Cheap Flights from Houston Hobby to Chicago

Compare Houston Hobby to Chicago flight deals

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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 Airport to Chicago? If you want to travel next month, return fares start from Rs52,601. 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

Houston to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs23,238
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: 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 Rs46,582. 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 May 2026, there are 31 flights per week flying from Houston Hobby to Chicago.
The cheapest month to fly from Houston Hobby to Chicago is usually July.
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 Rs46,582.
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, 22 July 2026.
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 May, the average temperature is usually around 13°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 Houston Hobby Airport (HOU) to Chicago: what you need to know

  • Houston (the location of Houston Hobby Airport) and Chicago follow the same timezone — UTC-6.

  • With 27 flights a week between the two airports, Houston Hobby Airport (HOU) to Chicago Midway International Airport (MDW) is the busiest route. Southwest Airlines operates the earliest flight at 05:20. If you're eager to get more out of your day before jetting off, the latest flight from HOU to MDW is with Southwest Airlines at 22:45.

  • To avoid missing your HOU to Chicago flight, leave plenty of time to check in and drop off your luggage. Arriving two hours ahead of international departures and an hour before domestic flights is the general travel rule.

  • You'll likely experience longer lines in popular months such as July. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a smart move.

  • You can book a direct Houston Hobby Airport to Chicago ticket. Start your trip at HOU and end it at Chicago Midway International Airport (MDW).

  • Be on the lookout for promotions from Southwest Airlines. This carrier operates direct flights from Houston Hobby Airport to Chicago.

  • Located around 16 kilometres from the centre of Houston, HOU can be reached in about 20 minutes by car, depending on traffic. The journey on public transport takes roughly 50 minutes.

  • Planning to catch an early flight from Houston Hobby Airport to Chicago? Avoid the last-minute rush to the airport (and catch some extra z's) by choosing one of these hotels near HOU:

  • When it comes to the on-time performance of Houston Hobby Airport, data shows 79% of flights complete their journey on time.

  • You'll find HOU at 7800 Airport Boulevard.

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

  • Rs23,238 is currently the best price for a one-way Houston Hobby Airport to Chicago flight. A return plane ticket starts from Rs46,582. These prices can change based on availability.

  • Don't wait until the last moment. You're more likely to find cheap flights from HOU to Chicago if you book early. Airlines often have some amazing early bird deals.

  • If you're willing to be flexible with your travel dates, try using the 'Whole month' search tool. It'll find the lowest price across every month when searching for a Houston Hobby Airport to Chicago ticket.

  • Finding a cheap flight from HOU to Chicago couldn't be easier with Price Alerts. All you need to do is set up one of these automatic notifications and we'll get in touch as soon as a deal gets even better.

  • Pick your ideal arrival and departure times, airlines and number of stops with our filters. Then, sort the results for your flight from Houston Hobby Airport to Chicago by 'Cheapest,' 'Fastest' or 'Best.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) is around 27 kilometres from central Chicago. If you're opting for a ride-share or a taxi, the drive will take roughly 30 minutes.

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

  • If you have a late flight from Houston Hobby Airport to Chicago, nothing beats the convenience of staying close to the terminal. Grab your suitcases from the carousel and then be showered and relaxing not long after at one of these accommodation options near ORD:

  • Lock in the best rate by booking your ride from Chicago 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 16 kilometres from Chicago Midway International Airport (MDW). Once your flight from Houston Hobby Airport to Chicago has hit the runway and you've made your way to arrivals, the drive should take about 25 minutes.

  • Public transport will get you there in about 30 minutes.

  • After stepping off your HOU to Chicago flight, settle in at a hotel close to MDW. These are some great accommodation options that'll help you switch to relaxation mode:

  • Avoid last-minute price surges. Reserving your ride four weeks ahead of your arrival at MDW will help you stay within budget.

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

Chicago Rockford International Airport (RFD)

  • Find your way to the city centre after your flight from Houston Hobby Airport to Chicago has arrived. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to get to by car.

  • Public transport will get you there in about 2 hours.

  • If you don't want to make your way into the centre, head for a hotel close to RFD. Check in to one of these stays after your HOU to Chicago flight:

  • Rental companies sometimes offer promotions on early bookings, so reserve your ride from RFD ahead of your flight from Houston Hobby Airport to Chicago. A bit of planning goes a long way for your wallet.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • It's time to choose your dates for your flight from Houston Hobby Airport to Chicago. July is the most popular month to visit Chicago. If you like a quieter atmosphere, go in January.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC and 28ºC. Book your Houston Hobby Airport to Chicago plane ticket then if this is the type of weather you enjoy.

  • Search for cheap tickets from HOU to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

Explore more of the United States

  • Columbus is just one of the many cities in the United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres away to the southeast, its top attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • If there's time to check out another major stop in the United States, consider Indianapolis, about 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are the start of reasons to visit.

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