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$63 Cheap Flights from Houston (HOU) to Chicago (CHI)

View $63 flight on Thu, Feb 18, 2027

Popular airlines from Houston William Hobby Airport (HOU) to Chicago

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    • Cheap Flights from Houston to Chicago (HOU-CHI)

    Prices were available within the past 7 days and start at $63 for one-way flights and $120 for roundtrip, for the period specified. Prices and availability are subject to change.

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    One way

    Roundtrip

    Select Frontier Airlines flight, departing Wed, Jan 27 from Houston to Chicago, returning Mon, Feb 1, priced at $120 Found 2 hours ago

    Wed, Jan 27 - Mon, Feb 1 · IAH · ORD · Roundtrip

    Select Frontier Airlines flight, departing Wed, Jan 6 from Houston to Chicago, returning Tue, Jan 12, priced at $124 Found 3 hours ago

    Wed, Jan 6 - Tue, Jan 12 · IAH · ORD · Roundtrip

    Select Frontier Airlines flight, departing Wed, Jan 27 from Houston to Chicago, returning Wed, Feb 3, priced at $125 Just found

    Wed, Jan 27 - Wed, Feb 3 · IAH · ORD · Roundtrip

    Select Frontier Airlines flight, departing Wed, Feb 3 from Houston to Chicago, returning Sat, Feb 6, priced at $130 Just found

    Wed, Feb 3 - Sat, Feb 6 · IAH · ORD · Roundtrip

    Select Frontier Airlines flight, departing Tue, Jan 12 from Houston to Chicago, returning Wed, Jan 13, priced at $134 Found 20 hours ago

    Tue, Jan 12 - Wed, Jan 13 · IAH · ORD · Roundtrip

    Select Frontier Airlines flight, departing Tue, Feb 2 from Houston to Chicago, returning Tue, Feb 9, priced at $135 Just found

    Tue, Feb 2 - Tue, Feb 9 · IAH · ORD · Roundtrip

    Select American Airlines flight, departing Sat, Dec 12 from Houston to Chicago, returning Sat, Dec 12, priced at $224 Found 8 hours ago

    Sat, Dec 12 - Sat, Dec 12 · IAH · ORD · Roundtrip

    Select Southwest Airlines flight, departing Sat, Dec 12 from Houston to Chicago, returning Tue, Dec 15, priced at $229 Found 6 hours ago

    Sat, Dec 12 - Tue, Dec 15 · HOU · MDW · Roundtrip

    Select United flight, departing Sat, Dec 12 from Houston to Chicago, returning Tue, Dec 15, priced at $229 Found 3 hours ago

    Sat, Dec 12 - Tue, Dec 15 · IAH · ORD · Roundtrip

    Select Delta flight, departing Sat, Dec 12 from Houston to Chicago, returning Sat, Dec 12, priced at $243 Found 7 hours ago

    Sat, Dec 12 - Sat, Dec 12 · HOU · ORD · Roundtrip

    Alternative airports near Chicago

    Prices were available within the past 7 days. Prices and availability are subject to change.

    Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $258

    23 min

    Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $310

    16 min

    Find the cheapest month to fly from Houston (HOU) to Chicago (CHI)

    January is typically the cheapest month to fly

    From $114 - $282 per traveler.

    View flights in January

    Insights are based on prices from searches for economy trips of 10 days or less on our sites in the last 12 months. Insights are informative only and current prices may differ.

    Book with confidence

    Houston to Chicago Flights

    The cheapest times to fly from Houston to Chicago

    On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Houston to Chicago are during the month of January. You can find some of the cheapest flights from Houston to Chicago with Expedia's search tool and vast selection of airlines.

    The best time to book a flight from Houston to Chicago

    Sunday is one of the best days to book for cheap flights from Houston to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

    How to find cheap round-trip tickets from Houston to Chicago

    Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Houston to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $63 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

    Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Houston to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

    You could also save big by booking one of Expedia's vacation packages. Bundling together your Houston to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

    *Terms apply.

    Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

    Travel information

    Origin airportHouston William Hobby Airport
    Destination airportChicago Midway Airport
    Distance937 miles away
    Airlines servingSouthwest Airlines, Delta
    Popular airlineSouthwest Airlines
    Roundtrip price$120
    Average flight time3 hours 5 mins

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    *Available to One Key members.