From DBQ?

Tip: Sit on the left side for takeoff.

Passengers will see the lush, rolling hills of the Driftless Area and the expansive Mississippi River valley as the aircraft climbs away from the airport.

DBQ → ORD

Dubuque IA to Chicago

While both sides offer views of the Mississippi River and Illinois prairies, the right side is preferred for the iconic view of the Chicago skyline on final approach to O'Hare.

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Most Scenic Flight Routes from DBQ | Airside Views