Cheap flights from Chicago Midway Airport to Houston from $106

The month of December is, on average, the cheapest month to fly to Houston from Chicago Midway Airport, with most prices found around $271. The month of May is another great option to travel to Houston, with average flight prices from Chicago Midway Airport averaging around $287.

On average, the least expensive day to fly to Houston from Chicago Midway Airport is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $375. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Houston on Monday is $527.

Our data shows that the cheapest Chicago Midway Airport to Houston flights are usually those with departure times in the afternoon. Our users have found flights to Houston in the afternoon for as low as $351. Try not to purchase tickets in the morning because they tend to be around $423. 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 Midway - Houston flight prices

You are more likely to see cheaper flights to Houston from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Houston for around $374 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Houston from Chicago Midway Airport for as low as $216 on momondo.

There is only 1 cabin class available to choose from on Chicago Midway Airport to Houston flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Southwest, Frontier, and Delta are the most popular carriers operating from Chicago Midway to Houston

Southwest, Frontier and United Airlines are the top three most popular airlines that fly to Houston from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 76% of people opting to fly with this airline when traveling to Houston. Keep in mind that there are 3 different airlines that fly to Houston on a routine basis, so you have a few additional options to choose from.

Historically, on average around 21% 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 114 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.

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, Southwest have had the least number of delays on this route over the last 12 months; with about 20% of their flights experiencing any sort of delay.

3 flights are operational daily from Chicago Midway Airport to Houston as of November 2026. The most popular departure time for this route is 10:00AM, with 46% of flights per day taking off in the afternoon.

The number of flights available between Chicago Midway Airport and Houston is 25 per week as of November 2026. The most frequent departure day is Mon, with 24% of weekly flights leaving on this day.