Skip to main content
Beginning of main content

Cheap Flights from Houston to Chicago $174.05

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheapest Flights from Houston to Chicago (HOU to MDW)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Houston to Chicago (HOU to MDW)

Question : If speed is all that matters, how can you get from HOU to MDW as quickly as possible?
Answer : Southwest Airlines currently holds the fastest travel time with two hours and 20 minutes. For example, you would arrive in Chicago at 11:50 PM CDT if you left Houston at 9:30 PM CDT.

Question : In the next four weeks, what day should you book your trip?
Answer : Apr 20th has seen bookings (as of Mar 20th) as cheap as $175. That comes in 45% below the average price for this route. Saving now means you'll have more cash in your hand for the trip.

Question : Do prices fluctuate more for this route than others?
Answer : Ranging from $170 to $642, prices for HOU to MDW do fluctuate more than the majority of routes in the United States. Remember, the sooner you book, the better price you tend to get.

Question : Who's offering the cheapest round-trip flight to Chicago Midway International Airport (MDW) over the coming months?
Answer : Delta Air Lines is your best bet for finding that coveted low fare. They're offering fares as low as $170, while prices for other flights are as high as $642.

Question : Which airline has been on schedule from William P. Hobby Airport (HOU) to Chicago Midway International Airport (MDW) the most?
Answer : The current leader is Southwest Airlines with an 80% on-time rate. Spend as little time in an airport as necessary by flying with Southwest Airlines. Note that if they do have a delay, it usually lasts less than half an hour.

Question : How many days should you spend in Chicago?
Answer : The average time spent in Chicago by passengers from Houston is about one week.

Question : Can you cut down on flight costs by changing the day of the week you travel to Chicago?
Answer : The best day to fly on a budget this month is Tuesday. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.

Question : Who struggles with getting their passengers to Chicago Midway International Airport (MDW) on time?
Answer : If you decide to book your flight with Flight Options, keep an eye on your departure time. 100% of flights from William P. Hobby Airport (HOU) to Chicago Midway International Airport (MDW) are late.

Question : What is the likelihood your flight will be delayed for this route?
Answer : The Houston to Chicago route has a 79% on-time rate, ranking in the top half of the world in getting their passengers to their destinations on schedule. If a flight is late, though, expect an average of less than half an hour added to your flight time.

Question : In terms of overall promptness, how does HOU to MDW rank compared to the rest of the world?
Answer : Using the combined on-time percentage and average delay breakdown, Houston to Chicago currently has a 3 out of a possible 5 star rating. A 3-star rating means you should feel slightly worried about getting to Chicago on time.

Question : If you’re booking HOU to MDW, how many different choices of departure times do you have?
Answer : Depending on the day of the week, the number of flight times will change, but on average there are six. That is higher than the national average of five.

Question : From Houston to Chicago, which day of the week is going to have the most flight times?
Answer : When you’re flying from HOU to MDW, the day with the most flight times is Sunday, with six different options. Saturday currently offers the fewest number of flight times with five options.

Question : When traveling to Chicago from Houston, how long will you be in the air?
Answer : When flying from HOU to MDW, it will take two hours and 26 minutes on average.