Houston to Chicago 
and vice versa at $157 RT
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 ✈️
Tip Published: Jun 13, 2025
Round trips from Chicago (ORD):
- Houston (IAH) - $157
Round trips from Houston (IAH):
- Chicago (ORD) - $157
How to Book
This is a Premium deal for Jack's Flight Club members only. For step by step instructions on how to book it you'll need to login or upgrade to Premium membership.