Pilot Report: Chicago Skyline Tour

by Ryan Dembroski

The alarm sounded.  It was 5:00 am. Still in bed, I groggily opened up ForeFlight on my iPhone and pulled up the weather for Milwaukee Timmerman Field (MWC). The forecast was generally favorable for VFR flight, but I kept zeroing in on one number – it was -6° Fahrenheit. That’s cold. Stupid cold.

Soon, I was bundled up and off to the airport. Today I would be flying from Timmerman down the Lake Michigan lakeshore, past the Chicago skyline (under O’Hare’s Class Bravo airspace), inland over Midway International Airport (MDW), and landing at the world famous Clow International Airport (1C5) in Bolingbrook, Illinois for breakfast. I’m not too pilot enough to say that I was a little nervous about the whole thing. I’m a relatively new private pilot who “grew up” happily buzzing around the cornfields of Wisconsin in a J-3 Cub. I would never climb into a Cub at -6°F and I had never flown below Class Bravo airspace before. For me, this was a whole new ball game.

Luckily, I wasn’t going to be doing it alone. As I pulled up to the airport, a few other sleepy pilots were wandering into Gran-Aire, Inc., the fixed base operator at Timmerman that hosted the first meeting of what was to become the Experimental Aircraft Association (EAA) on January 26, 1953. Eight months later, EAA held its first annual fly-in convention, also at Timmerman.

I would join seven other aircraft on this adventure. The local flight school was hosting a fly-out for MWC pilots and had put together a sample flight plan for us to follow. Luckier still, I had invited a fellow pilot friend, Brad, to sit right seat. A second set of eyes in the cockpit can never hurt in complicated airspace.

We gathered for a briefing and walked through the weather and procedures. Departure out of MWC wouldn’t be an issue, but there would be a moderately stiff and nearly direct crosswind at Clow. There would also be excellent pancakes. Briefing over, we all scrambled to preflight our birds.

I am now a partner in a Cessna 172 Skyhawk. She is of mid-90s vintage, but she’s got tons of gizmos and glass. She even has an upgraded engine. She goes considerably faster than 80 mph (that’s Piper Cub cruising speed in a dive). Some of my 13 partners call her “Michelle,” but to me she’s just “7MA.” She is honestly more airplane than I need, but the price is right and my partners are pretty cool dudes.

As pilot-in-command, I handed a shovel to Brad as we entered the hangar and directed him to clear the few inches of snow that were outside the door. How’s that for crew resource management?  Brad made short work of it though, and soon my preflight was complete. We stowed our bright red engine cover in the baggage compartment and opened the hangar door. Lastly, but certainly not least, we unplugged the engine preheater.  I was concerned about 7MA not being able to start. Yes, the engine was toasty due to the preheat, but… stupid cold, remember? As we pulled her out of the hangar, it seemed to me that time was critical; every second that passed without the engine running would mean tendrils of bitter cold were seeping into 7MA’s engine block.

“Man… I really hope she starts,” I thought to myself aloud.

“Me too,” Brad said. He, too, was anxious to get going and to get some cabin heat started. I couldn’t really blame him.

I turned the key and 7MA didn’t disappoint; she started right up like she always does. I kept the RPMs low so she could finish warming up gently. Minutes later, as we taxied to 22R over some patchy snow, the last of our fly-out wingmen took to the sky. Checklist complete, we barreled down the runway and chased after them, the cold thick air bolstering 7MA’s performance. “Safe flight,” our controller called out. “We’ll see you guys this afternoon.”

Flying south to Chicago from Milwaukee is actually pretty simple from a navigational point of view. You just keep the blue stuff on your left and the green stuff (or in this case, the white stuff) on your right. The challenge comes in managing all of the airspace transitions and the ever-decreasing Class Bravo shelves.

Heading east from MWC, the smooth air and now warming cabin helped build my confidence. Milwaukee  Approach sent us up to 4,500 feet and gave us a squawk code. Brad punched it in while I turned us south towards Chicago. Flying past Milwaukee’s downtown was a real treat by itself. It was nearly 8:30 am now, but the city was still waking up – as if the cold had forced everyone to stay under their Saturday morning covers. Now, up above the smoke stacks and the iconic Hoan Bridge, I was glad that I didn’t make the same decision.

Staying out over the shoreline would keep us out of Kenosha’s (ENW) airspace, but once we were abeam that field, we contacted Waukegan (UGN) whose airspace sticks out over the lake. We also began the first of our series of descents. Just south of Waukegan is where O’Hare’s upside-down wedding cake begins. It’s also the beginning of a VFR flyway. You can download FAA VFR flyway planning charts in most flight planning apps, or find them on the back of certain printed Terminal Area Charts. They provide recommended VFR routes for many complex or busy areas of airspace.

We followed the chart as we proceeded south, careful to match the well-marked navigational landmarks with the recommended altitudes along the way. The most critical time was near the Bahai Temple; wander much more than a mile inland, and you’re busting airspace. We kept ourselves out over the water, but only a little bit, as I didn’t want an ice bath if I lost the engine.

Approaching Navy Pier at 2,000 feet, the true privilege of flight was apparent. Chicago didn’t seem awake quite yet either. It sat there, below us, still and monolithic. 7MA was humming away happily. Brad pulled out his phone for a few mandatory shots. The mountainous Willis Tower (formerly the Sears Tower)  rose up high into the sky. It suddenly dawned on me that there were probably people in the tower watching our little plane fly below them. Unreal.

It seemed like we weren’t supposed to be there, practically in arms reach of it all. Some pilots preach about the freedom, and trust me when I say we are blessed. They say that aviation is the perfect metaphor for what this country stands for. I have always felt extremely lucky to be able to fly, but that assertion seemed a bit grandiose for me. But not anymore! This was exactly where we were supposed to be.

“We are now almost over Navy Pier, ready to call Midway Approach?”Brad brought me back to the task at hand. The most difficult part of the flight was coming up, and if Midway declined our transition, we would have to fly nearly to Gary, Indiana to bypass the airspace. We had the fuel to do it, but I was hungry.

I hit the transmit switch. Midway just had seven aircraft rapidly request VFR transitions over their field. I made number eight, but it didn’t matter. They cleared us to fly directly over the field.

One tip for making this trip over Chicago: the controllers often use local Chicago landmarks as navigational aids. For instance, on our return trip, they asked us to fly “just north of the Stephenson Expressway” to keep us clear of airline traffic. It helps to have a road map handy in this situation. If you aren’t familiar, don’t hesitate to ask. The folks at Midway were extremely helpful.

A few minutes later, something caught my eye low and to our left as we began to over-fly Midway. It was a Southwest 737 on short final. As we made our final turn towards Bolingbrook, the heavy jet touched down and rolled out beneath us. Crazy, but beautiful to watch.

We continued the remaining 18 nm low over the Chicago suburbs. Once we had the field in sight, Midway had a special request for us.“7MA, squawk VFR and frequency change approved…Have a great breakfast. Would you mind bringing us some pancakes on your way back?” I told them I would see what I could do.

Entering the pattern over Bolingbrook, it was easy to see why this was such a popular airport. They claim over 70,000 landings and takeoffs each year. That’s enough to make it one of the busiest general aviation airports in Illinois. Illinois pilots also know it as the home of the infamous Cavalcade of Planes show (this year happening June 6-7, 2015).

Bolingbrook reminds me of many of the approachable, community-driven airfields in Wisconsin. The only difference here is that your approach brings you over homes and businesses, instead of cows and corn. As forecast, we encountered that moderate crosswind on final for 36. Weirdly, after two years of flying, lining up on final at an airport in Chicago seemed almost…normal. The entire trip had proved far easier than expected.

Despite the crosswind, we made a decent landing. We parked next to the Milwaukee squadron and hopped outside. It was above zero now, but the cold still hit us hard. We quickly bundled up 7MA and headed inside to find other Milwaukee pilots already warming up over coffee.

We were told to expect a considerable wait at Charlie’s Restaurant (open daily from 7:00 am to 3:00 pm), but I think the frigid temps that day kept most pilots at home. That was okay with me. The pancakes were, as promised, fantastic!

EDITOR’S NOTE: By day, Ryan Dembroski is a mild mannered executive producer at a documentary film production company. By night (and on most weekends), he is a tailwheel-endorsed private pilot with a passion for sharing aviation with everyone. He is currently a partner in a C-172R based out of Milwaukee Timmerman Airport. One of Dembroski’s most enjoyable assignments was directing a documentary about the historic J-3 Piper Cub migration to Oshkosh in 2012 that involved 75 aircraft (www.cubs2oshfilm.com).

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