Halberstam attended University of Illinois, where he had been granted admission to the actor training program. Shortly after graduation in 1986 he moved to Chicago where he was immediately drawn to classics, working almost exclusively on the works of William Shakespeare. He went on to join The Stratford Festival's Young Company in Ontario and spent two years performing in a number of plays including Timon of Athens, The Knight of the Burning Pestle (title role), Much Ado About Nothing, As You Like It, and Macbeth.
In 1992, Halberstam (Artistic Director) and Marilyn Campbell (Artistic Associate) founded Writers Theatre, now in its 25th Season. It has evolved into a sophisticated two-venue organization with award-winning productions, more than 7,000 subscribers and a $6.1 million operating budget.
In its history, Writers Theatre has offered more than 100 productions, including 23 world premieres. As a direct result of the consistent artistic quality of the work, the company has been recognized with numerous awards and accolades: 118 Joseph Jefferson Award nominations, including four nods for Best Production; nine Joseph Jefferson Awards and 12 After Dark Awards, as well as numerous citations to Halberstam for excellence and contributions to the field.
At Writers Theatre, Halberstam has directed Private Lives, Look Back in Anger, Candida, Fallen Angels, The Father, Rough Crossing, Crime and Punishment, Benefactors, The Doctor's Dilemma, The Seagull, The Duchess of Malfi, Othello, Rosencrantz and Guildenstern Are Dead, She Loves Me, The Real Thing, Hamlet, Sweet Charity, Days Like Today, Isaac's Eye, and Arcadia. Michael has also co-directed "Death of a Streetcar Named Virginia Woolf: A Parody" with Stuart Carden and Julius Caesar with Scott Parkinson. He also appeared as an actor in the Writers Theatre productions of Richard II and Misalliance.
In 2005 Halberstam asked composer Joshua Schmidt to compose incidental music for a production of George Bernard Shaw's Candida he was directing at the time. Halberstam was inspired by Schmidt's compositions to commission a full musical adaptation of the play. The composer was soon joined by lyricist Jan Tranen and bookwriter Austin Pendleton, who both subtly added to and reworked Shaw's immaculately conceived text. A Minister's Wife was the result of all four individuals' dedicated collaboration and premiered at Writers Theatre in May 2009 under Halberstam's direction and designed by Brian Sidney Bembridge.
Following its success at Writers Theatre, the new musical was brought to New York City, where Halberstam once again directed the show as part of Lincoln Center Theater's 2010/11 Season and San Jose Repertory Theatre's 2012/13 season.
He has directed the operas Francesca da Ramini with the Chicago Symphony Orchestra The Rape of Lucretia with the Chicago Opera Theater, and Le Freyschutz in its North American premiere at the Ravinia Festival.
He has received awards from The Chicago Drama League, The Arts & Business Council, and the Chicago Lawyers for the Creative Arts. He received the 2010 Zelda Fichandler Award from the Stage Directors and Choreographers Society, which recognizes an outstanding director or choreographer who is transforming the regional arts land scape through singular creativity and artistry in theatre. In 2013 he received the Artistic Achievement Award from the League of Chicago Theatres and was named "Chicagoan of the Year" for Theater by the Chicago Tribune. In 2016 he received an Award of Honor from the Illinois Theatre Association.