Cheap Flights from Houston Hobby to Chicago Midway

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Compare Houston Hobby to Chicago Midway flight deals

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Flight deals from Houston Hobby to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Houston Hobby to Chicago Midway? Find the lowest prices on one-way and return tickets right here.

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

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

Direct flights from Houston Hobby to Chicago Midway

Houston Hobby to Chicago Midway: Alternative routes

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

Houston to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs20,142
Cheapest month to flyAugust
Average flight time2 hrs, 26 mins
Most popular airlineSouthwest Airlines
Average flights per week31

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

The best price we found for a return flight from Houston Hobby to Chicago Midway is Rs40,359. 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 26 minutes is the average flight time from Houston Hobby to Chicago Midway.
Southwest Airlines flies direct from Houston Hobby to Chicago Midway.
As of June 2025, there are 31 flights per week flying from Houston Hobby to Chicago Midway.
The cheapest month to fly from Houston Hobby to Chicago Midway is usually June 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Houston Hobby Airport to Chicago Midway Airport on Wednesday, 6 August 2025.
Yes – the average flight time is 2 hours and 26 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 Chicago Midway 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 Chicago 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 Chicago Midway.

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

  • Around 2 hours 25 minutes is how long you'll be travelling on a direct flight from William P. Hobby Airport to Chicago Midway International Airport.

  • Houston and Chicago are in the same timezone, UTC-5.

  • Every week, there are 25 William P. Hobby Airport to Chicago Midway International Airport flights. To get going as early as possible, opt for the 05:00 Southwest Airlines flight. If you're eager to make the most of your time before flying, the last departure is at 22:40 with Southwest Airlines.

  • For a smooth journey, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This way, you'll have plenty of time to catch your HOU to MDW flight.

  • Travelling during a peak month such as July? Major public holidays and other high seasons can lead to longer lines and delays at airport checkpoints. Be extra cautious and get there up to four hours ahead of international flights and two hours before a domestic departure.

  • Southwest Airlines is your gateway to discovering Chicago (and maybe even some other great parts of United States!). Browse the direct flights from William P. Hobby Airport to Chicago Midway International Airport offered by this popular carrier.

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

  • With 78.62% of services landing on schedule, Southwest Airlines is the most punctual carrier offering HOU to MDW flights.

  • We make it a piece of cake to book a flight with a stopover. To see your options for tickets from William P. Hobby Airport to Chicago Midway International Airport, uncheck 'Direct flights only.' Then, pick a flight that has a stop long enough to explore your chosen city. Some great stopovers between HOU and MDW include:

    • Dallas Love Field Airport

    • Louisville International Airport-Standiford Field

    • Kansas City International Airport

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

  • Currently, Rs20,142 is the lowest price we've seen for a one-way William P. Hobby Airport to Chicago Midway International Airport flight. The best price for a return ticket is Rs40,359. Remember that fares can change due to availability at the time of booking.

  • To get cheap tickets from HOU to MDW, reserve your journey six months before your departure date.

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

  • There's no need to check every day to find out if fares have dropped when you create a Price Alert. We'll update you the moment the price changes on cheap flights from HOU to MDW.

  • Tailor your flights with filters. Pick your arrival and departure times, total journey duration and airlines. You can also sort your results by 'Cheapest,' 'Fastest' or 'Best' flights from William P. Hobby Airport to Chicago Midway International Airport.

Handy information about William P. Hobby Airport (HOU)

  • You'll find HOU at 7800 Airport Boulevard.

  • William P. Hobby Airport scores high marks for on-time performance. 81.06% of flights that depart HOU arrive at their destination on time.

  • Central Houston to William P. Hobby Airport is around 19 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're catching a cab, ride-sharing or driving.

  • The journey when using public transport usually takes 1 hour 40 minutes.

  • Searching for a convenient hotel close to HOU? If you're boarding an early flight from William P. Hobby Airport to Chicago Midway International Airport, these stays will put you moments from your departure gate:

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • The street address for MDW is 5700 South Cicero.

  • Chicago Midway International Airport to central Chicago has a drive time of about 20 minutes. It's approximately 19 kilometres away.

  • Getting to the centre on public transport takes roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • July is the busiest month for flights from William P. Hobby Airport to Chicago Midway International Airport. To avoid the crowds, travel to Chicago in May.

  • The warmest month in Chicago is July, with the temperature ranging between 15ºC and 29ºC. Book your flights from William P. Hobby Airport to Chicago Midway International Airport in this month if this is the type of weather you like.

  • If you like cooler conditions, look for a cheap ticket from HOU to MDW in January. Temperatures average between -12ºC and 3ºC then.

Explore more of United States

  • Columbus is just one of the many cities in United States waiting to be explored once you've seen Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another standout destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without seeing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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