I have grew up in the Oak Park area and have lived in other cities in the country.
Oak Park is located outside of the city of Chicago. Though located reasonably close to the city life of Chicago, Oak Park is actually worth a closer look for those interested in architecture and the arts. There are several areas in Oak Park that have been designated as historic districts, which are rich in Victorian "Painted Ladies," Craftsman, and prairie style homes. Its downtown area has revitalized and is attracting "urban professionals." I also think it is fair to say that there is diversity among its residents and is liberal enough to support, if not welcome people of "alternative" lifestyles. Its residents also seem to be very liberal in their views and eco-friendly, where recycling is mandatory. Oak Park is home to authors, writers and musicians as well as corporate professionals. Notable past residents of Oak Park include Ernest Hemingway and famous architect, Frank Lloyd Wright.
It takes about 26 minutes on the green line to get into the city. If using Metra train, it takes about 10-15 minutes. So, if you work in the city, or just like going to the city for recreational activities, it is reasonably accessible from Oak Park via public transportation. There are bus routes than run down major streets in Oak Park that can get you to the train stops as well.
If you are single and plan to move to Oak Park, I suggest living near the downtown Oak Park area or Oak Park Avenue (near the train), as those areas are close to the train and you would be within walking distance to bars, restaurants, shops and other entertainment. There are plenty of rentals and condos in those areas, though parking can be a pain if a spot is not included. However, there are places where you can rent a spot in a public garage.
If you have a family, Oak Park has a decent suburban family vibe. The public library system is pretty good and the main library has many activities geared for children and families. There are also several festivals that go on during the Summer that are family oriented as well. However, the school system in Oak Park is sketchy. I don't think it is terrible, but, I don't think it is fabulous either. The public high school used to be ranked in the top 5 of the state, but in the last 20 years it has fallen considerably. I have found that resources are dedicated more for students that are struggling than anything else. If you have a gifted child, the high school does offer advanced coursework and AP classes. However, if your child is "average," they might not get as much attention. There are private school options for those who prefer that route, which are pretty good.
The Oak Park government is odd. In fact my father refers to it as "the people's republic of Oak Park." There are odd laws in place like not being able to back into a public parking spot. People selling their homes are not allowed to put up for sale signs in their front yards. If you want to do anything to your home, you have to get it cleared with the village, especially if you live in a historic area. If you live in a historic area, you cannot alter the outside of your home, meaning, you cannot add onto it or change the structure (painting, routine maintenance, replacing windows are ok). For example, if your home does not have a porch, you cannot add one. However, you can do what you want to the back of your home, as long as it is not visible from the street.
Oak Park is located in Cook County, where sales tax is very high. However, Oak Park is not far from neighboring counties with lower sales tax rates. This means, if you plan to purchase that expensive appliance, you can drive about 20 minutes outside of the county and purchase it for less. Speaking of taxes, Oak Park's housing taxes are quite high. They are so high that they are always a topic of discussion amongst residents. I have seen taxes range from $6000 to $12000+ on single family homes with yards. The tax rate will depend on the size of the home and lot and the area of Oak Park the property is located. Housing prices themselves are reasonable for the area, probably to offset the tax rate!
It's not a bad place to live and I appreciated growing up in a culturally diverse area. Growing up, I frequented museums and had plenty of exposure to the performing arts. Another positive aspect is that it is not a "cookie cutter" suburban area at all. The streets are tree-lined and homes are definitely not carbon copies of each other, like many western suburbs. In fact, I find the strip malls and sprawling subdivisions and "big-box" stores of the western suburbs, rather contrived.