Macys Glamorama takes center stage on Aug. 9, traditionally one of the biggest annual fashion extravaganzes in the city. Sheryl Crow is the star performer this year, along with Cirque du Soleil. This year's show and after party takes place at the Harris Theatre, and showcases looks by designers such as Jean Paul Gualtier, Tommy Hilfiger and more. Tickets start at $75 for show only.
The always-festive Northalsted Market Days will be held Aug. 10-11. More than 100,000 people from across the country will converge on Halsted Street between Belmont and Addison for what's billed as the largest two-day street fair in the Midwest. Entertainment includes Wilson Philips and 10,000 Maniacs. $8 suggested donation
Hit Navy Pier Aug. 7-11 for the Chicago Match Cup and Tall Ships extravaganza. Watch the races, part of the Alpari World Match Racing Tour, or check out the Tall Ships which are available for Dockside Boarding, viewing and Sail Away Cruises.
The Bud Billiken Parade steps off at 10 am on Aug. 10 on King Drive at Oakwood Blvd. The historic parade serves as the unofficial call for back to school.
There's still a few weeks left to party on the beach. Hit North Avenue Beach Aug. 10 for The Big Dig, a volleyball tournament topped off with a performance by Coolio. If volleyball isn't your thing, there's also bags and dodgeball tournaments, along with a limbo contest. $15
Head over to the Roscoe Village neighborhood for Retro on Roscoe, August 10-11. Enjoy three stages of entertainment and six blocks of food vendors and area merchants. 12-10 p.m. each day, $10 Suggested Donation.
Taste of the Nation hits the Navy Pier Grand Ballroom on Aug. 14 at 7 p.m. This event usually sells out, and features nearly 100 chefs and mixologists joining together with the goal of ending childhood hunger. Tickets $125
Step Up Women's Network presents its third annual Shine & Dine event on Aug. 15 at 6 pm at the River East Art Center. Sample food and cocktails from various Chicago restaurants with all proceeds benefiting charitable programs empowering teen girls in the Chicago area. Tickets $115