Cheap Flights from Houston Hobby to Chicago

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Flight deals from Houston Hobby to Chicago

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

Find the cheapest month to fly from Houston Hobby to Chicago

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

Direct flights from Houston Hobby to Chicago

Alternative Houston Hobby to Chicago routes

Looking for the cheapest, fastest or easiest route from Houston Hobby to Chicago? You could fly into the following airports instead.

Houston to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 1,267
Cheapest month to flyAugust
Average flight time2 hrs, 26 mins
Most popular airlineSouthwest Airlines
Average flights per week40

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Houston Hobby to Chicago is R 2,535. 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.
Southwest Airlines flies direct from Houston Hobby to Chicago.
As of June 2025, there are 40 flights per week flying from Houston Hobby to Chicago.
The cheapest month to fly from Houston Hobby to Chicago is usually June 2025.
If you're flying from Houston Hobby Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from R 2,535.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Houston Hobby Airport to Chicago 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 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.
In June, the average temperature is usually around 19°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago.

Travelling from William P. Hobby Airport (HOU) to Chicago: what you need to know

  • Chicago's timezone is UTC-5, which is the same as Houston (the location of William P. Hobby Airport).

  • The busiest route is from William P. Hobby Airport (HOU) to Chicago Midway International Airport (MDW). Choose from 22 services every week between these two airports. If you want to get on your way as soon as you can, the earliest flight from HOU to MDW is the 05:20 Southwest Airlines service. If you'd rather fly out later on, the final departure is at 22:45 with Southwest Airlines.

  • To avoid rushing for your HOU to Chicago flight, leave plenty of time to check in and find your gate. Arriving two hours before international departures and an hour before domestic flights is the general travel rule.

  • Delays at check-in and security are likely if you're travelling during high season, so give yourself a little extra breathing room. A good rule for peak times? Arrive up to four hours early for international flights and two hours for domestic departures.

  • You can book a direct William P. Hobby Airport to Chicago ticket. Start your trip at HOU and touch down at Chicago Midway International Airport (MDW).

  • Book your ticket with Southwest Airlines. This leading carrier operates direct flights from William P. Hobby Airport to Chicago.

  • HOU is about 16 kilometres from central Houston. If you're driving, ride-sharing or catching a cab from the centre, it'll take you 20 minutes or so to get there, depending on the traffic. If you're taking public transport, expect the travel time to be around 1 hour 40 minutes.

  • Planning to catch an early flight from William P. Hobby Airport to Chicago? Avoid the last-minute rush to the terminal (and sneak in some extra precious sleep) by choosing one of these hotels near HOU:

  • William P. Hobby Airport maintains a strong on-time record, so flight disruptions are less likely. Departures from HOU make it to their destination as scheduled 81.06% of the time.

  • HOU is located at 7800 Airport Boulevard.

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

  • R 1,267 is currently the best price for a one-way William P. Hobby Airport to Chicago flight. Return flight tickets start at R 2,535. These prices may change depending on availability.

  • Get cheap flights from HOU to Chicago by booking one month ahead. According to our research, that's the best time for picking up a bargain.

  • May is the best month for picking up an awesome deal on William P. Hobby Airport to Chicago tickets. If you need to travel during a different time of year, the 'Whole month' tool will give you the lowest prices for every month.

  • You don't need to check back constantly to find out if fares have dropped when you create a Price Alert. We'll let you know when there's an extra saving on cheap flights from HOU to Chicago.

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

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 40 kilometres from the centre of Chicago. If you're grabbing a cab or a ride-share, the drive takes roughly 35 minutes.

  • Travelling on public transport takes about 55 minutes.

  • The last thing you want is a lengthy journey to your hotel if you're arriving on a late flight from William P. Hobby Airport to Chicago. Reserve one of these accommodation options near ORD instead:

  • Get on the fast track to adventure by picking up an O'Hare International Airport rental car. Grab your wheels from Routes Car Rentals, Dollar or Budget and experience the lesser-explored corners of Chicago and beyond.

  • To secure the lowest price, book your ride from O'Hare International Airport around four weeks in advance of your flight from HOU to Chicago.

  • The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is around 19 kilometres from Chicago Midway International Airport (MDW). After your flight from William P. Hobby Airport to Chicago has landed and you've navigated your way to arrivals, expect a drive of around 20 minutes.

  • You can expect the trip to take about 45 minutes on public transport.

  • After stepping off your HOU to Chicago flight, tuck yourself in at a hotel near MDW. These are some comfortable options that'll help you switch to relaxation mode:

  • Forget about inconvenient public transport timetables or waiting forever for a cab. Grab a Chicago Midway International Airport rental car and let your trip unfold on your terms. Compare rates and availability from Dollar, Hertz and Budget.

  • Get the lowest price by securing your ride from MDW four weeks ahead of time. You can also expect to have a wider selection of vehicles.

  • You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Step off your flight from William P. Hobby Airport to Chicago and make your way to your hotel or start taking in the sights right away. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 25 minutes to reach by car.

  • The journey will take roughly 4 hours 15 minutes when travelling on public transport.

  • Enjoy a more relaxed start to your break by checking in to a hotel near RFD after your HOU to Chicago flight. Unwind after a day of travel or simply take a moment to find your footing in a new city at:

  • Start your journey without worrying about how to reach your destination with a Chicago Rockford International Airport rental car. You can book your wheels with trusted suppliers here like Budget, Alamo and National.

  • If you're looking for a specific model or make, booking early gives you a better shot at getting what you want. Secure your ride from RFD a couple of weeks ahead of your flight from William P. Hobby Airport to Chicago.

  • Chicago Rockford International Airport's address is 2 Airport Cir.

Best time to go to Chicago

  • Before scheduling your flights from William P. Hobby Airport to Chicago, consider which time of year is best for you. Peak season in Chicago offers a bustling atmosphere and plenty of things to do, while low season brings cheaper hotel rates and smaller crowds.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your William P. Hobby Airport to Chicago flight ticket then if that's your ideal forecast.

  • If you'd rather travel in cooler conditions, search for a cheap ticket from HOU to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of United States

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

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Experience major highlights starting with 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.