In terms of rail service, I would have the entire train announcement system redone (in terms of the logic that governs when what announcements are played). The system should be more of a point to point routing system where a train driver selects a route such as O'Hare to Forest Park, then can select any station to start and any station to end, as long as the start station is behind the end station in the given direction. Drivers operating trains that terminate at UIC/Racine/Jeff Park/Rosemont would still select this route, except that instead of selecting O'Hare and Forest Park as their start and end stations (or vice versa). As for the lines that terminate in the Loop, they would have a continuous route that would go Kimball to Kimball via the Outer Loop for the Brown Line, etc. As for buses, I would add the capability to program Pace, and O'Hare bus routes, for use when Pace and/or O'Hare would require to use CTA's Buses if they were short for some reason (weather, demand beyond the highest of predictions). CTA should also have a system of shuttle bus route numbers, so as to differentiate different shuttle buses serving the same stations. All of the shuttle bus route numbers would be prefixed with a S (examples: S1, S2, S3...). CTA would have some tool on their computers where they could define shuttle bus routes and put times when they go into and out of service. An example is when CTA decides to operate a shuttle bus covering Green Line service between Roosevelt and 35th-Bronzeville-IIT station, they would insert it into the route number that they would like and set it to take effect for that route number 1 hour before, up until 30 minutes after the service is supposed to finish. If they put the aforementioned example with the Green Line into the S1 route and then decided that the next weekend they would have a Blue Line shuttle between Rosemont and Harlem, then the bus drivers would always select S1 for both weekends, providing that they were operating a Green Line shuttle for the first weekend and a Blue line shuttle for the second weekend. The files would tell the bus which stops that the bus replaces on which lines, where the boarding location is, whether the stop is for boarding passengers, exiting passengers or both and what fare to charge (whether to charge a premium O'Hare fare, the normal CTA fare, or a fare representative of a Metra Zone). Stops would be announced as normal, with slightly more information due to the higher amount of space between 'L' stations when compared with bus stops. (such as "Lawrence and Rockwell for Rockwell Brown Line"). Bus routes providing express service to replace a section of track (such as running shuttle buses between O'Hare and Jefferson Park express when the section between O'Hare and Rosemont is closed for signal work) would be prefixed with SX (examples: SX1, SX2) and would have the same operating procedures and tools the S routes.
For the actual trains that are actually run, I would expand Red Line service to have equal frequencies in both directions, instead of having more service southbound in the morning and northbound during the evening. I would extend the small number of Blue Line trains that start at 54th/Cermak depot to be in service between 54th/Cermak and Jefferson Park, and possibly O'Hare. For the Brown Line, I would add Mimble/Kidway (Midway -> Kimball/Kimball -> Midway) service to evening peak. For the Green Line, I would add a reversing siding to the north of Garfield or an additional platform to operate shuttle services between Ashland/63rd / Cottage Grove and Garfield in order to have equal service on the entirety of the Green Line. The Orange Line would get owl service, running between Roosevelt and Midway via all intermediate stations (passengers can change at Roosevelt for Red Line or buses for the loop). For the Purple Line, I would bring back the Purple Line Express Saturday service and Redo their announcements:
Train: "This is a Purple Line Express."
Me in my head: "...to where?" (knowing that some passengers could be confused of where the train is actually going)
For the Yellow Line, I would merge all of the Yellow Line trains with Purple Line trains to have an Skokie/Linden express service during times when Purple Line express service is operating. The Purple Line trains would always be in front and would stop at the 8 car marks at all stations at and south of Howard. The Yellow Line train would connect to the back of the Purple Line trains and the Yellow Line drivers would then step off and wait for their next train (either from the depot or from the Loop) to take up the Skokie Branch. Due to the higher presence of trains on the Purple Line when compared to the Yellow Line, all Rush period Yellow Line Trains would go to the Loop (except those towards the very beginning or end of the rush period where Purple Line trains are less frequent than the Yellow Line trains) and most Purple Line trains would go to the Loop (including all trains towards the start/end of the rush periods due to the difference in frequency of Purple and Yellow Line trains). Purple Line trains who merge with the Yellow Line trains will run as 8 car trains and will split again at Howard, with the Purple Line portion leaving first and always being the front 6 cars. Purple Line trains who don't merge with any Yellow Line train will run as they currently do (stopping at all 6 car stopping marks). This would occur at all times that both the Yellow Line and Purple Line Express are operating.
For New Years Eve/New Years Day service, I would have increased service on all CTA rail lines (lines with lightest loads would get every 20 minute service, medium load lines would get ever 15 minute service, heavy load lines would get ever 10 minute service during the later part and would get 15, 10 and 7.5 (alternating 7-8 minutes) respectively during the earlier part. Purple Line express would operate, with all Purple line trains going to the Loop via the express. At around 4-5 am, train service would start to ease into the normal service. Purple Line Express service would start easing out by going to 1/2 of trains going to the Loop, then 1/3 and then no service at all, which would happen around 7-8 am (possibly earlier depending on usage). Metra lines would run all services that run on Sundays at hourly intervals (with select lines increased to half-hourly service) and all services that don't run on Sundays having service every 90 minutes (1.5 hours). Pace and CTA should operate limited service on most of their weekday only/Monday to Saturday bus routes, including express buses, which would run in both directions during the night. Some routes would not receive service as their route is covered by a series of other routes.
For Metra trains, I would start the electrification process, where by a certain time, all Metra lines would be electrified. New rolling stock would be ordered with destination signs to indicate where the train goes and which stations it stops at. I would also have Metra accept Ventra. At larger stations like Union station or OTC, barriers or turnstiles would be installed. Each turnstile/barrier would have 1 Ventra reader, 1-3 ticket slots on the front, 1-3 ticket slots at the top and a scanner to read mobile tickets. Larger stations that serve Metra only would have one ticket slot on the front, where the ticket would be inserted and one ticket slot on the top where the ticket would be collected from. The machine would read the ticket and ensure that it is valid for the zone that the station in question is in. Stations that serve Metra and either South Shore Line OR Amtrak would have a second slot for the other operator's tickets and it would work in the same way, only ensuring that the ticket in question is valid at the station in question based on this operator's fare structure. If any station serves Metra, Amtrak and South Shore Line, then the turnstiles at this station would have three slots, one for each operator, working all working in the same way. The Metra ticket slot would always be on the top, the South Shore Line one would be second to top and the Amtrak one would always be on the bottom. Ventra tickets would not be accepted at Metra stations, but contactless PAYG, Apple Pay/Samsung Pay/Google Pay (or whatever smartphone payment systems are available for use on Ventra) PAYG, and Ventra cards would be accepted. Ventra cards would be required to have at least four dollars on them (or two dollars if the card is an RTA reduce fare permit or student Ventra Card). If the user traveled through more zones than their card has sufficient funds for, they would be permitted to exit, but would incur an negative balance and would not be permitted to travel until they refilled their card to the required minimum. All turnstiles would require the user to insert or scan their ticket or tap their PAYG card/smartphone or Ventra card on entry and exit to charge the correct fare and ensure that the ticket is valid for all zones travelled. At quieter stations, a Ventra reader would be installed, with Ventra/PAYG users expected to touch in and out on it whenever they enter or leave the station. If the system is unable to determine where the passenger has traveled, they will be charged the maximum fare (Ventra and PAYG users only). This would be either because one card entered but never exited or exited and never entered or entered one station and the exited without traveling and had stayed their for a long time (the system would think that the person made a journey to somewhere, then returned back to their start station to get a free fare). If a person enters, and then exits before a certain amount of time, then they would not be charged.
Metra should also trial an O'Hare express service once the O'Hare ATS opens, With hourly to half hourly service depending on the time of day, running Union Station to O'Hare transfer express and then returning back to Union Station express. The fare should be higher than the North Central Service fare (Zone A-D) for that journey. If it is successful, they should trial extending the service north of O'Hare to serve communities in the far northwest/north-northwest area, with select trains continuing beyond O'Hare. For these trains that continue, Passengers would be charged a higher fare, which would apply to all passengers going to O'Hare or Union station via the O'Hare express and to all passengers when North Central Service trains are operating, regardless of where they are traveling.