Does it matter which Airport I fly into to go to the Hilton on South Michigan Avenue?

Melissa

Midway is closer to the center of Chicago.

But not by much. You should choose first based on price of ticket, desirable flight times and airline preferences. All those being equal, Midway is marginally a better choice.

I recently flew into Midway and found it very easy to navigate and an easy train ride into the city.

Depending on what airline you are taking it really doesn't matter if you take public transportation. O'hare will be allot more by taxi than Midway. But the CTA L has lines that go to each airport O'hare (Blue Line) and Midway (Orange Line). I believe it is $2 now one way so that is a ton better than a cab ride. Either way is easy.

I don't think it matters much easier, but Midway is smaller and easier to navigate, and closer to downtown.

easier = either.