If you do the Metra into Chicago from Woodstock, you can buy tickets on the train going, but you need to purchase return tickets when you get there, or you get charged extra. The ticket window is off to the right as you get off the train and go through the revolving doors. Olgilvie is the last stop on the train, so you ride from Woodstock to the end.
I have not used a cab in around 15 years from Olgilvie and have never used Uber or Lyft, but when I did take the cab from the Metra station to my office, it was $5.00. They wait at the Metra station; turn left as you exit the door and they sit on the side of the building. You can, however, go behind Olgilvie and use the L train at the Clinton stop; it will get you down to within walking distance of places in the Loop. My office is in the Auditorium Building at 18 South Michigan. I take the Metra from Woodstock, get on the L Green Line headed for the Loop and get off at Adams. I will kind of suggest places centering on my building (which is fabulous to see itself. Beautiful auditorium! Designed by Louis Sullivan, mentor to Frank Lloyd Wright)
My office is not too far from the Field Museum and Shedd Acquarium across Michigan Avenue on Lake Michigan.
The Art Institute is several blocks north of the Auditorium Building on Michigan. It houses Grand Wood's American Gothic. And you can visit Millennium Park near the Art Institute with its Bean sculpture. I forget the real name of that sculpture; everyone calls it the Bean. It was hand sanded to be like a mirror, so you can see yourself in it.
We have walked to Navy Pier from the L station, although it is a long walk. Lots of people like going there.
Lincoln Park Zoo is downtown north of the Art Institute, but we have not been there, so I am not sure how to tell you to get there.
The Science and Industry Museum is farther south of the Loop. You will need a cab or something to get there.
If you get on the Green Line L train going west, you can get off at the Conservatory stop and visit Garfield Park Conservatory.
Going farther west on the Green Line is Oak Park where we used to live and that has the office of Frank Lloyd Wright and many of the homes he designed. You can take a tour of these, although only the outsides of the private homes.
Brookfield Zoo is a ways. It might be easier to drive and park there.
There is a neat French market in the basement of Olgilvie that we just discovered a few weeks ago.
If you want to see a Broadway show, most of the theaters are within walking distance.
There are a lot more smaller museums, but I have not seen any of them. I know that there is a military museum near the Art Institute
You can also do a quick tour of Woodstock. It has a quaint downtown and is the location of the film, Groundhog Day. Cute bookstore, nice restaurant in the old courthouse and jail. You can even eat in what used to be the jail cells and see if they have a show you might like at the Opera House. We saw the Buckinghams there this fall
Next do the KOA is a western town, but that appeals more to kids. We took our grandkids there. Also near there is a train museum.
Have fun! Not sure where we will be at that time. We usually go to Algonac Rally
, but this year, Kevin is being treated to a Cubs game by our daughter that weekend.