TRAVEL – Chicago in Four Days (with little to no sleep)

When we travel to a new city, we hit it hard. Forget about coming home relaxed and rejuvenated, we’re there to experience what the city has to offer, less so as tourists, but more like a local would. We do the deep dive, 20,000 steps a day, 2,000 photos and a handful of new Facebook friends by the time we return home.

Chicago has been a bucket list destination for us for a long time, but with no business travel to the city, and no personal contacts to push us to visit, it remained on the list – a big mistake! Home to 2.7 million people, Chicago is America’s 3rd largest city. It was recently named "City of the Year" by GayCities.com and the Boyztown community was named "best gay neighbourhood in the world" by Out Traveler Magazine.

If this wasn’t enough to draw us in, we also learned that the week we were available to go was Pride - one of America’s largest – so the stars felt aligned.

Leaving on a Thursday from Calgary, the flight is a super easy three hours, and with only a one-hour time difference, visiting The Windy City for a long weekend is a breeze. The bigger problem here was deciding what we could endeavor to see and do, where to eat, drink, take in Pride activities, and not come home in tandem body bags. Clearly, we needed the help of some Chicagoans to point us in the right direction, and fortunately they were all willing to help.

You’ll find that the people of Chicago are proud of their city! Friendly, funny, and open, it’s not difficult to make a real connection with a local. We were fortunate enough to meet a group of guys on day one at Navy Pier Pride ("Queer the Pier" they were calling it). We found the event online and were drawn to promise of the headliner that evening – CeCe Peniston. At first, we were a little bit underwhelmed by the small crowd of the event, discovering it more of a family event - and given the distance between it and Boyztown it made sense - but we soon discovered that we were in exactly the right place.

CeCe was a delight! She got the crowd bouncing, she was funny, and her voice could have filled a stadium. The mixed, unpretentious crowd danced in the square and towards the end of her set we enjoyed fireworks overhead. Our new friends, a crew of Mexican-American Chicago locals quickly took us under their wings...