Cheap Flights from Chicago to Houston Hobby

Compare Chicago to Houston Hobby flight deals

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

Book the best Houston Hobby fare with no extra fees

Flight deals from Chicago to Houston Hobby

Looking for a cheap last-minute deal or the best return flight from Chicago to Houston Hobby Airport? If you want to travel next month, return fares start from $313. Find the lowest prices on one-way and return tickets right here.

Houston.$311 per passenger.Departing Mon, 31 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 31 Aug, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $311, select.

Houston.$311 per passenger.Departing Mon, 19 Oct, returning Thu, 22 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 19 Oct, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Thu, 22 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $311, select.

Houston.$311 per passenger.Departing Thu, 13 Aug, returning Mon, 17 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 13 Aug, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Mon, 17 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $311, select.

Houston.$311 per passenger.Departing Mon, 14 Sep, returning Mon, 14 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 14 Sep, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Mon, 14 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $311, select.

Houston.$312 per passenger.Departing Thu, 5 Nov, returning Mon, 9 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 5 Nov, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Mon, 9 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $312, select.

Houston.$312 per passenger.Departing Thu, 29 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 29 Oct, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Mon, 2 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $312, select.

Houston.$346 per passenger.Departing Thu, 26 Nov, returning Tue, 1 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 26 Nov, arriving in Houston Hobby.Inbound indirect flight with Delta, departs from Houston Hobby on Tue, 1 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $346, select.

Houston.$363 per passenger.Departing Sat, 25 Jul, returning Sat, 1 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 25 Jul, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Sat, 1 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $363, select.

Houston.$363 per passenger.Departing Wed, 30 Sep, returning Sat, 3 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 30 Sep, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Sat, 3 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $363, select.

Houston.$443 per passenger.Departing Wed, 2 Dec, returning Fri, 4 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 2 Dec, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Fri, 4 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $443, select.

Houston.$450 per passenger.Departing Sat, 25 Jul, returning Sat, 25 Jul.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 25 Jul, arriving in Houston Hobby.Inbound indirect flight with Southwest Airlines, departs from Houston Hobby on Sat, 25 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $450, select.

Houston.$485 per passenger.Departing Tue, 9 Feb, returning Wed, 17 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 9 Feb, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Wed, 17 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $485, select.

Houston.$519 per passenger.Departing Sat, 9 Jan, returning Sat, 23 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 9 Jan, arriving in Houston Hobby.Inbound indirect flight with Delta, departs from Houston Hobby on Sat, 23 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $519, select.

Houston.$521 per passenger.Departing Wed, 16 Dec, returning Sun, 3 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 16 Dec, arriving in Houston Hobby.Inbound indirect flight with Southwest Airlines, departs from Houston Hobby on Sun, 3 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $521, select.

Houston.$535 per passenger.Departing Sat, 9 Jan, returning Sat, 23 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 9 Jan, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Sat, 23 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $535, select.

Houston.$580 per passenger.Departing Thu, 17 Dec, returning Sun, 3 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 17 Dec, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Sun, 3 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $580, select.

Find the cheapest month to fly from Chicago to Houston Hobby

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

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

May

Jun

Direct flights from Chicago to Houston Hobby

Chicago to Houston Hobby: Alternative routes

Compare routes from Chicago 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 found	$311
Cheapest month to fly	August
Average flight time	2 hrs, 38 mins
Most popular airline	Southwest Airlines
Average flights per week	39

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

How much are return flights from Chicago to Houston Hobby?

The best price we found for a return flight from Chicago to Houston Hobby is $311. 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.

How long does it take to fly from Chicago to Houston Hobby?

2 hours and 38 minutes is the average flight time from Chicago to Houston Hobby.

Which airlines fly direct from Chicago to Houston Hobby?

Southwest Airlines flies direct from Chicago to Houston Hobby.

How many flights are there a week from Chicago to Houston Hobby?

As of July 2026, there are 39 flights per week flying from Chicago to Houston Hobby.

When is the cheapest time to fly from Chicago to Houston Hobby?

The cheapest month to fly from Chicago to Houston Hobby is usually August.

Which upcoming date is cheapest to fly from Chicago to Houston Hobby Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Houston Hobby Airport on Thursday, 13 August 2026.

Can I get a direct flight from Chicago to Houston Hobby Airport?

Yes – the average flight time is 2 hours and 38 minutes.

How can I find the best flight deal to Houston Hobby?

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.

When is the best time to book flights to Houston?

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.

Which is the cheapest airline to fly from Chicago to Houston Hobby with?

The cheapest airline that flies to Houston Hobby is Southwest Airlines .

Travelling from Chicago to Houston Hobby Airport (HOU): What you need to know

Your trip gets off the ground at Chicago's main airport, Chicago Midway International Airport (MDW). Explore the options for booking a flight from Chicago to Houston Hobby Airport (HOU) departing from this base.
Houston's timezone is UTC-6, which is the same as Chicago. Houston Hobby Airport is located in Houston.
To ensure you get on your flight from Chicago to HOU, leave enough time for things like baggage drop and finding your gate. Turning up two hours before international departures and an hour before domestic flights is the standard rule.
Flying during a peak month like July? Busy periods (like Christmas/New Year and spring break) can easily add another hour at check-in and security. Be extra safe and arrive up to four hours ahead of international flights and two hours before domestic departures.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

ORD is around 27 kilometres from central Chicago. If you're catching a taxi, driving or ride-sharing from the centre, it'll take you 30 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the trip time to be around 45 minutes.
Booked an early flight from Chicago to Houston Hobby Airport? Avoid the stress of rushing to the terminal (and enjoy a few extra z's) by staying at one of these hotels close to Chicago O'Hare International Airport:
70% of flights that take off from Chicago O'Hare International Airport reach their destination on schedule.
ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Planning to leave from Chicago Midway International Airport (MDW)? Direct Chicago to Houston Hobby Airport (HOU) plane tickets can be booked from this popular hub.
Southwest Airlines operates direct flights from Chicago to HOU departing from MDW. Book your favourite window seat and get to your destination in a single stretch.
On the MDW to HOU route, Southwest Airlines is the preferred choice for many passengers.
With 73.37% of its services landing as planned, Southwest Airlines is the most punctual carrier flying between Chicago Midway International Airport and Houston Hobby Airport.
You can reach MDW from the centre of Chicago in approximately 25 minutes by car, depending on traffic conditions. The ride on public transport will take roughly 30 minutes to travel the 16 kilometres or so.
Want to enjoy an extra night away before your Chicago to HOU flight? Kick back in a hotel near Chicago Midway International Airport before your holiday officially begins. These stays are calling your name:
76% of flights leaving Chicago Midway International Airport meet their expected arrival time.
MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

RFD is around 145 kilometres from central Chicago. Driving from the city centre to the terminal takes about 1 hour 40 minutes. If you're thinking about using public transport, you can expect a journey of around 2 hours.
Sleep a little longer, move a little slower, and still make your Chicago to Houston Hobby Airport flight with time to spare. These accommodation options near Chicago Rockford International Airport make departure day a breeze if you're flying out first thing:
Airports have an on-time performance rating that measures how often flights land without delays. At RFD, that figure is 71%.
The address of Chicago Rockford International Airport is 2 Airport Cir.

About Houston Hobby Airport (HOU)

If you have a late flight from Chicago to Houston Hobby Airport, few things top the convenience of staying close to the terminal. Pick up your bags from the carousel and then be showered and snoozing soon after at one of these hotels near HOU:
Booking your vehicle around four weeks ahead of your Chicago to Houston Hobby Airport flight can help you lock in a great deal.
The street address for HOU is 7800 Airport Boulevard.

Getting from Houston Hobby Airport (HOU) to central Houston

Houston Hobby Airport is around 19 kilometres from the centre of Houston. It takes around 20 minutes or so to drive to the city.
It'll take around 50 minutes when travelling by public transport.

How to find the cheapest flights from Chicago to Houston Hobby Airport (HOU)

Currently, $155 is the lowest price we've found for a one-way ticket from Chicago to Houston Hobby Airport. The cheapest price for a return flight is $311. Keep in mind fares can change due to demand at the time of booking.
To pick up cheap flights from Chicago to HOU, book ahead. Airlines usually offer lower prices when flights are first released.
If you can be flexible with your travel plans, try using the 'Whole month' search tool. It'll give you the lowest price across every month when searching for your Chicago to Houston Hobby Airport ticket.
You don't need to search every day to find out if fares have dropped when you set up a Price Alert. We'll notify you when a new deal shows up on plane tickets from Chicago to HOU.
Filters make it easier to scoop up a deal on your flight from Chicago to Houston Hobby Airport. Choose the airlines, flight times and number of stops that make sense for you. Then sort the results by 'Cheapest' to zero in on the cheapest fare fast.

The best time to fly from Chicago to Houston Hobby Airport (HOU)

Think about the pace you're looking for when deciding when to fly. December is the quietest month to visit Houston. July is when most people book flights from Chicago to Houston Hobby Airport (HOU), which may be ideal if you're chasing more action.
The warmest month in Houston is August, with temperatures ranging between 24ºC and 40ºC. Lock in your Chicago to HOU plane ticket then if you enjoy this type of weather.
If you want to travel in cooler conditions, search for a cheap ticket from Chicago to Houston Hobby Airport in January when temperatures are between 5ºC and 19ºC.

More about Houston

Once you've booked your flight from Chicago to Houston Hobby Airport, find a hotel that puts you in a great location. Make one of these options your base for exploring Houston:
The Museum of Fine Arts, Houston, Beck Building and Houston Museum of Natural Science are just a couple of the top attractions to put on your Houston travel itinerary. Keep the sightseeing going at The Menil Collection.

Explore more of the United States

Houston has its own special appeal, but there are so many other parts of the United States waiting to be explored. Around 241 kilometres west of Houston, a trip to Austin will keep you on the go. Check out popular attractions like Texas State Capitol, Austin Museum of Art, Downtown and 360 Bridge.
If you're ready to explore another well-known destination in the United States, head for Corpus Christi, roughly 290 kilometres southwest of Houston. USS LEXINGTON, Texas State Aquarium and Bayfront Park are highlights.