Cheap Flight Tickets from Houston (HOU) to Chicago (MDW), Starting at $404

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

$508

WN Southwest Airlines • 1 stop • 20h 20m

Nov 01 – Nov 06

The cheapest round trip flight from Houston to Chicago (HOU-MDW-HOU) is currently $508

🔍 Search Flights

Cheapest Direct Flight

$404

AA American Airlines • nonstop • 4h 17m

Nov 01

The cheapest nonstop flight from Houston to Chicago (HOU-MDW) is currently $404

🔍 Search Flights

Fastest Flight

3h 45m

The fastest nonstop flight from Houston to Chicago (HOU-MDW) takes 3h 45m

Top Airlines Flying from Houston to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

American Airlines, AA

American 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.

Nov 01 - Nov 06, Economy
WN
Houston → Chicago
20h 20m
8:25 PM - 8:45 AM • 1 stop
WN
Houston → Chicago
3h 55m
12:25 PM - 3:00 PM • nonstop
$508
Southwest Airlines
Nov 01 - Nov 06, Economy
WN
Houston → Chicago
3h 45m
10:40 PM - 1:05 AM • nonstop
WN
Houston → Chicago
4h
5:20 PM - 8:00 PM • nonstop
$633
Southwest Airlines
Nov 01 - Nov 06, Economy
WN
Houston → Chicago
3h 50m
7:50 AM - 10:20 AM • nonstop
WN
Houston → Chicago
4h 10m
9:20 PM - 12:10 AM • nonstop
$633
Southwest Airlines
Nov 01 - Nov 06, Economy
WN
Houston → Chicago
3h 45m
5:50 PM - 8:15 PM • nonstop
WN
Houston → Chicago
6h 50m
4:50 PM - 9:00 PM • 1 stop
$638
Southwest Airlines
Nov 01 - Nov 06, Economy
WN
Houston → Chicago
3h 45m
9:40 AM - 12:05 PM • nonstop
WN
Houston → Chicago
6h 50m
4:50 PM - 9:00 PM • 1 stop
$638
Southwest Airlines
Nov 01 - Nov 06, Economy
WN
Houston → Chicago
6h 40m
8:00 AM - 12:00 PM • 1 stop
WN
Houston → Chicago
3h 55m
12:25 PM - 3:00 PM • nonstop
$638
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 7:50 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 638
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 10:40 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

More Flight Options for Houston (HOU) and Chicago (MDW)

Why Fareleaders for HOU to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Houston to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on HOU to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Houston to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Houston (HOU) to Chicago (MDW)
Terms and Conditions*