Cheap flights from Houston to Chicago Midway Airport from $43
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 Midway Airport departing on 7/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Round-trip
1 adult
Economy
0 bags
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Cheap round-trip flights
KAYAK's recommended round-trip deals from the most popular airlines that fly from Houston to Chicago.
Cheap one-way flights
Flying one-way? These are some of the best deals recently discovered on momondo for flights from Houston to Chicago.
Cheap last minute flights
Planning a quick getaway from Houston to Chicago? These are the last-minute flight deals available now.
Cheap direct flights
If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.
Southwest flights from Houston to Chicago Midway Airport
Our best Southwest deals on Houston to Chicago Midway Airport flight tickets
Southwest![Southwest]()
May 13![Southwest]()
May 17
HOU5:45 pmHouston Hobby
2h 30m
MDW8:15 pmChicago Midway
MDW8:30 pmChicago Midway
2h 45m
HOU11:15 pmHouston Hobby
Southwest![Southwest]()
Apr 23![Southwest]()
Apr 30
HOU8:20 pmHouston Hobby
2h 30m
MDW10:50 pmChicago Midway
MDW6:30 amChicago Midway
2h 40m
HOU9:10 amHouston Hobby
Frontier flights from Houston to Chicago Midway Airport
Our best Frontier deals on Houston to Chicago Midway Airport flight tickets
Frontier![Frontier]()
May 7![Frontier]()
May 12
IAH10:40 amHouston George Bush Intcntl
2h 37m
MDW1:17 pmChicago Midway
MDW3:49 pmChicago Midway
3h 01m
IAH6:50 pmHouston George Bush Intcntl
Frontier![Frontier]()
Jul 16![Frontier]()
Jul 23
IAH7:45 pmHouston George Bush Intcntl
2h 38m
MDW10:23 pmChicago Midway
MDW4:01 pmChicago Midway
2h 57m
IAH6:58 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 June is also very affordable. Most momondo users find prices during this month for around $130.
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 $297. 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 $456.
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 $123 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $204. 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 3 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $215 when searching 3 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 $126 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 Allegiant Air 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 82% 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 April 2025, there are 5 flights per day flying from Houston to Chicago Midway Airport. The most common time of day flights depart is 5:00AM, with 33% of flights taking off at noon.
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 35 per week as of April 2025. The most frequent departure day is Wed, with 23% 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 April 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 $62 | Free Cancellation | Rating 5.9 3,276 reviews | |||
| PriceFrom $195 | Free Cancellation | Rating 8.0 4,274 reviews | |||
| PriceFrom $196 | Free Cancellation | Rating 8.0 7,897 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
Munster
Crown Point
Monticello
Chesterton
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Porter
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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