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Cheap Flights & Flight Ticket Price from Houston to Chicago – From ₱ 8,051.07

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Houston to Chicago

Flight Tips & Deals: Cheap Ticket Prices, Best Time to Fly, and Travel Duration (Houston to Chicago)

Cheapest one-way flight

₱ 8,051.07

Cheapest round-trip flight

Cheapest month to fly

June

Shortest flight duration

2 hr(s), 25 mins

When Is the Cheapest Month & Date to Fly from Houston to Chicago?

Houston to Chicago flight schedule today

Planning to fly soon? Check out the updated Houston to Chicago flight schedule & time for today and tomorrow. The shortest flight takes just 2 hr 25 mins. Compare departure times and airlines to find the best deal.

Sun, 1 Jun 2025

Mon, 2 Jun 2025

Tue, 3 Jun 2025

Airline	Departure Time	Arrival Time	Origin airport	Destination airport
Southwest Airlines	06:55	09:20	Houston (HOU)	Chicago (MDW)	Book flight
Southwest Airlines	09:05	11:30	Houston (HOU)	Chicago (MDW)	Book flight
Southwest Airlines	12:35	17:05	Houston (HOU)	Chicago (MDW)	Book flight
Southwest Airlines	13:55	19:20	Houston (HOU)	Chicago (MDW)	Book flight
Southwest Airlines	14:50	17:20	Houston (HOU)	Chicago (MDW)	Book flight
Southwest Airlines	16:45	21:55	Houston (HOU)	Chicago (MDW)	Book flight
Southwest Airlines	17:25	21:55	Houston (HOU)	Chicago (MDW)	Book flight
Southwest Airlines	18:20	20:45	Houston (HOU)	Chicago (MDW)	Book flight
Southwest Airlines	21:25	23:50	Houston (HOU)	Chicago (MDW)	Book flight

Which Airlines Offer Direct Flights from Houston to Chicago?

Discover airlines with direct flights from Houston to Chicago and get there in as fast as 2 hr 25 mins. Avoid layovers and book nonstop flights with trusted carriers flying this popular route.

Choose your favorite airline to fly from Houston to Chicago. With airlines flying directly, you can arrive at your Chicago in 2 hr 25 mins.

Southwest Airlines

See Airlines

About Chicago

Looking for cheap flights from Houston to Chicago? Discover the best deals for flight tickets on Traveloka! Flying from Houston to Chicago will be more enjoyable with our exclusive Traveloka flight promo. Not just flights, you can also find discounted hotels, airport transfers, and attraction tickets from all over the world. With our complete product offering, booking one-way, round-trip, and multi-city flights will be much easier. Book now and dive into endless adventures with Traveloka!

Facts About Chicago

Flight Duration	2 hr(s) 25 mins
Airport in Houston	William P Hobby (HOU)
Airport in Chicago	Chicago Midway International Airport (MDW)

Frequently Asked Questions

How much is a flight ticket from Houston to Chicago?

Planning to take off from Houston to Chicago? Grab your ticket on Traveloka with prices starting from , along with additional discounts & promos that can be found on our promo page.

How early should I get to the airport for a domestic & international flight?

For domestic flights, we recommend arriving at the airport at least 2 hours before your scheduled departure time. For international flights, aim to be at the airport at least 3 hours prior to ensure smooth check-in, security checks, and to account for any unexpected delays. It’s better to be early and relaxed than rushing at the last minute right?

When is the best time to buy airline tickets?

Timing is everything when it comes to grabbing airline tickets. Typically, it’s best to book around 4-6 weeks in advance for domestic flights and 2-3 months for international routes. But the prices also depend on the travel demand, seasonality, and major events. You can always monitor the fare trends on Traveloka and set alerts to catch the best deals or promotions!

What is the cheapest day to fly to Chicago?

Looking for the best deals to Chicago? Historically, midweek flights (particularly on Tuesdays and Wednesdays), tend to be cheaper due to lower demand. However, airfares can fluctuate so we recommend keeping an eye on flight prices and being flexible with your travel dates. Booking in advance can be one the hacks to travel to Chicago without breaking the bank!

What information do I need to know when booking a flight?

When booking a flight, every choice sets the tone for your trip. From the preferred flight route – be it direct or with layovers – to the in-flight experience – whether you opt for a standard economy seat or a luxurious first-class journey – and understanding baggage limits, there's a lot to weigh. Other considerations include travel insurance and the airline's booking policies.

How far in advance should I book an international flight?

For international flights, it’s wise to start your search about 5-6 months ahead with the optimal booking window being around 3-4 months before departure. This period often provides a balance between good fares and a reasonable choice of flight times and routes. But please note that several factors such as destination popularity, peak travel season, and regional major events can influence the timeline.

Do I need a passport and visa to fly between Houston to Chicago?

Traveling from Houston to Chicago typically requires specific documents. For international flights, a passport is almost always necessary. However, for domestic flights, neither a passport nor a visa is usually required, but an official ID will be needed. The necessity of a visa depends on the traveler's citizenship and Chicago's entry regulations. It's crucial to verify visa requirements, as rules can differ between countries.

Why should I book my flight with Traveloka?

Booking flight tickets with Traveloka can feel like diving into an ocean of options! Our platform provides the most comprehensive choices to ensure you find the perfect flight for your adventure. With our smooth booking process, you'll also be provided with a variety of payment methods. Anxious about transacting online? We've got you covered with our top-tier security for each transaction! With Traveloka, your flight booking journey becomes hassle-free!

How long does it take to fly from Houston to Chicago?

2 hour(s) and 25 minutes is the shortest flight time from Houston to Chicago.