Cheap Flights from Houston George Bush Intercntl. to Chicago Midway

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Compare Houston George Bush Intercntl. 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 George Bush Intercntl. to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Houston George Bush Intercntl. Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $384. Find the lowest prices on one-way and return tickets right here.

Chicago.$323 per passenger.Departing Tue, 10 Nov, returning Wed, 11 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Tue, 10 Nov, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 11 Nov, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $323, select.

Chicago.$324 per passenger.Departing Mon, 28 Sep, returning Sat, 10 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Mon, 28 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 10 Oct, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $324, select.

Chicago.$329 per passenger.Departing Fri, 30 Oct, returning Wed, 4 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Fri, 30 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 4 Nov, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $329, select.

Chicago.$388 per passenger.Departing Tue, 20 Oct, returning Tue, 20 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Houston George Bush Intercntl. on Tue, 20 Oct, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 20 Oct, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $388, select.

Chicago.$389 per passenger.Departing Sat, 19 Sep, returning Wed, 23 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Houston George Bush Intercntl. on Sat, 19 Sep, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Wed, 23 Sep, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $389, select.

Chicago.$417 per passenger.Departing Wed, 2 Dec, returning Mon, 7 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Wed, 2 Dec, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 7 Dec, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $417, select.

Chicago.$465 per passenger.Departing Mon, 11 Jan, returning Mon, 18 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Houston George Bush Intercntl. on Mon, 11 Jan, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 18 Jan, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $465, select.

Chicago.$481 per passenger.Departing Wed, 25 Nov, returning Mon, 7 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Houston George Bush Intercntl. on Wed, 25 Nov, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 7 Dec, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $481, select.

Chicago.$523 per passenger.Departing Wed, 3 Feb, returning Sun, 7 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Houston George Bush Intercntl. on Wed, 3 Feb, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 7 Feb, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $523, select.

Chicago.$608 per passenger.Departing Mon, 21 Dec, returning Tue, 5 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Houston George Bush Intercntl. on Mon, 21 Dec, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 5 Jan, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $608, select.

Chicago.$827 per passenger.Departing Sat, 13 Mar, returning Fri, 26 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Houston George Bush Intercntl. on Sat, 13 Mar, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Fri, 26 Mar, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $827, select.

Chicago.$845 per passenger.Departing Sun, 13 Jun, returning Sat, 19 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Houston George Bush Intercntl. on Sun, 13 Jun, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 19 Jun, arriving in Houston George Bush Intercntl..Price includes taxes and charges.From $845, select.

Find the cheapest month to fly from Houston George Bush Intercntl. to Chicago Midway

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

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Houston George Bush Intercntl. to Chicago Midway: Alternative routes

Compare routes from Houston George Bush Intercntl. 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	$320
Cheapest month to fly	November

Finding cheap flights from Houston George Bush Intercntl. to Chicago Midway: Frequently asked questions

How much are return flights from Houston George Bush Intercntl. to Chicago Midway?

The best price we found for a return flight from Houston George Bush Intercntl. to Chicago Midway is $320. 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.

Which airlines fly direct from Houston George Bush Intercntl. to Chicago Midway?

Currently, there are no airlines that fly direct from Houston George Bush Intercntl. to Chicago Midway. But we found flights with one or more stops from $320.

How many flights are there a week from Houston George Bush Intercntl. to Chicago Midway?

As of September 2026, there are no flights flying from Houston George Bush Intercntl. to Chicago Midway.

When is the cheapest time to fly from Houston George Bush Intercntl. to Chicago Midway?

The cheapest month to fly from Houston George Bush Intercntl. to Chicago Midway is usually November.

Which upcoming date is cheapest to fly from Houston George Bush Intercntl. 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 George Bush Intercntl. Airport to Chicago Midway Airport on Tuesday, 10 November 2026.

Can I get a direct flight from Houston George Bush Intercntl. Airport to Chicago Midway Airport?

No airlines currently offer direct flights between Houston George Bush Intercntl. Airport and Chicago Midway Airport. Most routes have one or more stops.

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 George Bush Intercntl. Airport to Chicago Midway with?

Currently, Frontier Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from Houston George Bush Intercntl. Airport (IAH) to Chicago Midway Airport (MDW): what you need to know

Hop on a direct flight from Houston George Bush Intercntl. Airport to Chicago Midway Airport and you'll be in the air for an average of 2 hours 30 minutes.
Houston and Chicago follow the same timezone, UTC-6.
Your IAH to MDW flight 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 when you're travelling internationally.
During popular months such as July, it's a good idea to get to the airport well in advance. Arrive two hours before a domestic departure and four hours ahead of international flights when you fly during a high season in general.
Travelling to Chicago (and then discovering more of the United States!) is easy with Frontier Airlines. This popular carrier has direct flights from Houston George Bush Intercntl. Airport to Chicago Midway Airport.
Frontier Airlines tops the list for bookings on this route.
Frontier Airlines is the most punctual carrier that offers IAH to MDW flights, with 70.45% of its services arriving as planned.
Think about adding a stopover when booking your ticket from Houston George Bush Intercntl. 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 are some options between IAH and MDW:
- Nashville Airport
- Kansas City International Airport
- Dallas Love Field Airport

Handy information about Houston George Bush Intercntl. Airport (IAH)

IAH is located at 16930 JFK Boulevard.
Of the departures from Houston George Bush Intercntl. Airport, 79% arrive as scheduled at their destination.
To reach Houston George Bush Intercntl. Airport from central Houston, it takes around 30 minutes if you're going by car. Of course, this depends on traffic conditions. It's approximately 40 kilometres from the airport to the city centre.
The journey on public transport takes about 1 hour 10 minutes.
Searching for a handy hotel close to IAH? If you're catching an early flight from Houston George Bush Intercntl. Airport to Chicago Midway Airport, these accommodation options will have you moments from check-in:

Arriving at Chicago Midway Airport (MDW)

The last thing you want is a lengthy journey to your hotel if you're arriving on a late Houston George Bush Intercntl. Airport to Chicago Midway Airport flight. Reserve one of these accommodation options near MDW instead:
Travel at your own pace with a Chicago Midway Airport rental car. Book your wheels from Dollar, Hertz or Budget and experience more of Chicago and beyond.
For the lowest price, book your ride from Chicago Midway Airport around four weeks before you set off.

Getting from Chicago Midway Airport (MDW) to central Chicago

The address for MDW is 5700 South Cicero.
Chicago Midway Airport is roughly 16 kilometres from the centre of Chicago. The drive time takes around 25 minutes.
It takes around 30 minutes to get there by public transport.

When to fly to Chicago Midway Airport (MDW)

The quietest month for a flight from Houston George Bush Intercntl. Airport to Chicago Midway Airport is December, while July is the most popular. Pick the ideal time to visit Chicago based on whether you prefer a more fast-paced or easygoing experience.
Before locking in your flight from Houston George Bush Intercntl. Airport to Chicago Midway Airport, think about the kind of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 16ºC to 28ºC.
If you like cooler conditions, look for a cheap ticket from IAH to MDW in January. Average temperatures are between -12ºC and 3ºC then.

Explore more of the United States

Chicago has its own special appeal, but there are so many other parts of the United States just waiting to be discovered. Around 451 kilometres south-east of Chicago, a visit to Columbus will keep your itinerary busy. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.
Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in the United States. Experience major highlights starting with Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.