Cheap Flights from Houston Hobby (HOU) to Chicago Midway (MDW)

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Compare Houston Hobby 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 Cheapest month Find the best route Route info FAQs Tips and advice

Flight deals from Houston Hobby to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Houston Hobby Airport to Chicago Midway Airport? If you want to travel next month, return fares start from £209. Find the lowest prices on one-way and return tickets right here.

Chicago.£104 per passenger.Departing Wed, 30 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Wed, 30 Sep, arriving in Chicago Midway.Price includes taxes and charges.From £104, select.

Chicago.£104 per passenger.Departing Sat, 27 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Sat, 27 Feb, arriving in Chicago Midway.Price includes taxes and charges.From £104, select.

Chicago.£104 per passenger.Departing Thu, 1 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From £104, select.

Chicago.£104 per passenger.Departing Thu, 12 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Thu, 12 Nov, arriving in Chicago Midway.Price includes taxes and charges.From £104, select.

Chicago.£104 per passenger.Departing Tue, 5 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Tue, 5 Jan, arriving in Chicago Midway.Price includes taxes and charges.From £104, select.

Chicago.£105 per passenger.Departing Wed, 9 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Wed, 9 Dec, arriving in Chicago Midway.Price includes taxes and charges.From £105, select.

Chicago.£114 per passenger.Departing Tue, 25 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Tue, 25 May, arriving in Chicago Midway.Price includes taxes and charges.From £114, select.

Chicago.£114 per passenger.Departing Sat, 24 Apr.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Sat, 24 Apr, arriving in Chicago Midway.Price includes taxes and charges.From £114, select.

Chicago.£118 per passenger.Departing Tue, 1 Jun.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Houston Hobby on Tue, 1 Jun, arriving in Chicago Midway.Price includes taxes and charges.From £118, select.

Chicago.£121 per passenger.Departing Sat, 10 Jul.One-way flight with Delta.Outbound indirect flight with Delta, departs from Houston Hobby on Sat, 10 Jul, arriving in Chicago Midway.Price includes taxes and charges.From £121, select.

Chicago.£136 per passenger.Departing Mon, 22 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Mon, 22 Mar, arriving in Chicago Midway.Price includes taxes and charges.From £136, select.

Chicago.£136 per passenger.Departing Tue, 1 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Houston Hobby on Tue, 1 Jun, arriving in Chicago Midway.Price includes taxes and charges.From £136, select.

Find the cheapest month to fly from Houston Hobby to Chicago Midway

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

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Direct flights from Houston Hobby to Chicago Midway

Houston Hobby to Chicago Midway: Alternative routes

Compare routes from Houston Hobby 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	£104
Cheapest month to fly	February
Average flight time	2 hrs, 26 mins
Most popular airline	Southwest Airlines
Average flights per week	34

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

How much are return flights from Houston Hobby to Chicago Midway?

The best price we found for a return flight from Houston Hobby to Chicago Midway is £168. 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 Hobby to Chicago Midway?

2 hours and 26 minutes is the average flight time from Houston Hobby to Chicago Midway.

Which airlines fly direct from Houston Hobby to Chicago Midway?

Southwest Airlines flies direct from Houston Hobby to Chicago Midway.

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

As of September 2026, there are 34 flights per week flying from Houston Hobby to Chicago Midway.

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

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

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

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Houston Hobby Airport to Chicago Midway Airport on Tuesday, 10 November 2026.

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

Yes – the average flight time is 2 hours and 26 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 Hobby Airport to Chicago Midway with?

Currently, Delta and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

Flying from Houston Hobby Airport (HOU) to Chicago Midway Airport (MDW): what you need to know

The average length of a direct flight from Houston Hobby Airport to Chicago Midway Airport is 2 hours 25 minutes.
Houston and Chicago are in the same timezone, UTC-6.
Every week, there are 22 Houston Hobby Airport to Chicago Midway Airport flights. If you want to take off early, take the 05:20 Southwest Airlines flight. If you're eager to make the most of your time before you fly, the latest flight is at 22:45 with Southwest Airlines.
To ensure you get on your HOU to MDW flight, leave enough time for things like check-in and baggage drop. Turning up two hours before international departures and one hour before domestic flights is the standard rule.
Be prepared for longer lines during popular months like July. Arriving up to four hours ahead of an international flight and two hours for domestic departures will give you ample time for security and boarding.
Southwest Airlines has direct flights from Houston Hobby Airport to Chicago Midway Airport. Book with this popular airline, then get ready to discover the sights in Chicago — and maybe even more of the United States if your schedule allows.
Most travellers choose to fly with Southwest Airlines on this route.
With 76.69% of services landing as planned, Southwest Airlines is the most punctual carrier operating HOU to MDW flights.
Think about adding a stopover when booking your ticket from Houston Hobby Airport to Chicago Midway Airport. Simply deselect 'Direct flights only' to break up your journey, or perhaps explore a new destination along the way. Here's where you can stop between HOU and MDW:
- Kansas City International Airport
- Dallas Love Field Airport
- Louisville Muhammad Ali International Airport

Handy information about Houston Hobby Airport (HOU)

You'll find HOU at 7800 Airport Boulevard.
79% of flights departing from Houston Hobby Airport land at their destination on time.
Central Houston to Houston Hobby Airport is approximately 19 kms (12 miles). Depending on traffic, it'll take you about 20 minutes to get there if you're ride-sharing, catching a taxi or driving.
The journey on public transport takes roughly 50 minutes.
Get your journey off to a relaxed start by staying near HOU. Whether you've booked an early flight from Houston Hobby Airport to Chicago Midway Airport or want to avoid feeling rushed, these hotels have you covered:

Arriving at Chicago Midway Airport (MDW)

The last thing you need is a long journey to your hotel if you're arriving on a late Houston Hobby Airport to Chicago Midway Airport flight. Book one of these accommodation options near MDW instead:
Go where the road takes you with a Chicago Midway Airport rental car. Book your wheels from Dollar, Hertz or Budget and discover more of Chicago and beyond.
Lock in the best deal by booking your ride from Chicago Midway Airport around four weeks before your trip.

Getting from Chicago Midway Airport (MDW) to central Chicago

The address for MDW is 5700 South Cicero.
Chicago Midway Airport to the centre of Chicago has a drive time of about 25 minutes. It's approximately 16 kms (10 miles) away.
Travelling on public transport typically takes 30 minutes.

When to fly to Chicago Midway Airport (MDW)

It's time to plan your trip dates for your flight from Houston Hobby Airport to Chicago Midway Airport. July is the busiest month to head to Chicago. If you prefer a more relaxed vibe, go in December.
When reserving your flight from Houston Hobby Airport to Chicago Midway Airport, think about the type of weather you like. July is the warmest month in Chicago, with temperatures ranging from 16ºC to 28ºC.
Look for cheap tickets from HOU to MDW in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

Explore more of the United States

You've done Chicago, now it's time to discover more of the United States. Journey about 451 kms (280 miles) south-east to Columbus to tick off its top sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, you've got a jam-packed schedule ahead.
Indianapolis is another sought-after destination in the United States and is around 257 kms (160 miles) south-east of Chicago. No journey is complete without experiencing Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.