- Megafaun, Jon Mueller, Paulina Hollers @ The Hideout
- Y-ME Race Against Breast Cancer @ Grant Park
- Mommie Dearest @ Music Box Theatre
- El Perro Del Mar/Lykke Li @ Schubas
- Clinic @ Empty Bottle
- Elizabeth Hand and Matthew Sharpe @ The Book Cellar
- Anthem Idol @ ESPN Zone
- San Diego Padres vs. Cubs @ Wrigley Field
- Liars @ Reggies
- Arianna Huffington @ Borders Michigan Ave
- Elizabeth George @ Borders State Street
- The Interiors @ The Empty Bottle
- Wild Sweet Orange @ Metro
- David G. Whiteis @ 57th Street Books
- Yo Majesty @ The Mansion
- Nuruddin Farah @ Barnes & Noble Evanston
- World Kitchen Learning Series: Perfect Picnics in the Park
- Kat Hibbard @ Transitions Bookplace
- Benefits of Locally Grown Food @ Sulzer Library
- Taste on Chicago @ UIMA
- Charles M. Payne @ 57th Street Book
- Chip Kidd @ Quimby's
- Duran Duran @ Rosemont Theater
- A Global Warning: Understanding Climate Change @ Field Museum
- Green City Market Opens @ 1750 N. Clark
- Lynne McTaggart @ Transitions Bookplace
- Anne Laughlin & Kate Sweeney @ Women & Children First
- Powell's North Reading Series
- Gourmet Wine Cellar @ Field Museum
- President of a Chiapas fair trade coffee @ Soy Organic
- Jimmie Briggs @ International House
- Cory Doctorow @ Barnes & Noble Clybourn
- Pickup @ Kilbourn Park
- Fun Run in Andersonville @ The Runner's Edge
- Broker Boxing 2008 @ The Hilton Chicago
- Chicago Children's Museum Discussion @ City Hall
- Bronze (Record Release Show) @ Empty Bottle
- Banfi Wine Dinner with ChicaGourmets
- Jeff Parker @ The Velvet Lounge
- Portfolio Show @ SAIC
- Head of Femur/The Poison Control Center @ Schubas
- The Upset Opening Night Art Show @ Co-Prosperity Sphere
- Out of the Vault: Year of Confrontation
- Robert Tanenbaum @ Barbara's Bookstore Oak Park
- Andersonville Bike to Work Week
- Chicago Moves Day @ Daley Plaza
- American Science & Surplus Annual Scratch and Dent Sale
- Flawed: New Work by Joan Hiller @ Medicine Park
- Aloft Aerial Dance @ The Aloft Loft
- Manifest
- The Hue, Kinetix, Bumpus At Kinetic Playground
- Picked Up: Episode #6 @ Neo-Futurarium
- ALT Q @ Old Town School
- Cajun Dance @ Portage Park Center for the Arts
- Buddha Birthday Celebration @ Truc Lam Temple
- Schadenfreude Rent Party @ Hideout
- Organic Plants Sale @ Kilbourn Park
- Berry Good Fun (kids' cooking class)
- American Science & Surplus Annual Scratch and Dent Sale
- Art of Chinese Tea Ceremony @ Galewood-Mont Clare Library
- Aloft Aerial Dance @ The Aloft Loft
- Chicago Style Crafters Trunk Show
- 826 PROM @ Pulaski Park Fieldhouse
- Wicker Park Gallery Tour @ Around the Coyote
- Green Festival @ Navy Pier
- Pet Pics @ Zulu
- Hip Lit @ MCA
- Green City Market @ 1750 N. Clark
- Free-improv/electroacoustic "Supergroup" performs at Lampo - 9 p.m.
- J.A. Flynn @ Women & Children First
- 7 Diamonds Trunk Show @ His Stuff
- Anniversary Celebration @ Stellar 26
- Leona Helmsley Auction @ Leslie Hindman Auctioneer
- Treasure Hunt @ The Merchandise Mart
- Writers on the Record: Aleksandar Hemon @ Lookingglass Theatre
- Consider the Cocktail @ Weegee's
- Ravenswood Manor Neighborhood Garage Sale
- Aloft Aerial Dance @ The Aloft Loft
- Legs For Literacy Run/Walk @ Lincoln Park
- American Science & Surplus Annual Scratch and Dent Sale
- Chicago Style Crafters Trunk Show Continues
- Green Festival @ Navy Pier
- Moscow Virtuosi Chamber Orchestra @ Orchestra Hall
- Gapers Block Book Club Meeting
- The Lemon Tree @ Spertus Institute
- Pete Best @ Heartland Cafe
- Steven J. Heyman @ 57th Street Books
- Chicago Area Podcasters Association Meeting
- Marda Dunsky @ Women & Children First
- Matana Roberts @ Chicago Cultural Center
- International Ride of Silence @ Daley Plaza
- Simon Winchester @ Barnes & Noble Evanston
- Local Author Night @ The Book Cellar
- Chicago Beer Society-3rd Wednesday @ Map Room
- Girls Rock! Lottery Show Benefit @ Abbey Pub
- Jim Munroe: Therefore Repent! @ Quimby's
- Nilita Vachani @ International House
- Blewt! Sings @ Trader Todd's
- Evan Fallenberg @ Barbara's Bookstore Oak Park
- Sacramento Monarchs vs. Chicago Sky @ UIC Pavillion
- Art Smart @ LUMA
- Pilcrow Lit Fest @ Fixx Coffee Bar
- Sake 101 @ Sam's Wine & Spirits
- Milan Furniture Fair Talk @ DWR Evanston
- Jeff Parker @ The Velvet Lounge
- Troll 2 @ Music Box Theatre
- Camp Chicago
- Nahid Rachlin @ Women & Children First
- Blood On The Wall @ Empty Bottle
- Aloft Aerial Dance @ The Aloft Loft
- John Huss Moderate Combo @ Elastic Arts
- The Dollar Store Show and Pilcrow Lit Fest @ The Hideout
- Burning Ring of Truth: A Tribute to Johnny Cash @ Ronny's
- Aloft Aerial Dance @ The Aloft Loft
- Pilcrow Lit Fest
- 660 Curries Luncheon at Marigold with ChicaGourmets
- Bank of America Bike the Drive
- Constructor Craft Fair
- Aloft Aerial Dance @ The Aloft Loft
- Pilcrow Lit Fest
- The 3rd Annual Chicago Urban Golf Memorial Day Weekend Event
- Chicago Bandits Open Tryouts @ Judson University
- Live Through This: On Creativity and Self-Destruction @ Women & Children First
- Wine Cellar Raid @ Cafe Matou
- Sarah Levine @ Women & Children First
- Jennifer Stevenson, Gregory Frost and Nnedi Okorafor Mbachu @ The Book Cellar
- Jeff Parker @ The Velvet Lounge
- World Kitchen Learning Series: 40 Years in Greektown
- Lawrence Weinstein @ Transitions Bookplace
- Tim Joyce & Carl Kozlowski @ Women & Children First
- Christian Dior Trunk Show @ Saks
- Tre Femme Reception @ Palette and Chisel Academy of Fine Art
- Gapers Block 5th Anniversary Party
- Do-Division Street Fest & Sidewalk Sale
- Indie Arts Market @ Schuba's
- Do-Division Street Fest & Sidewalk Sale
- Gucci Trunk Show @ Saks
- Veggie Bike & Dine Registration Opens
- AIWF Pinot in the Park II
- Akris Trunk Show @ Saks
- Chicago Beer Society @ Goose Island
- World Kitchen Learning Series: Dining Mediterranean Style
- The Chicago Summer Wine Festival
- Mohemian Writer's Retreat
- Square Foot Exhibition At Galaxie
- AREA #6: City As Lab - Release Party
- Take Steps for Crohn's and Colitis @ Soldier Field
- World Kitchen Learning Series: The Armenian Church Ladies
