Cheap flights from Houston to Chicago from $71
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Houston to Chicago departing on 10/11. 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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1 adult
Economy
0 bags
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Southwest flights from Houston to Chicago Midway Airport
Our best Southwest deals on Houston to Chicago Midway Airport flight tickets
Southwest![Southwest]()
Sep 4![Southwest]()
Sep 8
HOU5:55 amHouston Hobby
2h 25m
MDW8:20 amChicago Midway
MDW5:45 amChicago Midway
2h 30m
HOU8:15 amHouston Hobby
Southwest![Southwest]()
Sep 4![Southwest]()
Sep 8
HOU5:55 amHouston Hobby
2h 25m
MDW8:20 amChicago Midway
MDW9:30 amChicago Midway
5h 15m
1 stop
HOU2:45 pmHouston Hobby
Delta flights from Houston to Chicago Midway Airport
Our best Delta deals on Houston to Chicago Midway Airport flight tickets
Delta![Delta]()
Sep 3![Delta]()
Sep 10
IAH12:51 pmHouston George Bush Intcntl
5h 46m
1 stop
MDW6:37 pmChicago Midway
MDW6:17 pmChicago Midway
5h 10m
1 stop
IAH11:27 pmHouston George Bush Intcntl
Delta![Delta]()
Sep 3![Delta]()
Sep 6
IAH5:20 amHouston George Bush Intcntl
7h 08m
1 stop
MDW12:28 pmChicago Midway
MDW10:11 amChicago Midway
4h 41m
1 stop
IAH2:52 pmHouston George Bush Intcntl
See travel insights to Chicago from
How to get the cheapest flight ticket from Houston to Chicago Midway 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
Prices
Airlines
Other information
What is the cheapest month to fly to Chicago Midway Airport?
The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Houston, with most prices found around $123. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Houston during the month September is also very affordable. Most momondo users find prices during this month for around $148.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Houston. The lowest ticket price found for a Wednesday departure recently was $267. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Houston because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $447.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Houston at noon is the least expensive time of day to depart. momondo users have found prices as low as $145 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $221. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Houston to Chicago Midway flight route?
Fly from Houston George Bush Intcntl to Chicago Midway for the best Houston - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Houston when booking 13 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $235 when searching 13 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Houston for as low as $127 on momondo.
What cabin class options are available on Houston to Chicago Midway flights?
There are 1 cabin classes available to choose from on Houston to Chicago Midway 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 Houston to Chicago Midway?
Frontier, Southwest, and Delta are the most popular carriers operating from Houston to Chicago Midway
What airlines fly to Chicago Midway Airport?
Frontier, Southwest and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Houston according to our data. Frontier is the first choice among our users, with 72% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Houston to Chicago Midway Airport on average per day?
As of June 2025, there are 6 flights per day flying from Houston to Chicago Midway Airport. The most common time of day flights depart is 8:00AM, with 35% of flights taking off in the afternoon.
How many flights depart from Houston to Chicago Midway Airport on average per week?
The number of flights available between Houston and Chicago Midway Airport is 43 per week as of June 2025. The most frequent departure day is Mon, with 21% of weekly flights leaving on this day.
Cheap Houston to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Houston to Chicago Midway Airport
How far is Houston to Chicago Midway by plane?
Chicago Midway is 932.9 mi away from Houston. Typically, this will take 2h 20m by plane in normal conditions.
When did momondo last update prices for flights from Houston to Chicago Midway Airport?
Prices for flights from Houston to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Houston to Chicago Midway Airport?
As of June 2025, there are 3 operators available to choose from for flights from Houston to Chicago Midway Airport.
How old do you have to be to fly from Houston to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Houston to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
Best airlines flying from Houston to Chicago Midway Airport
Compare and see reviews for airlines that fly from Houston to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $73 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $192 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $196 | Free Cancellation | Rating 8.0 7,946 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsMerrillville
New Buffalo
Hammond
Benton Harbor
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Crown Point
Munster
Monticello
Chesterton
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Saint John
Why use momondo?
Why should I use momondo to find a flight deal from Houston to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Houston to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Houston to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Houston with this policy.
How can momondo help me find flights from Houston to Chicago?
Once all potential Houston to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Houston to Chicago right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Houston to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.
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