Cheap flights from Houston to Chicago from $103

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Houston, with most prices found around $56. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Houston during the month March is also very affordable. Most momondo users find prices during this month for around $66.

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Houston. The lowest ticket price found for a Saturday departure recently was $308. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Houston because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $425.

Flying to Chicago Midway Airport from Houston in the evening is the least expensive time of day to depart. momondo users have found prices as low as $231 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $300. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago Midway Airport from Houston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $324 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Houston for as low as $218 on momondo.

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

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

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Houston according to our data. Southwest is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 21% 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 119 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.

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 20% of their flights experiencing any sort of delay.

As of June 2026, there are 4 flights per day flying from Houston to Chicago Midway Airport. The most common time of day flights depart is 8:00AM, with 42% of flights taking off in the afternoon.

The number of flights available between Houston and Chicago Midway Airport is 32 per week as of June 2026. The most frequent departure day is Mon, with 28% of weekly flights leaving on this day.