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Southwest® flights from Houston (Hobby) to Chicago (Midway) from $85

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Low fares from Houston (Hobby) to Chicago (Midway)

$

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 08/18/2026

One-way

Basic

From
$85
Seen: 20 hrs ago

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 07/28/2026

One-way

Basic

From
$85
Seen: 4 hrs ago

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 07/22/2026

One-way

Basic

From
$85
Seen: 3 hrs ago

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 06/16/2026

One-way

Basic

From
$85
Seen: 2 hrs ago

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 07/21/2026

One-way

Basic

From
$85
Seen: 19 hrs ago

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 07/07/2026

One-way

Basic

From
$85
Seen: 6 hrs ago

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Explore flights from Houston (Hobby) to Chicago (Midway)

May 2026
From$146*
Seen: 10 hrs ago
One Way/Basic
Jun 2026
From$85*
Seen: 6 hrs ago
One Way/Basic
Jul 2026
From$85*
Seen: 7 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $85
cmp-daily-histogram-bars-legend-max-price-aria-label $335
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    • Range$85-$335

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    William P. Hobby Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 24 minutes
    Distance:
    937 miles

    Route Information

    156† Weekly flights
    • 5‡ Nonstop flights per day Monday through Friday
    • 5‡ Nonstop flights on Saturday
    • 5‡ Nonstop flights on Sunday

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Houston to Chicago Flight Duration, Distance, and Route Details

    Here’s what you should expect on your flight from Houston, TX to Chicago, IL:

    • Average flight time: Just under 2.5 hours
    • Approximate distance: ~1,400 miles
    • Time zone change: None

    Getting From Midway to Chicago and Nearby Areas

    Chicago Midway International Airport (MDW) is the smaller, more chilled-out sister airport of O'Hare, and it's conveniently located just 10 miles from downtown Chicago. Here are a few ways to get from the airport to the city:

    • The “L” train: For a fast and budget-friendly trip, you can catch the CTA Orange Line train right at the airport. Generally, it'll get you to the Loop in about 25 to 30 minutes.
    • Rideshares and taxis: Rideshares will be waiting right outside the terminal. The trip to downtown usually takes about 30 to 40 minutes, depending on traffic.
    • Rental cars: If you need your own wheels and the freedom to explore at your own pace, rental cars are just a quick shuttle ride away from the main terminal.

    How to Find Cheap Flights from Houston to Chicago

    Finding a great deal on flights from Houston to Chicago is easier than you might think. Here are a few tips to get you started:

    • Use the Low Fare Calendar: If you haven't committed to specific dates yet, check the Southwest Low Fare Calendar for our hottest deals on flights to Chicago.
    • Book early: Tickets go up in price as the day of travel approaches, so try to book your flight from Houston Hobby to Chicago as soon as you have firm travel plans.
    • Fly during off-peak times: This is a popular route for corporate travel, so you can often find lower fares on Tuesdays and Thursdays, when business travel demand is lower.
    • Sign up for fare alerts: Let the deals come to you. Sign up for email alerts to get notified about price drops and sales on flights from Houston to Chicago.

    Questions we hear the most

    The average flight time from Houston (Hobby) to Chicago (Midway) is 2 hours 24 minutes.
    There are 156 weekly flights from Houston (Hobby) to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Houston (Hobby) to Chicago (Midway) 5 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Houston (Hobby) to Chicago (Midway) 5 times per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Houston (Hobby) to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Houston (Hobby) to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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