American Airlines and United have round-trip flights from Houston (IAH) to Chicago or Miami (ORD/MIA) for $75, NONSTOP. Flights November to April. Weekends available. Origin/Destination reversible.
Dates around Christmas and New Years are currently available.
Change fees are waived and carry-on bag is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
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Click for more details and booking links Nonstop Flights: Houston to/from Chicago or Miami $75 r/t [November-April + Christmas/NYE] – American Airlines / United