It’s the holy grail as new movies keep getting more expensive: Seeing a new movie before it is released, for free. And surprisingly, it’s not that difficult to find them. Something to keep in mind: Screenings are usually only one night, so you should be flexible with dates, and arrive an hour early.
Below are my links to the best sites:
Film Metro is a great site for new screenings; you should sign up for emails to find out before others do as these disappear quickly. I tend to use junk email addresses with free services so I don’t get more spam in my mailbox.
Wild About Movies is one that you can print passes off of, but you seem to have to go through many pages to get to the right page. You can also sign up for emails.
Fatwallet is great for general deals and freebies, in a forum format. It takes a bit to get through all of the postings, but I tend to start at the last page and search for “Chicago” to save time.
Gofobo is a an active Facebook page [and separate web site searchable by zip code. Nice selection along with a sign-up but looks to be worth it. [updated 9.24/11]] – but it seems to have turned to contests rather than just printable passes. I don’t know about you, but I’m not creating an embarrassing video just to see some random movie!
Hollywood Chicago is more of an entertainment site, but you can search for “movie screening” and find limited-quantity passes available, most for answering a question. There is also an email list for this site as well.
Poptimal is another entertainment site, with free movies available for writing comments. These are far more limited.
And overall, check out radio station web sites, who have many screenings, and TV stations, who sometimes do. Below is a list of them – well worth the sign-up!
10/26/10: Not sure how I forgot this one, but Time Out Chicago has screenings fairly often.
9/24/11: Another find: BuzzBo is a Facebook page with a fair number of giveaways & screenings.

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The MIx (WTMX 101.9) has their “insiders club” that offers advance movie screenings, free DVDs, occasionally advanced concert ticket purchases, and other freebees.