Haute Top 5: How to Celebrate MDW In Chicago

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Memorial Day Weekend marks the unofficial start to summer and all that is good about the city of Chicago. Here are five haute ways to fete the occasion this year.

1 Randolph Street Market

This European-style, indoor-outdoor mega-market has been called "the Barney's of Vintage" for good reason: it regularly features more than 200 vendors offering everything from furnishings and art, to vintage clothing, jewelry, collectibles, and more. Memorial Day Weekend marks the market's Summer Season Grand Opener: expect a garden party theme, a vinyl-swap meet, a fancy food festival and a global goods bazaar in addition to regularly scheduled shopping nirvana.

2 ROOF on the WIT JetSet Series Kickoff

ROOF on the WIT's summer Jet Set series makes its return this year with three weekend-long themed parties inspired by exotic locales. First up is MDW's Barcelona-inspired event on Friday, May 26 and Saturday, May 27. Besides a view from the 27th story bar, the WIT promises Spanish dishes like chicken and chorizo paella and Spanish fried egg, plus cocktails like the Spanish Mistress, made with rum, chili peppers and passionfruit.
201 N. State St.

3 Greektown Mediterranean Wine Festival

Grapes and gyros, galore. The inaugural Greektown Mediterranean Wine Festival takes place May 27-28, promising fun for oenophiles and foodies alike. Dishes will be served up by the area's top restaurants, and daily afternoon wine tastings (from 2:00 – 9:00 p.m.) allow ticket holders to sample up to 15 varietals with the purchase of a $40 tasting pass.
Halsted St. between Van Buren and Jackson.

4 Detroit Tigers & Boston Red Sox at Chicago White Sox

The White Sox are home all MDW long. The Sox kick off the weekend with a straight double-header against the Detroit Lions on Friday night, followed by day games on Saturday and Sunday. Monday starts a new series against eponymous rival the Boston Red Sox. Can't decided which game to attend? With ticket prices starting around $10, you won't have to choose.
Guaranteed Rate Field, 333 W. 35th St.

5 Get Out on the Water

They say the only better thing than owning a boat is having a friend who does. And if you don't happen to have one of those available next weekend, no need to kiss your plans of fresh-water fishing or partying in the playpen goodbye. Instead, try one of Chicago's now-plentiful boat rental services, like Boatbound (sort of like an AirBnB for boats) to lock up a day spent on the open water.