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

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Flight deals from Houston to Chicago Midway

Looking for a cheap last-minute deal or the best round-trip flight from Houston to Chicago Midway Airport? If you want to travel next month, round-trip fares start from $206. Find the lowest prices on one-way and round-trip tickets right here.

Chicago.$205 per passenger.Departing Tue, Sep 1, returning Tue, Sep 8.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Houston Hobby on Tue, Sep 1, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Tue, Sep 8, arriving in Houston Hobby.Price includes taxes and charges.From $205, select.

Chicago.$205 per passenger.Departing Mon, Aug 31, returning Thu, Sep 3.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Houston Hobby on Mon, Aug 31, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Thu, Sep 3, arriving in Houston Hobby.Price includes taxes and charges.From $205, select.

Chicago.$205 per passenger.Departing Sat, Sep 26, returning Sat, Oct 3.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Houston Hobby on Sat, Sep 26, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sat, Oct 3, arriving in Houston Hobby.Price includes taxes and charges.From $205, select.

Chicago.$205 per passenger.Departing Wed, Oct 28, returning Mon, Nov 2.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Houston Hobby on Wed, Oct 28, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Mon, Nov 2, arriving in Houston Hobby.Price includes taxes and charges.From $205, select.

Chicago.$206 per passenger.Departing Sat, Oct 17, returning Wed, Oct 21.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Houston Hobby on Sat, Oct 17, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Wed, Oct 21, arriving in Houston Hobby.Price includes taxes and charges.From $206, select.

Chicago.$206 per passenger.Departing Mon, Aug 10, returning Thu, Aug 13.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Houston Hobby on Mon, Aug 10, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Thu, Aug 13, arriving in Houston Hobby.Price includes taxes and charges.From $206, select.

Chicago.$207 per passenger.Departing Wed, Nov 4, returning Sat, Nov 7.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Houston Hobby on Wed, Nov 4, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sat, Nov 7, arriving in Houston Hobby.Price includes taxes and charges.From $207, select.

Chicago.$209 per passenger.Departing Sat, Jul 25, returning Sat, Sep 5.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Houston Hobby on Sat, Jul 25, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sat, Sep 5, arriving in Houston Hobby.Price includes taxes and charges.From $209, select.

Chicago.$217 per passenger.Departing Tue, Jul 28, returning Thu, Aug 27.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Houston Hobby on Tue, Jul 28, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Thu, Aug 27, arriving in Houston Hobby.Price includes taxes and charges.From $217, select.

Chicago.$219 per passenger.Departing Sat, Dec 12, returning Wed, Dec 16.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Houston Hobby on Sat, Dec 12, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Wed, Dec 16, arriving in Houston Hobby.Price includes taxes and charges.From $219, select.

Chicago.$220 per passenger.Departing Sat, Oct 31, returning Tue, Dec 1.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Houston Hobby on Sat, Oct 31, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Tue, Dec 1, arriving in Houston Hobby.Price includes taxes and charges.From $220, select.

Chicago.$220 per passenger.Departing Tue, Jul 28, returning Tue, Jul 28.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Houston Hobby on Tue, Jul 28, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Tue, Jul 28, arriving in Houston Hobby.Price includes taxes and charges.From $220, select.

Chicago.$245 per passenger.Departing Mon, Jul 27, returning Wed, Jul 29.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Houston Hobby on Mon, Jul 27, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Wed, Jul 29, arriving in Houston Hobby.Price includes taxes and charges.From $245, select.

Chicago.$263 per passenger.Departing Wed, Dec 16, returning Wed, Jan 6.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Houston Hobby on Wed, Dec 16, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Wed, Jan 6, arriving in Houston Hobby.Price includes taxes and charges.From $263, select.

Chicago.$276 per passenger.Departing Sat, Jul 11, returning Wed, Oct 7.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Houston George Bush Intercntl. on Sat, Jul 11, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Wed, Oct 7, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $276, select.

Chicago.$288 per passenger.Departing Wed, Dec 2, returning Sun, Dec 6.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Houston Hobby on Wed, Dec 2, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sun, Dec 6, arriving in Houston Hobby.Price includes taxes and charges.From $288, 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 September.

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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	$205
Cheapest month to fly	August
Average flight time	2 hrs, 41 mins
Most popular airline	Southwest Airlines
Average flights per week	34

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

How much are round-trip flights from Houston to Chicago Midway?

The best price we found for a round-trip flight from Houston to Chicago Midway is $205. 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 40 minutes is the average flight time from Houston to Chicago Midway.

Which airlines fly direct from Houston to Chicago Midway?

Southwest Airlines and United fly direct from Houston to Chicago Midway.

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

There are 34 flights per week flying from Houston to Chicago Midway, as of July 2026.

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

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

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 Monday, August 31, 2026.

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

Yes – the average flight time is 2 hours and 40 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 with from Houston to Chicago Midway?

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

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

Start your trip planning by checking out the best place to catch your flight from Houston to Chicago Midway International Airport (MDW). Explore your options for setting off from Houston George Bush Intercontinental Airport (IAH) or Houston 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's timezone is UTC-6, which is the same as Houston. Chicago Midway International Airport is located in Chicago.
To ensure you get on your flight from Houston to MDW, allow plenty of time to check in and drop off your luggage. Arriving two hours before international departures and one hour before domestic flights is the standard rule.
With more travelers during busy months like July, get to the terminal earlier than usual. Two hours for domestic flights and as much as four for international journeys will help you deal with longer queues. Remember things also get busy during major holidays like Fourth of July.

Airports in Houston

Houston George Bush Intercontinental Airport (IAH)

Take the express route from Houston George Bush Intercontinental Airport (IAH). Direct flights from Houston to Chicago Midway International Airport (MDW) can be booked from here.
When jetting out of IAH, you can take a direct flight from Houston to Chicago Midway International Airport with Frontier Airlines.
Most passengers prefer to fly with Frontier Airlines between IAH and MDW.
The carrier with the best punctuality score on this route is Frontier Airlines. Its services arrive as planned 70.45% of the time.
Traveling from central Houston to IAH takes about 1 hour 10 minutes by public transport. If you drive, ride-share or get a cab, you'll cover the 40 kilometers in 30 minutes or so, depending on traffic.
Catching an early flight from Houston to Chicago Midway International Airport? Avoid the mad dash to the terminal (and sneak in some extra precious sleep) by choosing one of these stays close to Houston George Bush Intercontinental Airport:
When it comes to Houston George Bush Intercontinental Airport's on-time performance, data shows 79% of flights arrive within the expected time frame.
IAH is located at 16930 JFK Boulevard.

Houston Hobby Airport (HOU)

You can book a direct Houston to Chicago Midway International Airport (MDW) plane ticket with departures from Houston Hobby Airport (HOU). Work out whether departing from HOU makes the most sense for you.
Take a direct flight from Houston to MDW with Southwest Airlines. This is one of the leading airlines flying this route out of HOU.
On the HOU to MDW route, Southwest Airlines is the top airline in terms of bookings.
The most punctual carrier is Southwest Airlines. Its Houston Hobby Airport to Chicago Midway International Airport flights land as planned 76.69% of the time.
On public transport, you can travel from central Houston to HOU in about 50 minutes. The terminal is roughly 19 kilometers away, and getting there by car will take approximately 20 minutes.
Catching an early morning flight? You might like to check in to one of these accommodation options near Houston Hobby Airport the day before your Houston to MDW flight:
79% of all departures from Houston Hobby Airport make it to their destination as expected.
HOU is located at 7800 Airport Boulevard.

About Chicago Midway International Airport (MDW)

The last thing you need is a long journey to your hotel if you're getting in late on a flight from Houston to Chicago Midway International Airport. Make yourself comfy at one of these accommodation options near MDW instead:
Booking your vehicle around four weeks ahead of your Houston to Chicago Midway International Airport flight can help you lock in a great deal.
MDW is located at 5700 South Cicero.

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

Chicago Midway International Airport is around 16 kilometers from central Chicago. It takes around 25 minutes or so to drive to the city.
Traveling by public transport takes around 30 minutes.

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

Right now, $96 is the best price we've found for a one-way ticket from Houston to Chicago Midway International Airport. The cheapest price for a return flight is $205. Keep in mind fares can change due to availability at the time of booking.
Don't leave everything to the last minute. You're more likely to walk away with cheap flights from Houston to MDW if you book ahead. Airlines often have some great early bird rates.
Cheap Houston to Chicago Midway International Airport tickets are easier to find if you're not locked into specific dates. Try using the 'Whole month' search tool to compare fares across each month and then choose the cheapest day.
Snapping up a cheap plane ticket from Houston to MDW couldn't be easier with Price Alerts. All you need to do is set up one of these automatic alerts and we'll let you know as soon as a better deal is available.
Tailor your trip using filters. Choose your ideal departure and arrival times, total journey duration and airlines. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest' flights from Houston to Chicago Midway International Airport.

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

November is the quietest month for flights from Houston to Chicago Midway International Airport (MDW), while July is the most popular. Work out the ideal time to visit Chicago based on whether you want a bustling atmosphere or a more laid-back vibe.
When booking your Houston to MDW plane ticket, consider the type of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 16ºC (61ºF) to 28ºC (82ºF).
Search for cheap tickets from Houston to Chicago Midway International Airport in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

When it comes to looking for somewhere to lay your head, you'll find the best stays in Chicago right here. Browse these hotels once you've booked your flight from Houston to Chicago Midway International Airport:
Millennium Park and Art Institute of Chicago are a couple of leading attractions to put on your Chicago to-do list. Keep the momentum going by heading to Willis Tower.

Explore more of the United States

Indianapolis is just one of the many cities in the United States waiting to be discovered after you've seen Chicago. Around 257 kilometers away to the southeast, its top attractions include Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.
Around 137 kilometers north of Chicago, Milwaukee is another favorite stop in the United States. No visit is complete without checking out Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.