Does that route offer any options at all to glide to an emergency landing from 1500 when the engine quits? Ditching in Lake Michigan with fixed gear doesn't sound like a tempting option.
I fly the shoreline quite often, flying at 1700. There are few places within gliding distance -- excluding the water itself. As others have mentioned, now that the weather is improving, those places become populated. That's good news and bad news. The bad news is you can't land where there are a lot of people. The good news is there will be a dozen 911 calls alerting responders to your location. There are also a few stretches of Lake Shore Drive where you can land, especially south of downtown.
An Ercoupe landed safely on LSD last year, after Oshkosh.
Some beaches are less busy than others. Loyola Beach, for example, doesn't get crowded on weekdays. North Avenue beach is busy all the time. Hollywood beach is another promising place that may be less crowded. There is green space south of it where you can also land. From Foster Beach to Montrose Beach, the frontage road called N. Simonds Dr. may be an option. On the weekends, however, it is packed with cars parked at-angle on both curbsides. Montrose Beach is another option but on weekends it's a very popular place for dog guardians because it's the only dog beach in the city.
From Montrose Harbor to downtown, your only option is the Lake Shore Drive. Then you get Northerly Island (former site of Meigs Field) and South Lake Shore Drive. The south parking lot at Soldier's Field is an option but not the stadium itself: there is never a touchdown here
. That flat roof of the convention center (Arie Crown Theater) may look tempting but it's questionable if it can take the impact. (The roof collapsed in 1967 after a fire, and it was rebuilt). The lakeside green space south of the convention center is usually less crowded compared to the north, so that may be an option. As you are coming abeam Hyde Park (marked "Hotels" on the Chicago TAC), your best option if you can make it is the Midway Plaisance, the green corridor that splits the University of Chicago campus and runs east/west. That will also place you within 1/2 mile of the best trauma center in the region. The Jackson Park Golf Course south of Jackson Harbor may be your last option. At this point, you will be turning on course and climbing for your enroute segment.
Last week I tried a new approach to downtown Chicago that offered more spectacular views. I followed the shoreline to the south, turned west over Monroe harbor, and then flew north back to join the shoreline and to continue south to Hyde Park. The views, as you loop around downtown, are incredible and at 1700 you're at the 67th floor of Sears (Willis) Tower. But for about 3 miles there is no viable place for an emergency landing other than a bendy river crossed by many, many bridges. Anyway,
here's a brief video from that loop around the Loop (notice the typo indicating that Goose Island is to the left when, in fact, it's to the right).
The places above are my "landing zones", as I have thought about my options quite a bit. Their names are identifiable on Google Maps. I like flying the route, I know my passengers enjoy it, and I feel that I have a few options for a survivable landing.
Couple more suggestions: (1) plan your route around the TAC's landmarks, e.g., shoreline from "BAHAI TEMPLE" to "HOTELS". (2) As others have recommended, call for flight following. If you approach from the north, you'll probably get on 120.55. Abeam O'Hare, you'll be handed off probably to 128.2 who will stay with you for the most part. They are very helpful. And so are the controllers at KUGN.
The shoreline route is not as congested as I thought it 'd be. On weekdays, I have not not received more than 4-5 VFR traffic advisories. On weekends, maybe 8-10 for the entire route from BAHAI down to the CRIB. Usually, I get more advisories about 737s when Midway lands to the southwest or northwest.
Overall it's a memorable flight and with a bit of preparation, a safe one too.
