Cheap Flight Tickets from Houston (HOU) to Chicago (MDW), Starting at $237

Good to Know: Cheapest and Fastest HOU - MDW Flights

Useful information for finding best airline tickets from William P Hobby to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$334

WN Southwest Airlines • nonstop • 3h 45m

Jan 09 – Jan 13

The cheapest round trip flight from Houston to Chicago (HOU-MDW-HOU) is currently $334

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Cheapest Direct Flight

$334

WN Southwest Airlines • nonstop • 3h 45m

Jan 09

The cheapest nonstop flight from Houston to Chicago (HOU-MDW) is currently $334

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Fastest Flight

3h 40m

The fastest nonstop flight from Houston to Chicago (HOU-MDW) takes 3h 40m

Top Airlines Flying from Houston to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

Latest Flight Deals from Houston (HOU) to Chicago (MDW)

Compare and book low fare round-trip air tickets from Houston to Chicago. Ideal for travelers with confirmed return itineraries.

Jan 09 - Jan 13, Economy
WN
Houston → Chicago
3h 45m
7:00 AM - 9:25 AM • nonstop
WN
Houston → Chicago
4h 5m
8:05 PM - 10:50 PM • nonstop
$334
Southwest Airlines
Jan 12 - Jan 12, Economy
WN
Houston → Chicago
3h 45m
2:10 PM - 4:35 PM • nonstop
WN
Houston → Chicago
19h 5m
9:00 PM - 8:45 AM • 1 stop
$344
Southwest Airlines
Jan 11 - Jan 13, Economy
WN
Houston → Chicago
7h 35m
11:30 AM - 4:25 PM • 1 stop
WN
Houston → Chicago
4h 5m
4:40 PM - 7:25 PM • nonstop
$344
Southwest Airlines
Jan 11 - Jan 13, Economy
WN
Houston → Chicago
3h 40m
9:50 AM - 12:10 PM • nonstop
WN
Houston → Chicago
7h 25m
12:25 PM - 5:10 PM • 1 stop
$344
Southwest Airlines
Jan 12 - Jan 12, Economy
WN
Houston → Chicago
15h 5m
5:40 AM - 2:45 PM • 2 stops
WN
Houston → Chicago
4h 5m
8:05 PM - 10:50 PM • nonstop
$349
Southwest Airlines
Jan 12 - Jan 12, Economy
WN
Houston → Chicago
16h 50m
6:20 AM - 4:30 PM • 2 stops
WN
Houston → Chicago
19h 5m
9:00 PM - 8:45 AM • 1 stop
$359
Southwest Airlines

Fly from Houston to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Houston to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Houston to Chicago Flights

What are the airports in Houston?
HOU
What’s the most popular airline flying from HOU to MDW?
The most popular airline flying from Houston to Chicago are
Can I fly from HOU to MDW non-stop?
Yes, you can fly HOU to MDW non-stop on
Which airlines fly nonstop between Houston and Chicago?
The non-stop flights between Houston and Chicago are .
What’s the earliest departure time from HOU to MDW Airport?
The earliest flight leaves HOU at 5:00 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Houston to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from HOU to MDW?
Read the fare rules of the Houston to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Houston and Chicago?
operate flights between Houston and Chicago
How long does a flight from Houston to Chicago take?
It takes approximately 2 hour to fly non-stop from HOU to MDW, which is 936.96 miles by air.
Which airlines provide the cheapest flights from Houston (HOU) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from HOU were found on WN : USD 344
Do I need a passport to fly between HOU and MDW?
No
What’s the latest departure time from HOU to MDW ?
The last flight leaves HOU at 8:20 pm

Houston (HOU) to Chicago (MDW): Airport Information

Origin Airport William P Hobby , Houston, US
Destination Airport Chicago Midway International , Chicago, US
Distance 937 miles

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