Cheap flights from Chicago Midway Airport to Houston from $105
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Houston departing on 12/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Not ready to book? to track prices.Southwest flights from Chicago Midway Airport to Houston Hobby Airport
Our best Southwest deals on Chicago Midway Airport to Houston Hobby Airport flight tickets
Delta flights from Chicago Midway Airport to Houston Hobby Airport
Our best Delta deals on Chicago Midway Airport to Houston Hobby Airport flight tickets
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Use the filters below to find and compare flights from Chicago Midway Airport to Houston Hobby Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Wed 11/11
8:50 pm-11:30 pm
Nonstop2h 40m
Houston Hobby
Wed 11/18
10:00 am-12:25 pm
Nonstop2h 25m
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Wed 11/4
6:40 am-9:20 am
Nonstop2h 40m
Houston Hobby
Sat 11/7
5:00 am-7:25 am
Nonstop2h 25m
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Sat 12/12
6:20 pm-9:05 pm
Nonstop2h 45m
Houston Hobby
Tue 12/15
7:20 am-9:50 am
Nonstop2h 30m
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Wed 11/4
6:40 am-9:20 am
Nonstop2h 40m
Houston Hobby
Wed 11/11
8:40 pm-11:10 pm
Nonstop2h 30m
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Tue 11/17
5:00 pm-7:45 pm
Nonstop2h 45m
Houston Hobby
Tue 11/24
10:30 pm-1:00 am
Nonstop2h 30m
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Tue 11/3
8:50 pm-11:25 pm
Nonstop2h 35m
Houston Hobby
Tue 11/10
8:40 pm-11:10 pm
Nonstop2h 30m
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Sat 11/7
6:20 pm-9:10 pm
Nonstop2h 50m
Houston Hobby
Tue 11/10
7:20 am-9:50 am
Nonstop2h 30m
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Wed 11/11
8:50 pm-11:30 pm
Nonstop2h 40m
Houston Hobby
Sat 11/14
9:45 am-12:10 pm
Nonstop2h 25m
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Wed 11/4
4:19 pm-11:03 pm
1 stop6h 44m
Houston Hobby
Thu 11/12
5:24 pm-10:54 pm
1 stop5h 30m
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Tue 11/10
11:27 am-4:29 pm
1 stop5h 02m
Houston Hobby
Wed 11/18
6:00 am-11:59 am
1 stop5h 59m
See travel insights to Houston from
How to get the cheapest flight ticket from Chicago Midway Airport to Houston Hobby Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Chicago Midway Airport and Houston Hobby Airport?
Prices are currently low for flights on this route.
Typical prices usually range from $254 to $374.The lowest price recently found on this route was $209.
What is the cheapest month to fly to Houston Hobby Airport?
In general, January is the cheapest month to fly from Chicago Midway Airport to Houston Hobby Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $259. The month of November is another great option to travel to Houston Hobby Airport, with average flight prices from Chicago Midway Airport averaging around $268.
What is the cheapest day to depart on your flight to Houston Hobby Airport?
Our data shows that Wednesday is the least expensive day to fly to Houston Hobby Airport. Tickets to fly out on this day can be as low as $364. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Houston Hobby Airport on Monday is $518.
What is the cheapest time of day to depart on your flight to Houston Hobby Airport?
According to our data, the cheapest time of day to fly to Houston Hobby Airport is in the afternoon. momondo users have found flights departing from Chicago Midway Airport to Houston Hobby Airport in the afternoon for as low as $337. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $412. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Chicago Midway to Houston Hobby flight route?
Fly from Chicago Midway to Houston Hobby for the best Chicago Midway - Houston Hobby flight prices
How far in advance should I book a flight from Chicago Midway Airport to Houston Hobby Airport?
You are more likely to see cheaper flights to Houston Hobby Airport from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Houston Hobby Airport for around $353 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Houston Hobby Airport from Chicago Midway Airport for as low as $214 on momondo.
What cabin class options are available on Chicago Midway Airport to Houston Hobby Airport flights?
There is only 1 cabin class available to choose from on Chicago Midway Airport to Houston Hobby Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago Midway to Houston Hobby?
Southwest and Delta are the most popular carriers operating from Chicago Midway to Houston Hobby
What airlines fly to Houston Hobby Airport?
Southwest, Frontier and United Airlines are the top three most popular airlines that fly to Houston Hobby Airport from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 77% of people opting to fly with this airline when traveling to Houston Hobby Airport. Keep in mind that there are 3 different airlines that fly to Houston Hobby Airport on a routine basis, so you have a few additional options to choose from.
How often are flights from Chicago to Houston delayed?
Historically, on average around 21% of flights between Chicago and Houston have experienced a delay on any given week. The average delay length over the past 12 months has been 114 minutes.
What is the most punctual flight time for Chicago to Houston flights?
Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.
What day of the week experiences the fewest flight delays on this route?
Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.
Which airline has the best punctuality record on Chicago to Houston flights?
According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 20% of their flights experiencing any sort of delay.
How many flights depart from Chicago Midway Airport to Houston Hobby Airport on average per day?
3 flights are operational daily from Chicago Midway Airport to Houston Hobby Airport as of October 2026. The most popular departure time for this route is 9:00AM, with 64% of flights per day taking off at noon.
How many flights depart from Chicago Midway Airport to Houston Hobby Airport on average per week?
The number of flights available between Chicago Midway Airport and Houston Hobby Airport is 24 per week as of October 2026. The most frequent departure day is Mon, with 33% of weekly flights leaving on this day.
When to book flights from Chicago Midway Airport to Houston Hobby Airport
Cheap Chicago Midway Airport to Houston Hobby Airport (MDW to HOU) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Houston Hobby Airport
Frequently asked questions about flying from Chicago Midway Airport to Houston Hobby Airport
How far is Chicago Midway to Houston Hobby by plane?
A flight from Chicago Midway to Houston Hobby will travel around 937.5 mi. By plane, this route typically takes 2h 35m.
When did momondo last update prices for flights from Chicago Midway Airport to Houston Hobby Airport?
Prices for flights from Chicago Midway Airport to Houston Hobby Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Houston Hobby Airport?
The number of operators available for flights from Chicago Midway Airport to Houston Hobby Airport is 3 as of October 2026.
How old do you have to be to fly from Chicago Midway Airport to Houston Hobby Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Houston Hobby Airport.
What documentation or ID do you need to fly to Houston Hobby Airport?
The travel and health documents required for your trip to Houston Hobby Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Houston Hobby Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago Midway Airport to Houston Hobby Airport?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Houston Hobby Airport is Airbus A321neo, representing 25.74% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 15.72%, Boeing 737-800 Passenger/BBJ2 (winglets) at 10.20%, and Boeing 737-800 at 9.65%.
What is the most popular airline from Chicago Midway Airport to Houston Hobby Airport?
Based on momondo bookings for flights between Chicago Midway Airport and Houston Hobby Airport, the leading airline is Southwest, making up 77% of the total bookings. Other popular airlines include Frontier with 20% and United Airlines with 3%.
Best airlines flying from Chicago Midway Airport to Houston Hobby Airport
Compare and see reviews for airlines that fly from Chicago Midway Airport to Houston Hobby Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $90 | Free Cancellation | Rating 5.5 2,550 reviews | |||
| PriceFrom $213 | Free Cancellation | Rating 7.4 10,287 reviews | |||
| PriceFrom $224 | Free Cancellation | Rating 7.9 4,214 reviews |
Southwest Flights From Chicago Midway Airport to Houston Hobby Airport
Across 24 Southwest flights from Chicago Midway Airport to Houston Hobby Airport this week, the average price was $383, with the best Southwest deals starting from $224 round-trip. 4,215 users have rated Southwest on momondo, with an average score of 7.9/10.
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Why should I use momondo to find a flight deal from Chicago to Houston?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Houston. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to Houston with flexible booking policies on momondo?
Yes. All flights to Houston from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Chicago to Houston?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Houston from Chicago.
I’m not ready to book a flight from Chicago to Houston right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Chicago to Houston flights. All you need is a valid email address and we will do the rest; it is that quick and easy.