United and American have round-trip flights from Houston (IAH) to Chicago (ORD) for $87-$107, NONSTOP. Cheapest Flights TUE-WED+SAT from September to December. Friday flights are available here and there for only $5 more.

Southwest is matching out of Hobby (HOU) and Midway (MDW). Their price is $100 +/- $20. Round-trip. Nonstop.

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