Cheap Flights from Houston to Chicago

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Flight deals from Houston to Chicago

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

Find the cheapest month to fly from Houston to Chicago

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

Direct flights from Houston to Chicago

Alternative Houston to Chicago routes

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

Houston to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs11,351
Cheapest month to flyMay
Average flight time2 hrs, 34 mins
Most popular airlineAmerican Airlines
Average flights per week576

Finding cheap flights from Houston 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 to Chicago is Rs26,666. 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 34 minutes is the average flight time from Houston to Chicago.
American Airlines, Southwest Airlines and United fly direct from Houston to Chicago.
As of April 2025, there are 576 flights per week flying from Houston to Chicago.
The cheapest month to fly from Houston to Chicago is usually April 2025.
If you're flying from Houston, 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 Rs26,666.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Houston to Chicago on Wednesday, 14 May 2025.
Yes – the average flight time is 2 hours and 34 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 April, the average temperature is usually around 8°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.
The cheapest airline that flies to Chicago is Frontier Airlines .

Flying from Houston to Chicago: what you need to know

  • Kick off your travels at one of Houston's main airports, George Bush Intercontinental Airport (IAH) or William P. Hobby Airport (HOU). Check out your options for booking a flight from Houston to Chicago departing from either of these.

  • When it comes to arriving in Chicago, O'Hare International Airport (ORD) is a major hub. Chicago Midway International Airport (MDW) is another.

  • Around 2 hours 35 minutes is how long you can expect to be travelling on a direct Houston to Chicago flight.

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

  • George Bush Intercontinental Airport (IAH) to O'Hare International Airport (ORD) is the most traveled route between these two cities. There are 103 weekly departures to choose from. If you have things to finalize before heading off, the last flight from Houston to Chicago is with Spirit Airlines at 22:27. Choose the first IAH to ORD departure operated by United Airlines at 05:00 to make the most of your arrival in Chicago.

  • To ensure you don't miss your Houston to Chicago flight, leave enough time to check in and find your gate. Arriving two hours ahead of international departures and one hour before domestic flights is the standard rule.

  • If you're flying during a popular month like July, be at the airport even earlier. It's wise to arrive up to four hours before an international flight and two hours ahead of a domestic departure. Check-in and security lines are longer during peak periods like Thanksgiving, Christmas and New Year.

How to find the cheapest flights from Houston to Chicago

  • Right now, Rs11,351 is the lowest price we've seen for a one-way ticket from Houston to Chicago. The cheapest price for a return flight is Rs26,666. Remember fares can change due to availability at the time of booking.

  • To secure cheap Houston to Chicago flights, book your trip two months before your planned departure.

  • May is the best month for picking up a fantastic deal on a plane ticket from Houston to Chicago. If you need to travel during a different time of year, the 'Whole month' tool will show you the lowest prices for every month.

  • Snapping up a cheap flight from Houston to Chicago is easy with Price Alerts. All you need to do is set up one of these automatic alerts and we'll let you know as soon as there's a better deal.

  • Tailor your trip using filters. Pick your departure and arrival times, airlines and total journey duration. You can also sort your results by 'Cheapest,' 'Fastest' or 'Best' Houston to Chicago flights.

Flying from Houston

George Bush Intercontinental Airport (IAH)

William P. Hobby Airport (HOU)

  • You can catch a direct flight from Houston to Chicago leaving from William P. Hobby Airport (HOU). Kick off your travels at HOU and come in for landing at Chicago Midway International Airport (MDW).

  • Southwest Airlines offers direct Houston to Chicago plane tickets from HOU. Book your favourite aisle (or window) seat and get to your destination in a single stretch.

  • You can reach HOU from central Houston in about 20 minutes by car, depending on traffic conditions. The journey on public transport takes roughly 1 hour 40 minutes to cover the 16 kilometres or so.

  • Want to enjoy an extra night away before boarding your flight from Houston to Chicago? Relax in a hotel near William P. Hobby Airport before your trip officially starts. Check out these accommodation options:

  • The majority of flights that leave William P. Hobby Airport touch down at their destination as planned. It boasts a strong on-time performance rate of 81.06%.

  • You'll find HOU at 7800 Airport Boulevard.

Arriving in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is approximately 26 kilometres from the centre of Chicago. If you're catching a cab or a ride-share, the drive takes around 35 minutes.

  • It typically takes 55 minutes to get there when travelling by public transport.

  • If you're arriving on a late flight from Houston to Chicago, few things beat the convenience of staying close to the terminal. Collect your bags from the carousel and then be showered and resting soon after at one of these hotels near ORD:

  • Grab an O'Hare International Airport rental car and explore Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are leading providers to choose from here.

  • Booking your vehicle from O'Hare International Airport around four weeks ahead can help you get the best possible rate.

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

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is about 14 kilometres from central Chicago. Once you've disembarked your flight from Houston to Chicago, it takes approximately 20 minutes to get to the heart of the city in a ride-share or cab.

  • The journey will take about 45 minutes on public transport.

  • You'll find some comfortable places to call home for the night near MDW. Settle in and get cosy after your Houston to Chicago flight at any of these well-located options:

  • Forget about inconvenient public transport schedules or waiting forever for a cab. Pick up a Chicago Midway International Airport rental car and take your trip in whatever direction you choose. Check out the availability and rates from Dollar, Hertz and Budget.

  • Get the pick of the lot. Booking your ride from MDW four weeks ahead of time often means better prices and a wider range of vehicles.

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

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Houston to Chicago and go straight to your hotel or start taking in the sights right away. Central Chicago is around 129 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to drive there.

  • Public transport will get you there in around 4 hours 15 minutes.

  • Start your travels without worrying about how to get to your destination with a Chicago Rockford International Airport rental car. Find your perfect set of wheels with reliable names here like Budget, Alamo and National.

  • Booking at least a few weeks in advance of your flight from Houston to Chicago is a smart move. Along with more affordable prices, you'll be able to choose the vehicle make and model you prefer at RFD.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • January is the quietest month for flights from Houston to Chicago, while August is the most popular. Pick the best time to visit Chicago based on whether you prefer a laid-back vibe or a lively atmosphere.

  • Lock in a Houston to Chicago ticket departing in July if you want to experience the city during its warmest month. You can expect temperatures in Chicago to range from 15ºC to 29ºC.

  • January sees average temperatures of between -12ºC and 3ºC. Look for cheap flights from Houston to Chicago around that time if you like cooler conditions.

More about Chicago

  • When it comes to looking for somewhere to lay your head, you'll find the most popular stays in Chicago right here. Browse these options once you've locked in your flight from Houston to Chicago:

  • There are so many things to do and see in this city it can be hard to work out where to begin. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are highlights which should be on every Chicago itinerary.

Explore more of United States

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

  • Indianapolis is another sought-after destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without experiencing 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.