144 € Cheap Flights from Chicago Midway to Houston Hobby

Compare Chicago Midway to Houston Hobby flight deals

Find the cheapest month or even day of the year to fly to Houston Hobby

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Flight deals from Chicago Midway to Houston Hobby

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Houston Hobby Airport? If you want to travel next month, return fares start from 144 €. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago Midway to Houston Hobby

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Houston Hobby flights are currently cheapest in May.

Direct flights from Chicago Midway to Houston Hobby

Chicago Midway to Houston Hobby: Alternative routes

Compare routes from Chicago Midway to Houston below. You may find an airport to fly into that's cheaper, faster, or easier than Houston Hobby.

Chicago to Houston: Flight information

The things to know before you go.
Cheapest flight found72 €
Cheapest month to flyJune
Average flight time2 hrs, 35 mins
Most popular airlineSouthwest Airlines
Average flights per week24

Finding cheap flights from Chicago Midway to Houston Hobby: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Houston Hobby is 144 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 35 minutes is the average flight time from Chicago Midway to Houston Hobby.
Southwest Airlines flies direct from Chicago Midway to Houston Hobby.
As of April 2026, there are 24 flights per week flying from Chicago Midway to Houston Hobby.
The cheapest month to fly from Chicago Midway to Houston Hobby is usually May.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Houston Hobby Airport on Wednesday, 6 May 2026.
Yes – the average flight time is 2 hours and 35 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Houston Hobby but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Houston is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Houston Hobby.

Flying from Chicago Midway International Airport (MDW) to William P. Hobby Airport (HOU): what you need to know

  • Around 2 hours 40 minutes is how long you'll be travelling on a direct flight from Chicago Midway International Airport to William P. Hobby Airport.

  • Chicago and Houston share the UTC-5 timezone. This means you won't need to account for any time differences.

  • Each week, there are 25 Chicago Midway International Airport to William P. Hobby Airport flights. If you want to take off as soon as possible, go for the 05:00 Southwest Airlines flight. If you're eager to make the most of your time before you fly, the last departure is at 22:55 with Southwest Airlines.

  • Your MDW to HOU flight won't wait if you're running late, so don't forget to check in on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.

  • Be prepared for longer queues in popular months like July. Arriving up to four hours ahead of international flights and two hours for domestic departures will help ensure a smooth travel experience.

  • Southwest Airlines has direct flights from Chicago Midway International Airport to William P. Hobby Airport. Book with this popular airline, then get ready to see the sights in Houston — and maybe even more of United States if you have time.

  • Southwest Airlines is the most frequently booked airline on this route.

  • The most punctual carrier offering MDW to HOU flights is Southwest Airlines. Its services land as planned 79.57% of the time.

  • Consider adding a stopover when booking your ticket from Chicago Midway International Airport to William P. Hobby Airport. Simply deselect 'Direct flights only' to break up your journey, or perhaps explore a new destination along the way. Here are some options between MDW and HOU:

    • Nashville International Airport

    • Dallas Love Field Airport

    • Austin-Bergstrom International Airport

How to find the cheapest flights from Chicago Midway International Airport (MDW) to William P. Hobby Airport (HOU)

  • 72 € is the lowest price for a one-way Chicago Midway International Airport to William P. Hobby Airport flight. A return flight starts from 144 €. These prices can change based on demand.

  • To get cheap tickets from MDW to HOU, book your journey six months ahead of your departure date.

  • Plan your trip for May. That's the cheapest month for flights from Chicago Midway International Airport to William P. Hobby Airport. If you have flexibility with your dates, try out the 'Whole month' tool to see the lowest airfare across each month.

  • Stay on top of deals for cheap flights from MDW to HOU by creating a Price Alert. We'll send you an email or notification on the app when a new low fare is offered.

  • Choose your ideal arrival and departure times, number of stops and airlines with the filters. Alternatively, sort your results by 'Cheapest' to get the best deals on flights from Chicago Midway International Airport to William P. Hobby Airport.

Handy information about Chicago Midway International Airport (MDW)

  • You'll find MDW at 5700 South Cicero.

  • 77.88% of flights that take off from Chicago Midway International Airport land at their destination on schedule.

  • Central Chicago to Chicago Midway International Airport is approximately 19 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're ride-sharing, catching a cab or driving.

  • The trip when using public transport takes roughly 45 minutes.

  • Looking for a handy hotel close to MDW? If you've booked an early flight from Chicago Midway International Airport to William P. Hobby Airport, these accommodation options will have you moments from your departure lounge:

Arriving at William P. Hobby Airport (HOU)

Getting from William P. Hobby Airport (HOU) to central Houston

  • The address for HOU is 7800 Airport Boulevard.

  • William P. Hobby Airport to central Houston has a drive time of around 20 minutes. It's approximately 19 kilometres away.

  • Travelling by public transport will take you roughly 1 hour 40 minutes.

When to fly to William P. Hobby Airport (HOU)

  • It's time to pick your dates for your flight from Chicago Midway International Airport to William P. Hobby Airport. July is the busiest month to head to Houston. If you're after a more low-key vibe, go in April.

  • The warmest month in Houston is August, with temperatures ranging between 24ºC (75ºF) and 40ºC (104ºF). Book your flights from Chicago Midway International Airport to William P. Hobby Airport in this month if this is the kind of weather you like.

  • Search for cheap tickets from MDW to HOU in January if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between 5ºC (41ºF) and 19ºC (66ºF) on average.

Explore more of United States

  • San Antonio is just one of the many places in United States waiting to be explored once you've taken in the sights of Houston. Around 306 kilometres away to the west, well-known attractions include The San Antonio River Walk, San Antonio Missions National Historical Park and San Fernando Cathedral.

  • If there's time to check out another corner of United States, consider Dallas, about 370 kilometres north of Houston. Dallas Arboretum and Botanical Gardens, Perot Museum of Nature and Science and Dallas Museum of Art are the start of reasons to visit.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.