Skip to main content
Beginning of main content

Cheap Flights from Houston to Chicago $187.59

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 (IAH 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 (IAH to MDW)

Question : Looking for the cheapest flight over the next 30 days?
Answer : As of January 16th, the cheapest day to fly from Houston to Chicago is January 27th. Tickets have been sold for 29% below the average price for this route.

Question : How long do most people stay in Chicago when they fly in from Houston?
Answer : The average time spent in Chicago by passengers flying from IAH is five days.

Question : Would you be willing to change your travel days if it saved you money?
Answer : In February, Thursday is your cheapest day to fly. Flexibility is paramount when booking travel plans in order to keep costs down.

Question : How often is the price changing when booking a trip from George Bush Intercontinental Airport (IAH) to Chicago Midway International Airport (MDW)?
Answer : Prices are fluctuating much more for this route than most routes. Remember, you can save by booking further in advance.

Question : Which airline is least likely to get you to MDW on time?
Answer : Over the past month, Executive Jet Management is late on 100% of flights from George Bush Intercontinental Airport (IAH) to Chicago Midway International Airport (MDW). If you're on Executive Jet Management, be sure to sign up for the delay notifications to stay up to date with your flight's status.

Question : What's the likelihood of you being delayed on this route?
Answer : The best way to measure a flight's promptness combines both on-time percentage and total delay minutes. IAH to MDW currently has 0.6 stars out of 5, earning the route a far below-average rating compared to the rest of the world.