Cheap flights from Houston to Chicago from $65

The month of September is, on average, the cheapest month to fly to Chicago from Houston, with most prices found around $182. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Houston to Chicago during October average around $219.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $287. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Houston to Chicago for around $393.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Houston to Chicago during this time can be as low as $221. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $612.

Fly from Houston George Bush Intcntl to Chicago O'Hare Intl for the best Houston - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Houston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $220 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Houston for as low as $146 on momondo.

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

United Airlines, Frontier and Spirit Airlines are the top three most popular airlines that fly to Chicago from Houston according to our data. United Airlines is the first choice among our users, with 30% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 15% of flights between Houston and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 145 minutes.

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

Wednesday 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, United Airlines have had the least number of delays on this route over the last 12 months; with about 10% of their flights experiencing any sort of delay.

As of May 2026, 73 flights take off from Houston and land in Chicago each day. The most common flight departure time for this route is 6:00PM, with 42% of daily flights taking off at noon.

As of May 2026, 511 flights take off from Houston and land in Chicago each week. The most common flight departure day for this route is Fri, with 16% of weekly flights taking off on this day.