Cheap flights from Chicago to Houston from $85

In general, September is the cheapest month to fly from Chicago to Houston Hobby Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $45. The month of August is another great option to travel to Houston Hobby Airport, with average flight prices from Chicago averaging around $58.

Our data shows that Wednesday is the least expensive day to fly to Houston Hobby Airport. Tickets to fly out on this day can be as low as $336. 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 Hobby Airport on Sunday is $503.

According to our data, the cheapest time of day to fly to Houston Hobby Airport is in the evening. momondo users have found flights departing from Chicago to Houston Hobby Airport in the evening for as low as $279. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $364. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Chicago Midway to Houston Hobby for the best Chicago - Houston Hobby flight prices

You are more likely to see cheaper flights to Houston Hobby Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Houston Hobby Airport for around $230 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Houston Hobby Airport from Chicago for as low as $118 on momondo.

No. A direct flight is the cheapest option for a flight between Chicago to Houston Hobby Airport.

As of May 2026, prices for Chicago to Houston Hobby Airport flights are approximately 33% more expensive when compared to flights at the same time last year.

Delta and Southwest are the most popular carriers operating from Chicago to Houston Hobby

Frontier, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Houston Hobby Airport from Chicago according to our data. Frontier is the first choice among our users, with 32% of people opting to fly with this airline when traveling to Houston Hobby Airport. Keep in mind that there are 5 different airlines that fly to Houston Hobby Airport 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 116 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 19% of their flights experiencing any sort of delay.

6 flights are operational daily from Chicago to Houston Hobby Airport as of May 2026. The most popular departure time for this route is 10:00AM, with 52% of flights per day taking off at noon.

As of May 2026, 46 flights take off from Chicago and land in Houston Hobby Airport each week. The most common flight departure day for this route is Thu, with 26% of weekly flights taking off on this day.