Will be working on getting my IFR rating this summer but have been looking through charts and planning flights that I would like to fly soon. Not yet really working with an instructor yet so I thought that I would ask this question here. One that I am considering is KTYQ (Indianapolis Executive) to 91C. Direct would go through Chicago Class B so that is most certainly a no go. Would like to file the route as AZHUP direct HOMRC T354 MAYSE. Using AZHUP as a convenient waypoint that is almost on a direct line to HOMRC that is shortly after takeoff. Any idea as to whether this would be accepted as filed? If so, what is the likelihood of actually flying the routing? Also, I have never heard of anyone doing this, is it possible to list two routes for the same location listing one as a preferred and a secondary one? Would likely list a direct route for the preferred and one that uses more VORs and airways for the secondary.
The big thing here is that Chicago Approach does not want to talk to you if they don't have to. Whether IFR or VFR on flight following, you're going around except in rare cases. In 23 years of flying in the area, I have gotten through the Chicago B three times, and at least two if not all three were late on Sunday nights.
KELSI is the old way to get around Chicago, and it used to be that you were either going to get KELSI, SHOOF, or over the lake, period, end of story. However, Chicago not talking to anyone not departing or arriving in their area is the entire reason that the T265 GPS airway exists, so you can use it to stay on the land side and remain with Chicago Center, Rockford Approach, and Milwaukee Approach. Use however much of it you need to stay at or outside of it. In this case, if you do KTYQ MEITZ T265 START 91C, that's almost certainly the route you'll fly.
Yes, you can file direct. No, you will NOT get it... And if you wait until ATC reroutes you, you'll be flying further than you would have if you just filed around in the first place. FWIW, the MEITZ T265 START route adds just 11 miles of total distance to your trip.
Now, if you don't mind staying VFR and conditions allow it, you can also go VFR up the lakeshore past the city of Chicago, which is something I do recommend doing while we still can! It has gotten a bit more complicated in recent years, but it's not too bad. The big complication is that if MDW is landing on the 22s, don't go at a busy time of day because you'll be smack in the wake turbulence danger zone and risk getting your wings ripped off like this guy did:
http://www.kathrynsreport.com/2013/07/piper-pa-28r-200-arrow-ii-n1549x.html
If you listen to the ATIS and MDW is not landing on the 22s, and there isn't a Bears/Sox/Cubs game going on, it's as simple as staying out of airspace, though I recommend calling for flight following on 128.2 if you're coming from the south or 120.55 if you're coming from the north. I've never been denied flight following along the lakeshore. You can sneak above KGYY's D and then descend down to 2000 and follow the shore, then climb back up remaining under the B on the north side and maybe top KUGN's D as well (only 400 feet between the two though). The route to punch in is KGYY VPFTS, just don't put that in and follow it on autopilot - You need to stay over the water, so at least rubber-band your route to the Bahai Temple north of downtown (it's on the sectional).
In any case - Fly safe and have fun!
