you can consider booking flights for shoulder season, i.e., June and October. This is the time when you can book cheap flights from Houston to Chicago.
O'Hare International Airport and Midway International are the main airports in Chicago connected by many airlines, such as Spirit, United, Southwest, and American Airlines from Houston. You can board HOU to CHI flights from George Bush Intercontinental Airport or William P. Hobby Airport.
To get cheaper Chicago flights from Houston, call our executives. Our team is available 24/7 to assist you with cheap flight bookings.
Finding Cheap Flights From Houston To Chicago : Frequently Asked Questions
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How much are round-trip flights from Houston to Chicago?
Average cost of a round-trip flight from Houston to Chicago is around $325.
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Which upcoming date is cheapest to fly from Houston to Chicago?
In the next 90 days, flights from Houston to Chicago on will be the cheapest on May 06, 2026, June 05, 2026, and July 26, 2026.
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What?s the cheapest day of the week to fly from Houston to Chicago?
On an average, flights from Houston to Chicago tend to be cheapest on Wednesday.
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Which airlines offers the cheapest fares from Houston to Chicago?
At the moment, FRONTIER AIRLINES and SPIRIT AIRLINES offer the cheapest flights from Houston to Chicago.
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When is the peak season for traveling from Houston to Chicago?
May to July is the peak season to travel from Houston to Chicago.
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When does the first flight depart from Houston to Chicago?
The first flight from Houston to Chicago departs at 05:09 AM.
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When does the last flight from Houston to Chicago depart?
The last flight from Houston to Chicago departs at 10:04 PM.
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Cheapest Months to fly to Chicago
The cheapest months to visit Chicago are from May through July.
* The mentioned flight facts are based on the last 3 months' data. Information regarding the highest and lowest booking months is based on the last 12 months' data.
Major Carriers Operating Flights From Houston To Chicago
AMERICAN AIRLINES
$139
$291
SPIRIT AIRLINES
$87
$200
UNITED AIRLINES
$139
$284
Low Cost Carriers Operating Flights From Houston To Chicago
FRONTIER AIRLINES
$77
$209
SPIRIT AIRLINES
$87
$200
UNITED AIRLINES
$139
$284
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