Cheap flights from Houston Hobby Airport to Chicago from $105

The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from Houston Hobby Airport, with most prices found around $210. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Houston Hobby Airport during the month December is also very affordable. Most momondo users find prices during this month for around $225.

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Houston Hobby Airport. The lowest ticket price found for a Saturday departure recently was $307. 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, Sunday is the most expensive day to depart from Houston Hobby Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $492.

Flying to Chicago Midway Airport from Houston Hobby Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $282 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $342. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago Midway Airport from Houston Hobby Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $354 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 Hobby Airport for as low as $196 on momondo.

There is only 1 cabin class available to choose from on Houston Hobby Airport 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.

You could potentially save up to 58% on your flight if you consider stops on a Houston Hobby Airport to Chicago Midway Airport flight.

As of September 2026, prices for Houston Hobby Airport to Chicago Midway Airport flights are approximately 377% more expensive when compared to flights at the same time last year.

Historically, on average around 24% 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 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.

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 24% of their flights experiencing any sort of delay.

As of September 2026, 4 flights take off from Houston Hobby Airport and land in Chicago Midway Airport each day. The most common flight departure time for this route is 7:00PM, with 37% of daily flights taking off at noon.

As of September 2026, 29 flights take off from Houston Hobby Airport and land in Chicago Midway Airport each week. The most common flight departure day for this route is Tue, with 24% of weekly flights taking off on this day.