Houston to Chicago 🤠🐻 and vice versa at $157 RT

Premium Deal Alert: 13 June 2025

H-Town, meet the Windy City (and vice versa).

You'll find a million things to do in Chicago, from a stroll though this crazy awesome greenhouse to dinner and a show at Al Capone's favorite jazz joint. And while my northeastern upbringing won't let me compliment Chicago-style "pizza," I can confirm that the hot dogs there are to die for.

As for Houston, you'll probably want to start at the space center—for good reason! But if you start to feel overwhelmed by Space City's many landmarks, you can find plenty of peaceful relaxation there too. Oh, and never ever skip dinner there, because Houston BBQ is a once-in-a-lifetime experience :-)

Taking off

Routes

Round trips from Chicago (ORD):

Houston (IAH) - $157

Round trips from Houston (IAH):

Chicago (ORD) - $157

Details

Travel Dates

August-November

Airline

American, United, Southwest

Standard Fare

$250+ (non-stop)

Bags & Fees

Carry-on is included w/ American & Southwest and comes with an upgrade to "Economy" at $70 RT w/ United. Checked bag is $80 RT.

Book by

At least a few days.

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Finding trips

Step

1. We recommend Google Flights to find these trips because it has an easy-to-use calendar tool to browse dates and fares. See an example itinerary by pressing the blue button below.

Select one of the date boxes to expand the calendar view and see fares for each departure date. The fares shown will update if you pick a longer or shorter trip - trying different lengths can reveal more options.

Once you find dates at the price we listed, get a link to book directly with the airline by selecting the outbound and return flights.

Find on Google Flights