My brother earned his pilot’s license years ago, but for whatever reason (mostly distance – he lives on the east coast) I’d never flown with him. As a non-pilot I’d been itching to do a twilight flightseeing tour and thought what better companion (and pilot) for the adventure than Brendan, who turned up in Chicago for a visit last weekend.

Out on the runway at Midway

Accustomed to the tiny airports of southern Maryland, he was positively giddy upon arrival at Midway. We stepped inside Atlantic Aviation (the “nicest FBO he’s ever set foot in”) and met our instructor Gale. We were in the air shortly before 6 pm, Brendan in the left seat.

Same city, new view

We climbed out, overflying the United Center, Soldier Field, Obama’s house and Millennium Park before turning at the lake, looping up over the water and around downtown. Views were sprawling, stunning. We were bird’s eye with the skyscrapers just as the sun began to fade, resulting in some postcard-quality photos. As a native Chicagoan, I thought I’d already seen every shade of beautiful cityscape – most certainly not the case.

Brendan later told me the highlight of the evening for him was the descent into Midway, right alongside the gigantic commercial jets. Just a bit more exciting than the usual flight. (Nothing against southern Maryland, of course.)

Brendan piloting

Categories: aerial tours