Bridgeport

With its cool coffee shops and industrial working class vibe, Bridgeport is a great neighbourhood to visit. Nicknamed ‘Hardscrabble’, Bridgeport is historically Irish-American, full of dive bars and blue collared families. It’s still true, but things are changing as college kids flock to hang their art in Bridgeport’s many warehouse-turned-art studios. But regardless, right now you have the best of both worlds, an art scene hidden enough to still be unpretentious.

So head to Bridgeport Coffeeshop, my personal favourite in the city, for excellent vibes and a great cup of Joe. Across the street is Maria’s, a bar and savoury pie restaurant, which is not all that expensive if you’re down for a faux-British vibe. The Zhou B Art Center is an old factory turned into a fantastic art gallery, and great views of the city can be seen if you sneak onto the roof (not that I did). Speaking of views, one of the best of the Chicago skyline can be seen from Palmisano Park. For some reason I only seem to see couples there, but as far as I’m concerned it’s too good for just dates. And Third Friday Open Studios at Bridgeport is one of the most fun things I’ve done in Chicago, so check that out if you like art, artists and lots of free wine and food.