Cheap flights from Houston Hobby Airport to Chicago from $95

The month of February is, on average, the cheapest month to fly to Chicago from Houston Hobby Airport, with most prices found around $29. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Houston Hobby Airport to Chicago during January average around $36.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $295. 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 Hobby Airport to Chicago for around $397.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Houston Hobby Airport to Chicago during this time can be as low as $225. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $618.

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

You are more likely to see cheaper flights to Chicago from Houston Hobby Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $222 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Houston Hobby Airport for as low as $146 on momondo.

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

You could potentially save up to 51% on your flight if you consider stops on a Houston Hobby Airport to Chicago flight.

As of May 2026, prices for Houston Hobby Airport to Chicago flights are approximately 38% more expensive when compared to flights at the same time last year.

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

Frontier, Spirit Airlines and United Airlines are the top three most popular airlines that fly to Chicago from Houston Hobby Airport according to our data. Frontier is the first choice among our users, with 31% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 20% 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 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.

Saturday 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.

4 flights are operational daily from Houston Hobby Airport to Chicago as of May 2026. The most popular departure time for this route is 8:00AM, with 53% of flights per day taking off in the afternoon.

31 flights are operational weekly from Houston Hobby Airport to Chicago as of May 2026. The most popular departure day for this route is Mon, with 23% of flights per week taking off on this day.