$78 Cheap Flights from Houston (HOU) to Chicago (MDW)

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Houston (HOU) to Chicago (MDW) at a glance

Travel between Houston (HOU) and Chicago (MDW) with a variety of airlines offering one-way flights on this popular domestic route. Explore options ranging from full-service to low-cost carriers to find the cheapest flights from Houston to Chicago that align with your travel preferences and schedule. As you prepare to experience Chicago's renowned attractions and vibrant neighborhoods, discover essential information about flights departing from William P. Hobby Airport to Midway International Airport.

• Fastest flight duration: around 2h 30m non-stop
• Route distance: roughly 900 miles (1,450 km)
• Flights per week: around 20+ flights with multiple daily departures on average
• Typical fares (one-way): economy tickets often range from $80–$440, depending on seasonality and how far ahead you book

Flights from William P. Hobby Airport (HOU) to Midway International Airport (MDW)

Based on the latest traveler bookings, here are the top airlines favored for flights from Houston to Chicago, typically featuring non-stop and one-stop options. Popular layovers include Love Field Airport (DAL) with about a 1-hour wait, Louis Armstrong New Orleans International Airport (MSY) with a layover of around 3 hours and 30 minutes, and Hartsfield-Jackson Atlanta International Airport (ATL) with a 2-hour stop. These choices allow you to mix and match price, total travel time, and cabin class to find your ideal itinerary.

• Southwest Airlines: This budget-friendly airline provides both non-stop and one-stop options, with one-way fares generally between $80 and $440. It dominates the route, accounting for about 99% of departures, and offers a non-stop flight duration of approximately 2 hours and 30 minutes.
• Delta: As a full-service airline, Delta offers one-stop flights with one-way prices typically falling in the $105 to $440 range. It represents around 1% of departures on this route, featuring an in-flight duration of 3 hours and 30 minutes, leading to a total travel time of about 5 hours, including layover.

Best time to fly from Houston (HOU) to Chicago (MDW)

The most popular months for travelers flying from Houston to Chicago are March, April, and July, when peak temperatures in Chicago reach up to 73.4°F in July. If you prefer quieter travel, consider November, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 42.3°F. For better deals, August usually offers the lowest average one-way fare around $185. Flight availability peaks in July, with approximately 25 flights per week, making it easier to find convenient departure times. January and February have the fewest flights, with approximately 16 flights per week.

• Cheapest time to fly: August usually offers good deals with average one-way fare around $185, roughly 9% cheaper than the yearly average.
• More budget-friendly months to fly: October, November, and January typically offer average one-way fares of around $192.
• Most flight options: July has the highest number of flights from Houston to Chicago, with approximately 25 flights per week, giving you more flexibility in scheduling your trip.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative routes from Houston (HOU) to Chicago (MDW)

• Houston to Chicago (HOU-ORD): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). One-way economy tickets for this route generally fall between $100 and $450, influenced by the season and time of booking. This journey usually features one-stop options, with popular layover points at Love Field Airport (DAL) and Dallas-Fort Worth International Airport (DFW). Major airlines that operate this route include low-cost carrier Southwest Airlines and American Airlines.
• Houston to Chicago (IAH-ORD): George Bush Intercontinental Airport (IAH) sits about 23 miles away from William P. Hobby Airport (HOU), while O'Hare International Airport (ORD) is roughly 16 miles from Midway International Airport (MDW). One-way economy fares on this route typically range from $45 to $420, depending on the season and when tickets are purchased. This route offers both non-stop and one-stop flight options. Leading airlines for this route are United and American Airlines, with first-class service available as well.
• Houston to Chicago (IAH-MDW): George Bush Intercontinental Airport (IAH) is located around 23 miles from William P. Hobby Airport (HOU). One-way economy fares on this route generally range from $40 to $240, influenced by the time of year and booking period. This route provides both non-stop and one-stop travel options. The primary airlines operating this route include low-cost carrier Frontier Airlines and Delta.

How to find the best prices for flights from Houston (HOU) to Chicago (MDW)

Getting some of the best deals on flights from Houston to Chicago is all about timing and flexibility. Here are some key tips to help you save:

1. Best times to book and fly: cheaper fares are typically found when booking at least two months in advance, although most travelers tend to book between two to eight weeks ahead. Morning departures from 5 a.m. to 12 p.m. usually offer lower prices and are popular among travelers, while flying on Wednesday often results in cheaper fares, even though Friday is the most favored travel day.
2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Midway International Airport from William P. Hobby Airport

Chicago welcomes travelers from Houston with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
• Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International Airport on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
• Public transportation: From Midway International Airport, travelers can find Midway Station, a metro station, just 0.2 miles away on foot, while Chicago Ashburn Station, a train station, is approximately 4.1 miles away by car. For those needing sea access, Lyons Seaport, a seaport, is located about 7.2 miles from the airport by car.

Houston to Chicago Flights

The cheapest times to fly from Houston to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Houston to Chicago are during the month of January. You can find some of the cheapest flights from Houston to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Houston to Chicago

Sunday is one of the best days to book for cheap flights from Houston to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Houston to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Houston to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $78 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Houston to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Houston to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently Asked Questions

How much does a flight from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.) cost?

You can find cheap one-way flights from $78 and cheap return flights $155 Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights typically cost between $169 and $548, and return flights often range between $285 and $898. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.

*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.

What is the cheapest month to fly from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

September is the cheapest month to fly from Houston (HOU) to Chicago (MDW), with average return fares around $299. This price is about 12% lower than the average for the year, as September often experiences a drop in travel demand after the summer peak. Other budget-friendly months for this route include January and May.

*Averages based on flights available on Expedia in the last year.

Which airlines fly direct from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

Enter HOU to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

What is the cheapest airline that flies from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

Frontier Airlines is one of the cheapest airlines offering connecting flights from Houston (HOU) to Chicago (MDW), starting from around $94. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

*Prices based on flights available on Expedia in the last year.

How do I find cheap flights from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

To find a cheap flight from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

What is the best airline to fly with from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

The best airline to fly with from Houston, TX (HOU) to Chicago, IL (MDW) will differ from traveler to traveler. If you like to fly early, WN offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. WN offers the most daily flights from HOU to MDW, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.

What is the best time to fly from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

For flights from Houston (HOU) to Chicago (MDW), September and May are your best bets. September offers lower fares at around $299, while July and August are popular months for travel. This means you can enjoy good prices and a variety of flight options during these times.

*Prices based on flights available on Expedia in the last year.

How many flights per day from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

You can find approximately 5 nonstop flights per day from William P. Hobby (HOU) to Midway Intl. (MDW). For more options, look at flights that include layovers.

What is the earliest flight from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

The earliest flight from Houston (HOU) to Chicago (MDW) usually leaves at around 5:00 AM, operated by Southwest Airlines. This seasonal service is available in July, making it a convenient option for early travelers heading to the Windy City. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

What are the most popular departure times for flights from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

The most popular departure times for flights from Houston (HOU) to Chicago Midway (MDW) are in the late morning, from 9am to 12pm. About 24% of passengers prefer this time window. Many major carriers, including Southwest Airlines, operate flights during this period. This timing is favored because it allows you to arrive in Chicago with plenty of time to enjoy the afternoon and evening.

How long does it take to fly from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

Flying nonstop from HOU to MDW takes around 2 hours 30 minutes, with the route covering approximately 938 miles. Flights with a layover typically take 5 hours 20 minutes longer than direct options. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.

Can you fly business or first class from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

First class seats are offered on the HOU to MDW route with Delta Air Lines.

How do I earn miles on a Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?

It's easy to earn miles on a Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

What airports do you fly into for Chicago from William P. Hobby (HOU)?

From William P. Hobby (HOU), you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD) in Chicago. Some flights may connect through major hubs like Love Field (DAL), Louis Armstrong New Orleans Intl. (MSY), Evers Intl. (JAN) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Is it cheaper to buy a plane ticket from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.) at the last minute?

Typically, booking a last minute flight from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Is it cheaper to book a Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?

Securing a Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

Can I cancel or change the date of my flight from Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.)?

If you booked your Houston, TX (HOU-William P. Hobby) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.