Printers Row Lit Fest: June 9-10. Dearborn St. south of Congress. A large book fair that features a lot of book sellers, mostly inexpensive used books, some food, talks by authors, cooking demos and a variety of other happenings.
Party at St. Mike's in Old Town: June. 1633 N. Cleveland. A well attended block party that has live music and plenty of beer. There will be a lot of 20 and 30 year olds having a fun time.
Wells Street Art Fair: June 9-10, Wells St. between Division and North. Held on the same weekend as the Old Town Art Fair and St. Mikes. The art tends to be more affordable that at Old Town. There is plenty to eat and drinks and the taverns on Wells will be packed all day.
Chicago Pride Parade: June 24, noon, Halsted and Belmont. A gay pride parade that attracts huge crowds, including many straight people. It is a spectacle for those with an open mind.
Gold Coast Art Fair: June 30- July1. An art fair that is mostly about the art. There will be some dinning option and drinks but the attendees are there to see the many top local artist. Armando Pedroso is worth seeking out.
Old St. Pat’s Church World's Largest Block Party: June 29 & 30. Madison & Des Plaines, near GreekTown. The name says it all. It is a huge party with music acts and lots of beer.
Shefffeld Garden Walk July 21-22, $7, $10 after 3:00, Webster & Sheffield. A chance to look into the garden in one of Chicago's best neighborhoods. It turns into a big party at night with lots of beer and well known music acts.
Milwaukee Avenue Arts Festival: July 20-22. On N. Milwaukee between California and Kimball. A festival featuring a wide variety of local artists. The art is often more edgy and affordable than at many of the big festivals. There is also music, dinning options and family activities.
Lollapalooza: August 3-5. Grant Park. A long running and enormous music festival that features a long list of nationally known acts. Even if you have no interest in the festival it could really disrupt your plans if you are going anywhere on the Museum Campus or to Millennium Park..
Lakeview East Festival of the Arts: Sept 8 & 9. On Broadway north of Belmont. Over 150 local artists will be featured. It is one of the more laid back art festivals.
Chicago Gourmet: Sept. 29-30. Millennium Park. Over 100 chefs will be serving up the latest creations. Many of Chicago's celebrity chefs will be there. The list includes Ted Allen, Rick Bayless, Gale Gand and Stephanie Izard.