A good source for what is playing in Chicago throughout the year is www.theatreinchicago.com. It gives extensive information on current shows, and has a large section on future openings into Fall 2015. You can find dates, performance times, reviews, videos, seating charts, maps, nearby restaurants, etc., all wrapped up in one website.
Discounted tickets to many shows are readily available at www.hottix.org and www.goldstar.com. Both sites tend not to have seats available quite this early, but sometimes they will surprise you. Goldstar is often the better deal in terms of price, partly becuase their add-on fees aren't too bad. HotTix, besides having two sites in the Chicago Loop where you can walk in and buy discounted tickets over the counter, also offers many of the tickets online. The fees may run higher however, as Ticketmaster does their processing for online purchases, and their fees can sometimes be rather stiff. The offset is that you may be able to pick your seat - Goldstar doesn't offer that option.
If you have access to a car, don't forget to check out theatre companies in the suburbs of Chicago. Writer's Theatre (WT) in Glencoe will have both of its current shows, "Doubt" and "The Diary of Anne Frank", running that weekend. "Doubt" is being performed in a church (a nice touch) just a few blocks from where "The Diary of Anne Frank" is being performed in a teeny black box space at the back of a bookstore where you will feel like you are trapped with the Frank family. WT is currently building a brand new, state of the art, theatre designed by hot architect Jeanne Gang, but it won't be open until the second play of next season. Thus the improvised locations.
Another tip would be to see what is playing at Theatre Wit and Stage 773. They are literally side by side on Belmont on the north side of Chicago. And Theatre Wit is actually something like three theatres in one building. So if they have plays up and running, you could easily see two shows in one day, and spend the break between the two at Cooper's across the street, a decent bar/restaurant (with free parking in the back if you drive there).
Timeline Theatre and Lifeline Theatre will also be in session around that time. Both are fantastic companies, and also don't require trips to the burbs.
Don't forget that the Chicago tryout of "On Your Feet", Gloria Estefan's Broadway bound show, is scheduled to be playing at the Ford Oriental Theatre that weekend. HISTORICAL NOTE: The Oriental is a converted movie palace from the golden age of movie theatres, with a wonderfully opulent interior. And it stands on the site of where the Iroquois Theatre once stood. The Iroquois Theatre fire on December 3, 1903, is still considered the deadliest theatre fire in the history of the US.
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