Explore Chicago with Debra – in May

May Day, celebrated on May 1, is an ancient, Northern Hemisphere spring festival and usually a public holiday. Dances, singing, and cake are usually part of the celebrations that the day includes. So in honor of May Day, and the glorious month of May, I say ‘take a day off to sing, dance, eat cake and explore Chicago’!

I’d start with a margarita in honor of Cinco De Mayo, well, two margaritas…with the first at The Matchbox and the second at Salpicon. To feed your inner farmer, or to just eat some great food, spend a morning at best farmer’s market in the midwest. For a bit of culture, take a walk on the wild, blue side or search for ‘meaning in the modern world’. There’s plenty of adventure, food and drink to enjoy as you explore Chicago in May..


every Wednesday and Saturday 7am–1pm

South End of Lincoln Park at the intersection of Clark and Lincoln.

A feast for the palette and soul, the Green City Market is Chicago’s only truly “green” farmer’s market, with a mission to provide a marketplace that supports and promotes local, sustainable agricultural practices. Stop by the market to meet the farmers that grow the food you can purchase that day, and learn how farmers, chefs, restauranteurs and the greater Chicago community can support each other in an effort to eat healthy food. All of this fun in the gorgeous setting of Lincoln Park!


May 5, 2015

various restaurants & bars

Celebrate Cinco de Mayo with traditional dishes at a variety of the wonderful Mexican restaurants Chicago is known for;  flavorful tacos, plenty of tequila and the best margaritas in Chicago. Enjoy special offers from many of the featured restaurants and bars, and take this opportunity to try something new; a pineapple-habanero or strawberry-basil maragrita, chili and chocolate glazed salmon, or duck confit flautas. I plan to try a margarita at as many of the featured restaurants as one day allows!


May & June 2015

3133 N Halsted

Yes, they have been here forever…but have you actually seen the show? Let your imagination run wild! Remember that time when you were little and one of your imaginary friends took your hand and led you into a world that looked like yours, only brighter? The Blue Man Group combines music, technology and comedy to create a form of entertainment that defies categorization and appeals to people of all ages. Blue Man Group’s shows have been described by critics as “innovative,” “energetic” and “wildly entertaining.” But the only way to truly understand Blue Man Group’s global popularity is to see the show for yourself.


MAY 29-31 • FRI 11AM-6PM, SAT 10AM-6PM, SUN 10AM-5PM

N Michigan Ave and E Lake St

Popping up for a three-day weekend at the end of May, top-ranked art and design show Millennium Art Festival brings the art of happiness to the heart of downtown Chicago, offering an array of artwork, including paintings, ceramics, photography, and furniture, showcasing the talents of more than 110 juried artists who participate in this city-centric festival. Blending live performances, tasty treats, and interactive art-filled experiences, Millennium Art Festival infuses a creative spirit into Chicago’s urban streets.


April 17th – June 6th, 2015

The Den Theatre

An absurd, existential comedy exploring the downfalls and disappointments of life, the obstacles that hinder true happiness, and the tragedy that is our very existence…ok, perhaps a bit heavy for a lovely day in May but a bit of self-exploration can be a good thing…the story of the Prozorov sisters, whose daily lives in a drab provincial town pale in comparison to their imagined futures in the big city. Director Geoff Button follows the gradually building devastation that results from the sisters’ comic missteps.


Friday, May 29th from 5-10pm

Saturday & Sunday, May 30th & 31st from 12-10pm

Division Street from Damen to Leavitt

In its 9th year, this signature event combines all the best elements of a great Chicago street fest; a rousing, live music bill, local independent retailers and artisans, and exciting family fun. The 2015 Fest also features a ‘Do Fashion’ area. Eat, drink, shop and explore Wicker Park; there’s something here to appeal to everyone!