Cheap flights from Houston to Chicago from R1 896

The month of January is, on average, the cheapest month to fly to Chicago from Houston, with most prices found around R3 494. If you are unable to visit Chicago during the month of January, then departing from Houston during the month February is also very affordable. Most momondo users find prices during this month for around R3 643.

Fly from Houston Hobby to Chicago Midway 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 R4 382 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Houston for as low as R3 692 on momondo.

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

Historically, on average around 16% 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 136 minutes.

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

Tuesday is statistically the day of the week that experiences the fewest 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 fewest delays on this route over the last 12 months, with about 7% of their flights experiencing any sort of delay.

As of November 2026, 62 flights take off from Houston and land in Chicago each day. The most common flight departure time for this route is 17:00, with 45% of daily flights taking off in the afternoon.

The number of flights available between Houston and Chicago is 435 per week as of November 2026. The most frequent departure day is Fri, with 17% of weekly flights leaving on this day.