Chabad in Wicker Park has the *best* synagogue advertisements and pamphlets EVER. They are so slick and funny...they seriously do an excellent job of targeting people like me. Young, jewish and no where to go for the high holidays.
Last year, attracted by the signs I saw advertising their services, I decided to check it out for the kol nidrei service. Let's just say I was beyond surprised at how orthodox the service was! They separated men and women, there was dovening, almost everything said was in hebrew. I had no idea it was going to be like that! I was expecting young, hip, and relaxed so I felt a bit uncomfortable.
All that being said, they are very welcoming and no one seemed to care that I came wearing jeans. That is always a plus in my book. I would even probably do services here again as it is convenient and simple. But, in my opinion, this isn't really the ideal place for an interfaith couple. Someone who didn't already have some understanding of what was going on and then had to sit separated from their jewish partner might be very bored/uncomfortable.