Chicago, Illinois

 

The Windy City is one of those places that everyone needs to visit at least once. Instead of suffering through a 12-hour road trip, save yourself time — and stress, and gas — by booking a 2.5-hour flight to the iconic Illinois city instead. Both American Airlines and United Airlines offer flights to Chicago O’Hare International Airport (ORD), while Southwest Airlines arrives at the slightly smaller Chicago Midway International Airport (MDW).

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