Southwest® flights from Houston Hobby to Chicago-Midway from $106

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.