Royal Jordanian has round-trip flights from Chicago (ORD) to Dubai (DXB) for $539 with a connection. Flights in November, January, February, and March. No Thursday departures. Extended weekends available.
Note: Some small OTAs on Skyscanner have this for $514. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour “free” period. Use unknown booking sites at your own risk.
Click for more details and booking links Cheap Flights: Chicago to Dubai $514-$539 r/t [Nov, Jan, Feb, Mar] – Royal Jordanian