Cheap flights from Houston Hobby Airport to Chicago Midway Airport from $89
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 Hobby Airport to Chicago Midway Airport departing on 5/17. 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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Delta flights from Houston Hobby Airport to Chicago Midway Airport
Our best Delta deals on Houston Hobby Airport to Chicago Midway Airport flight tickets
Southwest flights from Houston Hobby Airport to Chicago Midway Airport
Our best Southwest deals on Houston Hobby Airport to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Houston Hobby Airport 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
What is the typical price of a round-trip flight between Houston Hobby Airport and Chicago Midway Airport?
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 Hobby Airport, with most prices found around $123. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Houston Hobby Airport during the month June is also very affordable. Most momondo users find prices during this month for around $127.
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 Hobby Airport. 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 Hobby Airport 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 Hobby Airport 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 Hobby to Chicago Midway flight route?
Fly from Houston Hobby to Chicago Midway for the best Houston Hobby - 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 Hobby Airport when booking 8 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $219 when searching 8 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Houston Hobby Airport for as low as $139 on momondo.
What cabin class options are available on Houston Hobby to Chicago Midway flights?
There are 1 cabin classes available to choose from on Houston Hobby to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How many flights depart from Houston Hobby Airport to Chicago Midway Airport on average per day?
As of April 2025, 4 flights take off from Houston Hobby Airport and land in Chicago Midway Airport each day. The most common flight departure time for this route is 8:00AM, with 34% of daily flights taking off in the afternoon.
How many flights depart from Houston Hobby Airport to Chicago Midway Airport on average per week?
As of April 2025, 30 flights take off from Houston Hobby Airport and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
When to book flights from Houston Hobby Airport to Chicago Midway Airport
Cheap Houston Hobby Airport to Chicago Midway Airport (HOU to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Houston Hobby Airport to Chicago Midway Airport
How far is Houston Hobby to Chicago Midway by plane?
A flight from Houston Hobby to Chicago Midway will travel around 937.5 mi. A reasonable flight in good conditions will take 2h 25m.
When did momondo last update prices for flights from Houston Hobby Airport to Chicago Midway Airport?
Prices for flights from Houston Hobby Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from Houston Hobby Airport to Chicago Midway Airport?
The number of operators available for flights from Houston Hobby Airport to Chicago Midway Airport is 2 as of April 2025.
How old do you have to be to fly from Houston Hobby Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Houston Hobby Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Houston Hobby Airport to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Houston Hobby Airport to Chicago Midway Airport is Airbus A321neo, representing 17.63% of all bookings. The subsequent popular models are Airbus A320neo at 14.03%, Boeing 737 MAX 8 at 12.32%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 9.57%.
What is the most popular airline from Houston Hobby Airport to Chicago Midway Airport?
Based on momondo bookings for flights between Houston Hobby Airport and Chicago Midway Airport, the leading airline is Frontier, making up 66% of the total bookings. Other popular airlines include Southwest with 34%.
Best airlines flying from Houston Hobby Airport to Chicago Midway Airport
Compare and see reviews for airlines that fly from Houston Hobby Airport to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $64 | Free Cancellation | Rating 6.0 3,281 reviews | |||
| PriceFrom $197 | Free Cancellation | Rating 8.0 4,280 reviews |
Southwest Flights From Houston Hobby Airport to Chicago Midway Airport
Southwest is one of the most popular airlines flying from Houston Hobby Airport to Chicago Midway Airport, operating 30 flights/week on average for this route. A good Southwest flight deal for Houston Hobby Airport to Chicago Midway Airport starts from $197 round-trip, up to an average price of $341. Our users have rated Southwest at 8.0/10.
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Why should I use momondo to find a flight deal from Houston to Chicago?
It is quick and easy to find Houston to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
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?
momondo helps you find the best flight between Houston and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Houston to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Houston and alert you when they change.