Chicago’s famous Berghoff Restaurant hosts the annual Oktoberfest in the city. The plaza in front of the post office downtown at Adams and Dearborn becomes the site of the German-style, open-air celebration for three days in early September. Berghoff’s version of Oktoberfest is popular with the "downtown" crowd who stop by during lunch and after work to enjoy this big Oktoberfest in the middle of the city.
Visitor’s can enjoy fresh bratwurst, barbecued chicken sandwiches, corn-on-the-cob, soft pretzels, and chocolate chip cookies along with Berghoff’s private-label beers and root beers (soft drinks and water are also available).
In addition to the good food and beer, a stage is setup to showcase a variety of local musical talent. There is usually a raffle with such prizes as a car or a vacation. Raffle proceeds benefit a local charity.
If you happen to be downtown, perhaps shopping on State Street, then you may like to stop by. I do not recommend making a special trip just to attend this fest. For a classic Chicago-style Oktoberfest, you should attend the German-American Festival, usually held around the same time of year. If you do attend, try to do so in the afternoon when there is more space. The Berghoff beer is good, but this fest gets incredibly crowded in the evenings. Most of the attendees are the city’s young professionals, some still wearing ids from their "important" jobs like at the Board of Trade or Mercantile Exchange.
If you don’t want to wait in lines for beers and brats, put your name on the list to eat an authentic dinner inside the Berghoff Restaurant, one of the best in the city.
To get there take the CTA Blue Line "L" to the Jackson stop. When you walk upstairs you will be in the middle of the plaza.