I have never done it but I am sure you could but I would do st.james and lake cook road area so that you can meet driver outside of South entrance parking lot (there is re-entry)
I have never done it before i guess try if not meet them up in the main gate for them not to pay to get in
I believe you could dont see why not considering outside food an drink is allowed. By the south entrance would be a good spot to meet
I would try the employee entrance near 295-299 Ravinia Park Rd, Highland Park, IL 60035
Best way grab cooler bag and bring your own, Really! If it 's your first time you will be amazed at what people bring. Cools wagons.chairs. sandwiches would be your best bet. My suggestion last time we went we got a sorted sub sandwiches and cut them into quarters for finger like finger foods and we brought our own drinks and cooler with a blanket some chairs good time. Maybe you can put some stuff in the backpack so you know. As to answer your question I don't think they'll get through the gates. But they may even have a hard time getting up to the front gate maybe not. Enjoy
You probably can but that's probably gonna be tricky. They have a couple of restaurants on site.
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