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Chicago is a rough and tumble kind of town. Its no New York of course, but Chicago isn’t into the imitation game either. The struggles of the city, the nature of its people, and the love of the Cubs seems to unite everyone together. While we were there, we had the extreme fortune of finding ourselves staying at an AirBnB that captured the essence of our trip, in an elegant, comical way.

Just a block or two away from the stadium, the AirBnB was located in Wriglyville. That section of Chicago can really only be described as the “Highland Park” of Chicago for us Dallasites. Very clean, lots of shopping and cute restaurants, and just outside of the main hustle and bustle of downtown. The AirBnb we were in was located on the second floor of a chic clothing store called Two Penny Blue. Just like most buildings in Chicago, it was about five times as tall as it was wide, and very narrow. The winding stairs leading up to our rooms was about as wide as a piece of standard luggage, but through a bit of huffing and puffing we managed to lift all of our crap up there for the stay.

Opening the doors was like opening the doors to Santorini. White walls, clean corners, modern styles, and absolutely gorgeous. The wooden floors were worn with obvious years of use and abuse, but it only added to the charm. The only way to accurately describe how the layout initially was felt was “Female Bachelor Pad”, if that makes sense. The space was split level, with the two bedrooms upstairs, and the common area and kitchen downstairs. The kitchen was a modern renovation, with stainless steel, high gloss cabinets, and one of those coffee makers that costs $500 at Willams Sonoma. The living area stretched long all the way to the street facing side of the road, letting the shadow of the building cast warm hues through the glass. Wire furniture, plush couches adorned with heavy faux fur and blankets, and a long coffee table (presumably for the expensive coffee maker) just oozed social activity. It was the kind of place that was intended for early birds to rise, chat about the morning paper, send off a few emails, and make a full, hearty breakfast for the day ahead.

After our day out and about, our first night was comfortable elegance. If the downstairs had whitewashed hues and themes, the upstairs was like some interior designer just went, “what if….what if everything was white?”. And it worked. The bed was white. The sheets were white. The windowsills were white. The floor was white. The curtains, the cabinets, even the drawer handles, were, you guessed it, white. It was alluring and scary all at once. It was wonderful for pictures, but Daniel said he was worried if he spilled a cup of coffee up there that they would have to repaint the whole place. I loved it.

Chicago, being the big town that it is, has about three trillion AirBnbs. It can be tiring looking through all of them. We had a lot of options to pick, and I have no questions that I picked a perfect one for our trip. It was spacious, it was inviting, it was a welcome sight for our sore feet. We rested like royalty, and with the kitchen being as large as it was, and Daniel at the helm, we ate like kings too. When we went to Wriggly Field for a game, we could walk there without being exhausted (not that public transport in Chicago couldn’t have gotten us there). But because we walked we got a glimpse at Chicago we would have never seen before, and I like to think its because of where we stayed. Daniel and I both give it ten out of ten.


If you’re interested in booking this Airbnb here’s the link.