Weekend Getaway: Chicago

Many months ago, I was asked to be a bridesmaid for one of my best friends. The wedding was in Chicago, so Jeff and I booked our tickets to the Windy City primed and ready to check out the iconic sights. What we didn’t anticipate was how jet-lagged we would be for a quick trip, so our sight-seeing was not as extensive as usual. But we still walked away with some hidden foodie gems and memories from walking the streets of Chicago.

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The empty streets of Wicker Park.

Our AirBnB was in the heart of Wicker Park, the trendy and hip part of town where the bars stay open until 5am and the “L” train runs constantly. We never felt unsafe in the neighborhood, but we did become first-time uber users on this trip. It’s funny how we never thought twice about walking around the streets of the foreign cities we have visited, but when we set foot on the Chicago soil, we were more cautious.

But for some amazing food, I would definitely recommend combing Wicker Park. Tons of pubs and restaurants mean it’s a high traffic area for unique eats. Starving from our flight, we stumbled into the first place we saw called Umami Burger. It was about 4 o’clock, so it was pretty slow, but our waiter was the definition of positivity as he rattled off recommendations and what makes this place different.

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Delicious and welcomed Umami Burger in Wicker Park. A must try for burger enthusiasts and gluten-free foodies.

They have in-house homemade sauces (garlic aioli, jalapeno ranch, and habanero) and even a rockin’ homemade ketchup that come out regardless of what you order. And because I’m gluten-free, our waiter ran over the ingredients in his head to make sure I walked out happy. I ordered the Ahi Tuna Burger with no bun, and Jeff got the Truffle Burger. We shared the sweet potato fries that came with a cinnamon and brown sugar topping. The food was amazing. If you’re in the Chicago area, you must go find this place. They take care of you, and the food backs up the price.

Right across the street from Umami Burger is Jeni’s Ice Cream. With incredibly unique flavors, we were hard pressed to pick. I chose a mix of Brown Butter Almond Brittle, Salted Peanut Butter, and Torrone (toasted almonds with white chocolate, honey and sea salt). I first heard about Jeni’s on The Splendid Table Podcast, and was stunned to see it casually sitting in Wicker Park. They do have gluten-free ice cream sandwiches, but I didn’t try one of those since it seemed a bit much for a treat.

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Jeni’s in Wicker Park. Do not miss this place.

I will take a second to shout out another gelato shop: Black Dog Gelato. When we first started planning Chicago, we saw this place as a “must see” in the town. We happened to be a fifteen minute walk from the shop and made it a point to try it out. They are well-known for their funky flavors like Rosemary Irish Cream and Maple Cayenne Bacon, but they were obviously on the end of their shipment because our choices were not so exotic. Jeff enjoyed his French Toast Blueberry flavor, and I tried the Chocolate Toffee Coffee. We had waited months for funky flavors, so were a little disappointed with the selection available, but it was still delicious.

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Black Dog Gelato may be a place to try in summer. October didn’t offer many flavors.

For a breakfast place in Wicker Park, I cannot recommend Kanela Breakfast Club enough. They had a pretty extensive selection with French press coffee and gluten-free and healthy choices. Filled with fun cookbooks and trendy flair, the food was fresh and made to order, which is what you should expect for breakfast.

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A kickin’ place for amazing and healthy breakfast options in Wicker Park.

Before I mention the last place to try in the city, I will preface by saying, we eat extremely clean while at home, so we reward ourselves when we travel. If you only read our travel entries, you might think we just eat ice cream and pizza everyday. We do not.

That being said, the last place I’ll mention for amazing treats is Stan’s Donuts in Wicker Park. I have not had a donut in years. I went gluten-free in 2011 and have not looked back. So, when Stan’s Donuts offered “gluten-less” treats, my eyes turned into saucers. I tried the Pistachio Gluten-Less, and was not disappointed. Thankfully, it was on the small side, so I didn’t feel too shameful upon devouring every calorie. It was delightful.

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Yes! They had gluten-free donuts! End of the visit celebrations commenced here.

* * * * *

But we did not just eat while we were in Chicago. We did make some time to wander around downtown and take in the iconic skyline before our flight. The subway system was a piece of cake, and we got a three-day pass for $20, which made transport really easy. The Washington stop dropped us off in the middle of the metropolis and we marveled at the buildings. The first we saw was the Trump Tower. It was hard to miss since the man’s name takes up two floors worth of window space.

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The menacing Trump Tower in the heart of Chicago.

As we headed toward the mirrored Bean in Millennium Park, by way of the Chicago Theatre, we stopped in the Chicago Cultural Center.

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I walked the streets Frank Sinatra sang about!

It was a gorgeous building with an architecture exhibit happening, so we admired some mini-models and photographs of the greater Chicago area before seeing the park. The building was also home to Story Corps featured on NPR. It was fun to see the familiar on American soil.

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Inside the Chicago Cultural Center.

A game Jeff and I play here in England is when we overhear conversations out and about, we try to identify where the people are from. We are not very good at this game, but we can at least pick out the Americans. As we walked around the grounds of the park, we were thrown upon hearing the American accent. I know it’s silly, but we have been so accustomed to the English accent, the American twang caught us by surprise each and every time.

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Millennium Park was massive! And mostly empty. They were setting the stage for the Chicago Marathon, so most of the roads were blocked and there was very little foot traffic as we roamed around the Lincoln Memorial and community gardens. We didn’t have time to duck into the Art Institute of Chicago, but we do wish we could have spared a few hours in there. But before we had to get ready for the rehearsal dinner, we wanted to see Lake Michigan.

Lake Michigan is huge. Flying over it, we could have sworn it was the Atlantic Ocean, but it was a mere lake. The temperature dropped steadily with each step toward the water front, and when we finally made it to the edge, it was freezing with insane gusts of wind. We stayed just long enough to say, “Well, there it is!” before getting on the bus back to town. The water was so choppy, it was said people take the opportunity to surf. But it was still beautiful to see the sea-foam green against the cloudy blue sky.

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The last sight we got to see was the Garfield Park Conservatory where the wedding was held. The grounds are huge with several green houses surrounding a large park. As soon as we walked in, we were hit with some much needed heat from the Chicago cold. It made for a lovely venue with greenery surrounding us and gorgeous windows showcasing the pink sunset and night sky.

If you’re in Chicago, I wholly recommend taking an afternoon to walk around this beautiful conservatory, but I will caution that it is not the safest neighborhood. As we drove to the location, several gun shots went off before hearing a few police sirens. So, take a cab, car, or uber. Walking is discouraged.

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While it was a quick trip to the Windy City, we did enjoy our time there. It’s a gritty and closed-in city, for sure, but not without its monuments and history.

Jeff and I at the wedding having a wonderful time. We make a handsome couple.

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