Cheap flights from Chicago Midway Airport to Houston from $105

In general, September is the cheapest month to fly from Chicago Midway Airport to Houston Hobby Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $173. The month of October is another great option to travel to Houston Hobby Airport, with average flight prices from Chicago Midway Airport averaging around $254.

Our data shows that Wednesday is the least expensive day to fly to Houston Hobby Airport. Tickets to fly out on this day can be as low as $350. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Houston Hobby Airport on Sunday is $477.

According to our data, the cheapest time of day to fly to Houston Hobby Airport is in the afternoon. momondo users have found flights departing from Chicago Midway Airport to Houston Hobby Airport in the afternoon for as low as $321. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $400. 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 Hobby flight prices

You are more likely to see cheaper flights to Houston Hobby Airport from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Houston Hobby Airport for around $311 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Houston Hobby Airport from Chicago Midway Airport for as low as $214 on momondo.

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

Southwest is the most popular carrier operating from Chicago Midway to Houston Hobby

Southwest, Frontier and United Airlines are the top three most popular airlines that fly to Houston Hobby Airport from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 67% of people opting to fly with this airline when traveling to Houston Hobby Airport. Keep in mind that there are 3 different airlines that fly to Houston Hobby Airport 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 113 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights at night 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 21% of their flights experiencing any sort of delay.

1 flights are operational daily from Chicago Midway Airport to Houston Hobby Airport as of August 2026. The most popular departure time for this route is 10:00AM, with 58% of flights per day taking off at noon.

The number of flights available between Chicago Midway Airport and Houston Hobby Airport is 10 per week as of August 2026. The most frequent departure day is Wed, with 60% of weekly flights leaving on this day.