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Cheap Flights from Chicago Midway to Houston

Compare Chicago Midway to Houston flight deals

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

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Flight deals from Chicago Midway Airport to Houston

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Houston? If you want to travel next month, return fares start from R 1,944. Find the lowest prices on one-way and return tickets right here.
Houston.R 750 per passenger.Departing Mon, 13 Apr.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Mon, 13 Apr, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From R 750, select.
Houston.R 1,223 per passenger.Departing Mon, 1 Jun.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 1 Jun, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From R 1,223, select.
Houston.R 1,228 per passenger.Departing Mon, 4 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 4 May, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From R 1,228, select.
Houston.R 1,516 per passenger.Departing Tue, 12 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 12 May, arriving in Houston Hobby.Price includes taxes and charges.From R 1,516, select.
Houston.R 1,518 per passenger.Departing Tue, 2 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 2 Jun, arriving in Houston Hobby.Price includes taxes and charges.From R 1,518, select.
Houston.R 1,586 per passenger.Departing Mon, 30 Mar.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Mon, 30 Mar, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From R 1,586, select.
Houston.R 2,045 per passenger.Departing Sun, 2 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 2 Aug, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From R 2,045, select.
Houston.R 2,045 per passenger.Departing Mon, 20 Jul.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 20 Jul, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From R 2,045, select.
Houston.R 2,364 per passenger.Departing Tue, 14 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 14 Jul, arriving in Houston Hobby.Price includes taxes and charges.From R 2,364, select.
Houston.R 2,364 per passenger.Departing Thu, 17 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 17 Sep, arriving in Houston Hobby.Price includes taxes and charges.From R 2,364, select.
Houston.R 2,370 per passenger.Departing Thu, 20 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 20 Aug, arriving in Houston Hobby.Price includes taxes and charges.From R 2,370, select.
Houston.R 6,787 per passenger.Departing Mon, 15 Feb.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 15 Feb, arriving in Houston Hobby.Price includes taxes and charges.From R 6,787, select.

Find the cheapest month to fly from Chicago Midway to Houston

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Houston flights are currently cheapest in April.
Mar
from R 1,586
Apr
from R 750
May
from R 1,228
Jun
from R 1,223
Jul
from R 2,045
Aug
from R 2,045
Sep
from R 2,364
Oct
Find prices
Nov
Find prices
Dec
Find prices
Jan
Find prices
Feb
from R 6,787

Direct flights from Chicago Midway to Houston

Alternative Chicago Midway to Houston routes

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

Houston Hobby

16km from central Houston
Closest
from R 1,516
Search flights

Houston George Bush Intercntl.

25km from central Houston
Cheapest
from R 750
Search flights

Houston Ellington Field

28km from central Houston
Search flights

Galveston

74km from central Houston
Search flights

Chicago to Houston: Flight information

The things to know before you go.
Cheapest flight foundR 750
Cheapest month to flyApril
Average flight time2 hrs, 53 mins
Most popular airlineSouthwest Airlines
Average flights per week31

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

There are 4 airports in Houston: Houston Hobby, Houston George Bush Intercntl., Houston Ellington Field, and Galveston.
The best price we found for a return flight from Chicago Midway to Houston is R 1,944. 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 52 minutes is the average flight time from Chicago Midway to Houston.
Southwest Airlines, Frontier Airlines and Volaris fly direct from Chicago Midway to Houston.
As of March 2026, there are 31 flights per week flying from Chicago Midway to Houston.
The cheapest month to fly from Chicago Midway to Houston is usually April.
If you're flying from Chicago Midway Airport, the cheapest airport near Houston is Houston George Bush Intercntl. – which is 25.0 km away from the centre of Houston. We've found flights into this airport from R 1,944.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Houston on Monday, 13 April 2026.
Yes – the average flight time is 2 hours and 52 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 Houston 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 Houston is around 40 days in advance, so don’t leave your flight to the last minute.
In March, the average temperature is usually around 16°C. August is typically the warmest month in Houston, when it usually averages around 34°C. You can expect the least rain in March. The coldest month is January, with temperatures averaging 6°C. The rainiest month is June.
Currently, Frontier Airlines offers the cheapest flight tickets to Houston.

Flying from Chicago Midway International Airport (MDW) to Houston: what you need to know

  • The average duration of a direct flight from Chicago Midway International Airport to Houston is 2 hours 35 minutes.

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

  • The busiest route is from Chicago Midway International Airport (MDW) to William P. Hobby Airport (HOU). There are 22 weekly services between these two airports. If you'd like to get going as soon as possible, the earliest flight from MDW to HOU is the 05:10 Southwest Airlines option. If you'd rather fly out later on, the final departure is at 22:55 with Southwest Airlines.

  • To avoid missing your MDW to Houston flight, leave enough time to check in and find your gate. Turning up two hours ahead of international departures and one hour before domestic flights is the general rule.

  • Longer lines at security and check-in are likely if you're heading away during high season, so allow a little extra breathing room. A good rule for peak times? Get there up to four hours early for international flights and two hours for domestic departures.

  • Begin your journey at MDW and fly straight to George Bush Intercontinental Airport (IAH). That's where you can expect to touch down when searching for Chicago Midway International Airport to Houston tickets.

  • Book your seat with Southwest Airlines. This popular airline offers direct flights from Chicago Midway International Airport to Houston.

  • Travelling from central Chicago to MDW takes about 45 minutes by public transport. If you ride-share, drive or grab a cab, you'll cover the 14 kilometres in 20 minutes or so, depending on traffic conditions.

  • Want a relaxed start to your trip? Stay near MDW. Whether you have an early flight from Chicago Midway International Airport to Houston or don't want departure day to feel hectic, these hotels have you covered:

  • Of all flights leaving Chicago Midway International Airport, 77.88% land on schedule at their destination.

  • You'll find MDW at 5700 South Cicero.

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Houston

  • R 750 is currently the best price for a one-way Chicago Midway International Airport to Houston flight. Return flight tickets start at R 1,944. These fares may change based on availability.

  • Book one month before you travel. Pricing trends suggest that this is the ideal window for finding cheap flights from MDW to Houston.

  • May is the best month for scoring an awesome deal on Chicago Midway International Airport to Houston tickets. If you need to travel at a different time of year, the 'Whole month' tool will give you the lowest prices for each month.

  • There's no need to keep checking in to see if fares have dropped when you create a Price Alert. We'll let you know when there's an updated deal for cheap flights from MDW to Houston.

  • Snag an affordable flight from Chicago Midway International Airport to Houston with the help of our filters. Select your preferred duration, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Houston

George Bush Intercontinental Airport (IAH)

William P. Hobby Airport (HOU)

  • Once your flight from Chicago Midway International Airport to Houston has hit the runway, you can get to the city centre in about 20 minutes by car. Central Houston is roughly 19 kilometres from William P. Hobby Airport (HOU).

  • You can expect the trip to take roughly 1 hour 40 minutes on public transport.

  • Following your MDW to Houston flight, tuck yourself in at a hotel near HOU. These are some great options that'll help you switch to relaxation mode:

  • Forget about inconvenient public transport timetables or waiting in a long cab line. Grab a William P. Hobby Airport rental car and take your trip in whatever direction you choose. Check out the availability and rates from Easirent, Dollar and Thrifty.

  • Score the best price by booking your ride from HOU four weeks in advance. You'll also have access to a greater range of vehicles.

  • William P. Hobby Airport can be found at 7800 Airport Boulevard.

Best time to go to Houston

  • Travel to Houston during high season if you want a bustling atmosphere, but remember that prices may be higher. Alternatively, book flights from Chicago Midway International Airport to Houston in the off-season when prices are cheaper and it's not as busy.

  • Before locking in your Chicago Midway International Airport to Houston flight ticket, think about what kind of weather you prefer. August is the warmest month in Houston, with temperatures ranging from 24ºC (75ºF) to 40ºC (104ºF).

  • January has average temperatures of between 5ºC (41ºF) and 19ºC (66ºF). Search for a cheap ticket from MDW to Houston around that time if you'd rather travel in cooler conditions.

More about Houston

Explore more of United States

  • San Antonio is just one of the many cities in United States waiting to be explored after you've experienced Houston. Around 306 kilometres away to the west, check out popular attractions including The San Antonio River Walk, San Antonio Missions National Historical Park and San Fernando Cathedral.

  • If you want to check out another side of United States, consider Dallas, roughly 370 kilometres north of Houston. Dallas Arboretum and Botanical Gardens, Perot Museum of Nature and Science and Dallas Museum of Art are key highlights.

Plan the rest of your trip from Chicago to Houston

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