Question 1

What day of the week experiences the fewest flight delays on this route?

Accepted Answer

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

Question 2

What is the cheapest airline that flies from Houston to Chicago Midway?

Accepted Answer

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

Question 3

How many flights depart from Houston to Chicago Midway Airport on average per week?

Accepted Answer

The number of flights available between Houston and Chicago Midway Airport is 34 per week as of December 2025. The most frequent departure day is Mon, with 26% of weekly flights leaving on this day.

Question 4

How far in advance should I book a flight to Chicago Midway Airport?

Accepted Answer

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 $247 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 $129 on momondo.

Question 5

What is the cheapest day to depart on your flight to Chicago Midway Airport?

Accepted Answer

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Houston. The lowest ticket price found for a Wednesday departure recently was $269. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $387.

Question 6

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Accepted Answer

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 $206 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $245. Of course, these prices can vary depending on the time of year and what airport you fly to.

Question 7

What cabin class options are available on Houston to Chicago Midway flights?

Accepted Answer

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

Question 8

What airlines fly to Chicago Midway Airport?

Accepted Answer

Frontier, Southwest and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Houston according to our data. Frontier is the first choice among our users, with 55% 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.

Question 9

What is the cheapest month to fly to Chicago Midway Airport?

Accepted Answer

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Houston, with most prices found around $182. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Houston during the month October is also very affordable. Most momondo users find prices during this month for around $202.

Question 10

How often are flights from Houston to Chicago delayed?

Accepted Answer

Historically, on average around 17% 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 126 minutes.

Question 11

How many flights depart from Houston to Chicago Midway Airport on average per day?

Accepted Answer

As of December 2025, there are 4 flights per day flying from Houston to Chicago Midway Airport. The most common time of day flights depart is 6:00PM, with 36% of flights taking off at noon.

Question 12

Which airline has the best punctuality record on Houston to Chicago flights?

Accepted Answer

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.

Question 13

What is the cheapest Houston to Chicago Midway flight route?

Accepted Answer

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

Question 14

What is the most punctual flight time for Houston to Chicago flights?

Accepted Answer

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.

Question 15

When did momondo last update prices for flights from Houston to Chicago Midway Airport?

Accepted Answer

Prices for flights from Houston to Chicago Midway Airport were last updated today.

Question 16

How many operators does momondo search for flights from Houston to Chicago Midway Airport?

Accepted Answer

As of December 2025, there are 3 operators available to choose from for flights from Houston to Chicago Midway Airport.

Question 17

How old do you have to be to fly from Houston to Chicago Midway Airport?

Accepted Answer

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Houston to Chicago Midway Airport.

Question 18

What documentation or ID do you need to fly to Chicago Midway Airport?

Accepted Answer

The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Fastest flight time	2h 20m
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Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $88	Free Cancellation	Rating 5.8 3,075 reviews	Search Frontier flights
Southwest	PriceFrom $167	Free Cancellation	Rating 8.0 4,253 reviews	Search Southwest flights
Delta	PriceFrom $216	Free Cancellation	Rating 7.9 8,014 reviews	Search Delta flights

Cheap flights from Houston to Chicago from $52

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Houston to Chicago departing on 3/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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How to get the cheapest flight ticket from Houston to Chicago Midway Airport

What is the cheapest month to fly to Chicago Midway Airport?

What is the cheapest day to depart on your flight to Chicago Midway Airport?

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

What is the cheapest Houston to Chicago Midway flight route?

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

How far in advance should I book a flight to Chicago Midway Airport?

What cabin class options are available on Houston to Chicago Midway flights?

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

What is the cheapest airline that flies from Houston to Chicago Midway?

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

What airlines fly to Chicago Midway Airport?

How often are flights from Houston to Chicago delayed?

Historically, on average around 17% 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 126 minutes.

What is the most punctual flight time for Houston to Chicago flights?

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.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Houston to Chicago flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.

How many flights depart from Houston to Chicago Midway Airport on average per day?

As of December 2025, there are 4 flights per day flying from Houston to Chicago Midway Airport. The most common time of day flights depart is 6:00PM, with 36% of flights taking off at noon.

How many flights depart from Houston to Chicago Midway Airport on average per week?

The number of flights available between Houston and Chicago Midway Airport is 34 per week as of December 2025. The most frequent departure day is Mon, with 26% of weekly flights leaving on this day.

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How far is Houston to Chicago Midway by plane?

When did momondo last update prices for flights from Houston to Chicago Midway Airport?

How many operators does momondo search for flights from Houston to Chicago Midway Airport?

How old do you have to be to fly from Houston to Chicago Midway Airport?

What documentation or ID do you need to fly to Chicago Midway Airport?

Best airlines flying from Houston to Chicago Midway Airport

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