Cheap Flights from Houston to Chicago Midway

Compare Houston to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Houston to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Houston to Chicago Midway Airport? If you want to travel next month, return fares start from $242. Find the lowest prices on one-way and return tickets right here.

Chicago.$242 per passenger.Departing Thu, 9 Apr, returning Mon, 13 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Thu, 9 Apr, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 13 Apr, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $242, select.

Chicago.$258 per passenger.Departing Tue, 31 Mar, returning Fri, 3 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Tue, 31 Mar, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 3 Apr, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $258, select.

Chicago.$269 per passenger.Departing Fri, 1 May, returning Wed, 6 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Fri, 1 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 6 May, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $269, select.

Chicago.$276 per passenger.Departing Fri, 10 Apr, returning Mon, 13 Apr.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Houston George Bush Intercntl. on Fri, 10 Apr, arriving in Chicago Midway.Inbound 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 $276, select.

Chicago.$302 per passenger.Departing Wed, 29 Apr, returning Mon, 4 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Wed, 29 Apr, arriving in Chicago Midway.Inbound 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 $302, select.

Chicago.$304 per passenger.Departing Wed, 27 May, returning Thu, 4 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Wed, 27 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 4 Jun, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $304, select.

Chicago.$306 per passenger.Departing Fri, 8 May, returning Sat, 9 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Fri, 8 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 9 May, arriving in Houston Hobby.Price includes taxes and charges.From $306, select.

Chicago.$330 per passenger.Departing Tue, 28 Apr, returning Sat, 2 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Tue, 28 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 2 May, arriving in Houston Hobby.Price includes taxes and charges.From $330, select.

Chicago.$337 per passenger.Departing Wed, 25 Mar, returning Tue, 31 Mar.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Wed, 25 Mar, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 31 Mar, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $337, select.

Chicago.$340 per passenger.Departing Sat, 6 Jun, returning Tue, 9 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Sat, 6 Jun, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 9 Jun, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $340, select.

Chicago.$366 per passenger.Departing Tue, 31 Mar, returning Sat, 4 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Tue, 31 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 4 Apr, arriving in Houston Hobby.Price includes taxes and charges.From $366, select.

Chicago.$371 per passenger.Departing Fri, 27 Mar, returning Mon, 30 Mar.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Houston George Bush Intercntl. on Fri, 27 Mar, arriving in Chicago Midway.Inbound 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 $371, select.

Chicago.$401 per passenger.Departing Tue, 14 Apr, returning Wed, 1 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Tue, 14 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 1 Jul, arriving in Houston Hobby.Price includes taxes and charges.From $401, select.

Chicago.$401 per passenger.Departing Tue, 14 Apr, returning Wed, 1 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Houston Hobby on Tue, 14 Apr, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Wed, 1 Jul, arriving in Houston Hobby.Price includes taxes and charges.From $401, select.

Chicago.$419 per passenger.Departing Sat, 18 Jul, returning Wed, 22 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Sat, 18 Jul, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 22 Jul, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $419, select.

Chicago.$434 per passenger.Departing Tue, 2 Jun, returning Sat, 6 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Tue, 2 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 6 Jun, arriving in Houston Hobby.Price includes taxes and charges.From $434, select.

Find the cheapest month to fly from Houston to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Houston to Chicago Midway flights are currently cheapest in April.

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Direct flights from Houston to Chicago Midway

Houston to Chicago Midway: Alternative routes

Compare routes from Houston to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Houston to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$242
Cheapest month to fly	April
Average flight time	2 hrs, 29 mins
Most popular airline	Southwest Airlines
Average flights per week	32

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

How much are return flights from Houston to Chicago Midway?

The best price we found for a return flight from Houston to Chicago Midway is $242. 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.

How long does it take to fly from Houston to Chicago Midway?

2 hours and 28 minutes is the average flight time from Houston to Chicago Midway.

Which airlines fly direct from Houston to Chicago Midway?

Southwest Airlines, Frontier Airlines and Volaris fly direct from Houston to Chicago Midway.

How many flights are there a week from Houston to Chicago Midway?

As of March 2026, there are 32 flights per week flying from Houston to Chicago Midway.

When is the cheapest time to fly from Houston to Chicago Midway?

The cheapest month to fly from Houston to Chicago Midway is usually April.

Which upcoming date is cheapest to fly from Houston to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Houston to Chicago Midway Airport on Thursday, 9 April 2026.

Can I get a direct flight from Houston to Chicago Midway Airport?

Yes – the average flight time is 2 hours and 28 minutes.

How can I find the best flight deal to Chicago Midway?

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 Chicago Midway 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.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from Houston to Chicago Midway with?

The cheapest airline that flies to Chicago Midway is Frontier Airlines .

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

Start planning your trip by checking out the ideal departure point for your flight from Houston to Chicago Midway International Airport (MDW). Explore your options for leaving from George Bush Intercontinental Airport (IAH) or William P. Hobby Airport (HOU), the city's main airports.
2 hours 35 minutes is the average journey time for a direct Houston to Chicago Midway International Airport flight.
Chicago Midway International Airport is located in Chicago. The city's timezone is UTC-5, which is the same as Houston.
Your flight from Houston to MDW won't wait if you're late, so get to the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.
Planning to travel during a peak time like public or school holidays? Expect longer queues at check-in and security. Give yourself extra leeway and arrive up to four hours before international flights and two hours before domestic departures.

Airports in Houston

George Bush Intercontinental Airport (IAH)

George Bush Intercontinental Airport (IAH) will have you travelling directly to your destination. Nonstop flights from Houston to Chicago Midway International Airport (MDW) operate out of this terminal.
You'll find a direct flight from Houston to Chicago Midway International Airport with Frontier Airlines. This top carrier offers services from IAH.
Frontier Airlines is the airline with the highest passenger demand for flights from IAH to MDW.
The most reliable carrier for punctuality on this route is Frontier Airlines. Its services land without delay 65.79% of the time.
Located around 27 kilometres from central Houston, IAH can be reached in about 20 minutes by car (depending on traffic). The journey by public transport is roughly 50 minutes.
Have an early flight from Houston to Chicago Midway International Airport? Avoid rushing to the terminal (and get some bonus sleep) by staying at one of these stays near George Bush Intercontinental Airport:
Of the departures from George Bush Intercontinental Airport, 78.42% land on time at their destination.
You'll find IAH at 16930 JFK Boulevard.

William P. Hobby Airport (HOU)

Consider starting your journey from William P. Hobby Airport (HOU). You can book a direct Houston to Chicago Midway International Airport (MDW) flight ticket from this hub.
From HOU, direct flights from Houston to MDW are available with Southwest Airlines.
Southwest Airlines has the largest share of bookings on the HOU to MDW route.
Southwest Airlines is the most punctual carrier flying between William P. Hobby Airport and Chicago Midway International Airport, with 78.62% of its services reaching their destination on time.
HOU is around 19 kilometres from central Houston. It'll take 20 minutes or so to get to the airport driving from the city centre. Public transport takes approximately 1 hour 40 minutes.
Want to treat yourself to an extra night away before boarding your Houston to MDW flight? Unwind in a hotel near William P. Hobby Airport before your adventure officially starts. These stays have your key waiting:
Flights from William P. Hobby Airport have a reputation for punctuality, with 81.06% of them arriving right on cue.
HOU is located at 7800 Airport Boulevard.

About Chicago Midway International Airport (MDW)

If you're arriving on a late flight from Houston to Chicago Midway International Airport, few things beat the convenience of staying close to the terminal. Pick up your bags from the carousel and then be showered and sleeping soon after at one of these hotels near MDW:
Pick up a Chicago Midway International Airport rental car and discover Chicago and beyond with your own set of wheels. Dollar, Hertz and Budget are popular providers you can book with here.
To get the best deal, book your vehicle around four weeks ahead of your Houston to Chicago Midway International Airport flight.
You'll find MDW at 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

The centre of Chicago is roughly 14 kilometres from Chicago Midway International Airport. Travel times by cab or car hire will vary depending on traffic conditions, so do a little research ahead of your trip.
It typically takes 45 minutes to get there using public transport.

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

The lowest price we've found for a one-way ticket from Houston to Chicago Midway International Airport is $118. For a return flight on this route, the best price is $242. Depending on when and how early you book, these fares may change.
Don't leave things to the last minute. You're more likely to find cheap flights from Houston to MDW if you book early. Airlines often offer some amazing early bird rates.
Cheap Houston to Chicago Midway International Airport tickets are easier to find when your dates are flexible. Use the 'Whole month' tool to compare fares throughout the month and then fly out on the cheapest day.
There's no need to check back in every day to find out if prices have dropped when you create a Price Alert. We'll notify you as soon as a lower fare pops up on flight tickets from Houston to MDW.
Save on your flight from Houston to Chicago Midway International Airport by using filters. Select your ideal departure time, duration and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Houston to Chicago Midway International Airport (MDW)

It's time to decide your travel dates for your flight from Houston to Chicago Midway International Airport (MDW). July is when most people travel to Chicago. If a slower pace sounds more appealing, go in May.
The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Book your Houston to MDW flight ticket then if that's your definition of good weather.
Look for cheap tickets from Houston to Chicago Midway International Airport in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC.

More about Chicago

Once you've booked your flight from Houston to Chicago Midway International Airport, find a hotel that offers a good mix of location and comfort. Make one of these options your base for exploring Chicago:
Millennium Park and Lollapalooza are just the start of the top-rated attractions to add to your Chicago must-do list. Keep the momentum going by heading to Art Institute of Chicago.

Explore more of the United States

You've visited Chicago, now it's time to explore other parts of the United States. Journey about 257 kilometres south-east to Indianapolis to tick off its leading sights. From 9-11 Memorial to Lucas Oil Stadium and Eiteljorg Museum, you'll have a full itinerary ahead.
If you're eager to discover another side of the United States, head for Milwaukee, roughly 137 kilometres north of Chicago. Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo are among the biggest draws.