Cheap flights from Chicago to Houston from $55

The month of September is, on average, the cheapest month to fly to Houston from Chicago, with most prices found around $177. The month of January is another great option to travel to Houston, with average flight prices from Chicago averaging around $186.

On average, the least expensive day to fly to Houston from Chicago is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $314. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Houston on Sunday is $557.

Our data shows that the cheapest Chicago to Houston flights are usually those with departure times in the evening. Our users have found flights to Houston in the evening for as low as $265. Try not to purchase tickets in the morning because they tend to be around $358. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Chicago Midway to Houston George Bush Intcntl for the best Chicago - Houston flight prices

You are more likely to see cheaper flights to Houston from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Houston for around $227 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Houston from Chicago for as low as $161 on momondo.

There are 4 cabin classes available to choose from on Chicago to Houston flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Spirit Airlines, United Airlines, and Southwest are the most popular carriers operating from Chicago to Houston

Frontier, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Houston from Chicago according to our data. Frontier is the first choice among our users, with 29% of people opting to fly with this airline when traveling to Houston. Keep in mind that there are 6 different airlines that fly to Houston on a routine basis, so you have a few additional options to choose from.

Historically, on average around 19% of flights between Chicago and Houston have experienced a delay on any given week. The average delay length over the past 12 months has been 115 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 18% of their flights experiencing any sort of delay.

24 flights are operational daily from Chicago to Houston as of March 2026. The most popular departure time for this route is 8:00PM, with 40% of flights per day taking off in the afternoon.

As of March 2026, 171 flights take off from Chicago and land in Houston each week. The most common flight departure day for this route is Thu, with 38% of weekly flights taking off on this day.