What it is: Be a wine-o without having to live on the street! Head down to Union Station and try over 250 wines from around the world. If you’re so inclined – you can get all the wine education you want, or if you’re not feeling high brow, you can just drink 250 glasses of wine (not recommended). Tickets are available online!
Dates: May 3-4, 2013
Hours: Fri & Sun 7-11pm, Sat 1-5pm
Neighborhood: West Loop
Address: Union Station, Chicago, IL 60606
Cost: Tickets $50-60 per session.
Get Directions:

What it is: Old St. Pat’s World’s Largest Block Party is not only as big as it sounds, it’s also one of the most popular Chicago festivals all summer. If you’re looking for a huge party with great music and a chance to mingle and meet other young adults, then this is probably the right street fest for you. I mean, it takes over 1000 volunteers to run the event – and they don’t even get counted as guests! There’s gonna be a ton of people and a ton going on – so check it out and help support Old St. Pat’s.
What it is: Randolph Street Market Festival is not your usual Chicago street fest. Instead, the historic West Loop neighborhood brings in over 200 hand picked sellers of high quality goods like home furnishings, vintage clothing, jewelry and collectables. It’s more of a European-style, outdoor market. But, lucky for you, it’s you don’t have to fly over an ocean to enjoy this European style festival. Just head over to Washington Blvd and check it out!