Randolph Street Market Festival
The indoor/outdoor fair showcases antiques and vintage collectibles from more than 200 dealers
Roof Top Bags Tournament
Teams compete for cash prizes in a baggo tourney with plenty of food and drinks.
$25 three-course dinner 5-7 p.m.
Chicago Kentucky Derby Events
The “Run for the Roses” is considered horse racing’s most prestigious event. But just because it’s in Louisville doesn’t mean we can’t celebrate here in Chicago. A number of local restaurants, bars and race tracks will be offering Kentucky Derby specials throughout the weekend (events are on May 2, unless otherwise noted). Via Ventuno
4-6 p.m.
Chef Jim Kilberg has created a special bar menu, including Benedictine tea sandwiches with ramps, deviled eggs, oyster po’ boys with remoulade and fried okra with truffled honey, all for $5 each. Pair that with a Derby-themed cocktail menu that includes Maker’s Mark mint juleps ($6), “Belle of the Ball” (peach-macerated bourbon, cognac, absinthe, muddled brown sugar, bitters, $8) and the “Old Gray Mare” (Via Ventuno’s spin on the Old Fashioned, $6). Bluegrass and Dixieland jazz will set the sounds of the soiree.
Moonshine
3-7 p.m.
Maker’s Mark and Moonshine present Down ‘n Derby. Sample special menu items like $9 hot brown sandwiches, an open-faced, hot turkey sandwich with bacon and cheese; $9 fried green tomatoes and a $14 fresh crab cake salad. Sip on mint juleps or any Maker’s Mark drink for $4 (all day). Festive attire and fancy hats are encouraged.
Stretch Run
Friday, May 1 at 9 a.m.; Saturday, May 2 at 9 a.m.
Guests can place their wagers starting on Friday and join Stretch Run for a pre-Derby Day and Ladies/Fillies Day celebration. All ladies who stop in on Friday between 4-8 p.m. will receive a complimentary rose and chocolate covered strawberry. Saturday guests will indulge in mint juleps ($6), mojitos <$4.50) and hot dog stations set up throughout the venue. Get a 2009 Kentucky Derby glass for $10. Additional food specials will be available on the main floor all day.
The Pony
1:30-5:30 p.m.; $40
Celebrate Derby Day for a good cause at The Pony’s fundraiser event, benefiting Equestrian Connection. Guests can bid on horses from local charity Equestrian Connection, while enjoying an open bar and Southern spread of traditional food. The Pony will also feature specialty cocktails such as $5 mint juleps.
Hawthorne Race Course
11 a.m.; $50 ($4 without food/drink)
In celebration of 100 years of family-owned racing, Hawthorne is hosting “Chicago’s Biggest Kentucky Derby Party,” featuring live music, an outdoor barbecue and beer fest, a charity chili cook-off, and tent lounges with dozens of high-definition flat-screen TVs so fans can watch and wager in style (gates actually open at 8 a.m., so the real fans can come and watch the first races indoors beginning at 9:15 a.m.).
David Burke’s Primehouse
Noon-6 p.m.
Watch the Derby in style at The James, David Burke’s Primehouse’s lobby bar. Complimentary appetizers from David Burke’s will be served, including firecracker duck Rolls, mini burkers and dry-aged sirloin tacos. And of course, no Kentucky Derby party is complete without the classic libations, including mint juleps and mimosas. Specialty cocktails also include a host of David Burke’s fresh spring drinks perfect for Kentucky-style toasting, such as The Kentucky Kiss ? bulleit, grapefruit and sparkling wine; and The Flowering Meadow ? lavender Bombay, lemongrass and honey.
Timothy O’Toole’s
4 p.m.
The Streeterville pub will hold two viewing parties in one evening: the Kentucky Derby race will be shown with sound on all 47 television screens, followed by the Pacquiao-Hatton fight. In addition to special mint juleps, Chef Sean O’Brien has created special menu items, like the Derby Burger (Kentucky pimento cheese and bacon served with a side, $8.99) and Kentucky Burgoo (slow-cooked stew of chicken, beef, potatoes, onions, cabbage, tomatoes, okra, butterbeans and green peppers, with a freshly baked biscuit, $10.99).
Citizen Bar
The River North bar’s popular rooftop patio opens up on Friday; what better way to celebrate than with some mint juleps ($6) and mojito pichers ($20) on Saturday? While you’re at it, try some of the new menu items, including spicy corn chowder, thin-crust pizza and several different kinds of wings and burgers.
Check out Centerstage Chicago food and drink deals!
Five great acts playing alfresco this week. 
The best hip-hop shows taking place over the next seven days. 
Hoping to find a good Mojito. 