48 Hours In Chicago {A Foodie’s Guide To The City}

The city’s diverse culture, history and architecture are expressed in its food. The art of Italian pizza making is a tradition dating back to the 1800s that has been passed down from generation to generation. Chicago boasts several other world-class cuisines like Mexican and Indian cuisine which share some interesting parallels with their respective cultures.

48 Hours In Chicago is a foodie’s guide to the city. The best 3 days in chicago are the first, third, and fifth weekends of the month.

Chicago is one of my favorite cities in the United States. It is clean, the people are kind, and it has the appearance of a world-class metropolis. There are several places to explore and things to participate in for visitors, while residents enjoy a fantastic blend of comfort and excitement. It’s also a dream come true for foodies. 

The day after Christmas, Alex accompanied me on my excursion to the Windy City. Traveling as a food blogger entails visiting dozens of locations, shooting hundreds of photographs, and consuming thousands of calories. Alex was very patient with everything, standing in for minutes on end so I could capture a picture of him holding pizza in a snowstorm (proof below) or for food to cool so I could shoot our bolognese from the perfect perspective. This guide is dedicated to the man who made this trip fucking fantastic, despite the fact that it isn’t a book or an essay.

Because Chicago has so much to offer, it’s impossible to cover all of the top locations to visit in one guide. I could create a guide purely on Chicago’s sweets, pizza joints, and bars. However, in this tutorial, I tried to provide a little bit of everything. I’ve got award-winning drinks, pizza pieces the size of your head, and five different ways to eat brussels sprouts (sidenote: brussels sprouts are Alex’s and mine favorite vegetable to order at restaurants since they can be served in so many different ways). We had no choice but to try them all!).

Let’s get started without further ado! 

DAY 1

THE DANA HOTEL IS A GOOD PLACE TO STAY.

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One of the nicest hotels I’ve ever visited is the Dana Hotel. It’s a mix of contemporary and industrial with a dash of Chicago flair. Its closeness to Chicago’s Magnificent Mile, the city’s top retail district, making it a prized site.

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The rooms are just breathtaking. They’re dark and brooding, with floor-to-ceiling windows that let in plenty of natural light throughout the day. The view from the nearby buildings of the downtown area glows in the evening.

DRINK + BREAKFAST – FREESTYLE FOOD

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 We had a short breakfast at Freestyle Food + Drink, the Dana’s main floor restaurant, after checking in. We devoured it all like hungry tourists. Alex’s huevos rancheros had a flavor that tasted like Doritos, which was insane.

DOUGH BROS LUNCH

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Dough Bros is a hidden treasure in the midst of River North’s chaos. We had the good fortune of coming by during a particularly terrible snowfall, and Alex and I had to clutch each other’s arms to keep from falling into the street.

It was, nevertheless, well worth the effort.

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I understand that Chicago is famed for its deep dish pizza, but they also know how to make thin crust. We were still full from breakfast, but as soon as the first bits struck our tongues, our eyes widened and our mouths gaped. This. Pizza. Is. AWESOME.

Likewise, the sandwiches! This meatball sub was incredible.

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Also, don’t forget to take a picture of the brick walls on the exterior. They’re perfect for Instagram.

FRONTIER – FIRST DINNER

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We went to the West Loop for our first meal (yep, the first of two; we’re that way). Frontier is an upmarket casual restaurant that specializes on meat. Meat of exceptional quality.

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Frontier’s menu includes monsters for groups of one to a hundred. You may book a whole hog, lamb, or duck by calling ahead. To go with that rack of lamb, they even offer a private upstairs room with its own bar.

The chicken lollipops (OMG) and the baked mac & cheese are two of Frontier’s most memorable meals. Oh, and don’t forget about the s’mores dessert. Good day, nice.

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 After dinner, relax with a drink in Frontier’s beer garden, which has a massive stone fireplace. The floor-to-ceiling windows open to the street in the summer, making it a wonderful setting for day drinking or happy hour! 

DOLCE ITALIAN FOR THE SECOND DINNER

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When you go into Dolce Italian, you instantly feel like a hip kid. The huge open area, the mid-century modern décor, and the orange color palette. This is a trendy spot.

Is it OK to use the word “hip”? Is it completely out of the question? You know what I’m talking about.

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At the same time, the room’s sophisticated environment is balanced by the modest Italian meal. Large semi-circular booths flank the windows for bigger parties looking to share family-style small meals, while tables of two are near to one another, providing a feeling of communality.

On a Sunday night, Alex and I went here, and the restaurant was packed with families, couples, and young professionals. Our server had a tiny Italian accent and welcomed us cordially (sign of a fantastic Italian restaurant, I’m telling you!).

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Our tummies extended a little more with each dish that graced our table, despite the fact that we had already eaten four meals that day. The bolognese and lobster ravioli were both delicious. Oh, and don’t forget about the COCKTAILS!

I believe I can speak for both of us when I say that we have never had finer drinks. A rye bourbon cocktail with a peanut butter simple syrup and a blueberry ice cube. Seriously. Insane.

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 DAY 2

THE BLACKSTONE HOTEL IS THE PLACE TO STAY.

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The Blackstone Hotel, located in Chicago’s South Loop, is one of those classic hotels that makes you feel like royalty. The Blackstone is a fantastic place for a memorable vacation to Chicago, from the beautiful lobby to the historical elements.

Our accommodation had a view of Millennium Park and, beyond it, Lake Michigan. Even though it was the dead of winter, the vista was breathtaking.

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Our room was light and airy, with enough of space. The bathroom was fantastic; it added a contemporary twist to an already traditional area. It inspired me to put on my makeup in there. 

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We had an early breakfast in bed on our first day before travelling to a late morning lunch. We had the traditional eggs, bacon, and potatoes, which did not disappoint.

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COCHON VOLANT BRUNCH

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My new favorite brunch place in Chicago is Cochon Volant. It’s a mix of a French cafe and a modern cocktail bar with Moorish touches.

We went on a quiet morning, so the bartender at Cochon was kind enough to walk us through the menu. Alex ordered the Le Deux Deux Deux, while I ordered my favorite, the lox benny. Brunch isn’t complete without a waffle, after all. Monsieur Foster was devoured by us.

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If the meal was amazing, the beverages were out of this world. Death In The Clouds was a beverage that didn’t even taste like alcohol. Oh, my gosh. Like a latte, it’s frothy and foaming, with a rich but not too sweet coffee base. This cocktail, for example, is worth arranging a trip to Chicago for.

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GO HERE FOR LUNCH OR ANY OTHER EXCUSE YOU CAN THINK OF – BOHEMIAN HOUSE

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For us in Chicago, Bohemian House (or Boho House for short) stole the cake. It was officially our final lunch there, and we were quite stuffed. Walking inside Boho House, on the other hand, felt refreshing, quiet, and just what we were looking for. Rich browns, reds, and yellows played up the boho food, while bright blue tufted couches separated a posh sitting area.

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We felt obligated to go all out here since it was our last lunch before leaving Chicago (but don’t worry, I still have a supper location to recommend). We ordered the cauliflower salad, open-faced schnitzel, and pastrami beef tongue on rye with the guidance of our wonderfully informed waitress.

Hubba.

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This was the only restaurant throughout the whole week where the chef came over to our table to welcome us. It was such a little yet meaningful gesture that meant so lot to us. It was a true privilege to dine there, and I cannot recommend this restaurant highly enough.

CELESTE FOR DINNER

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What better way to round off the evening than with a classy drink and late-night dinner?

When you go in, you get the impression that you’re entering a private club where you have to speak a password to the doorman. But no, Celeste is waiting for you inside the huge door.

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Celeste, Fellas, is the ultimate date night place. It’s dark and cozy, with a fantastic cocktail list. An Old Fashioned and a Dirty Martini were our drinks of choice.

Smashed potatoes were also delicious. It was like a cross between a potato chip and a french fry. Yeee!

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Thank you very much to the following places and individuals that helped make our trip possible:

C|Louise PR Henson Consulting C|Louise PR Henson Consulting C|Louise PR Hen Zapwater Communications is a company that specializes in public relations. The Dana Hotel is located in Dana Point, California. Dough Bros Frontier Chicago Dolce Italian Cochon Volant Boho House Celeste The Blackstone Hotel Dough Bros Frontier Chicago Dolce Italian Cochon Volant Boho House

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The “chicago blogger guide” is a blog that gives the reader a look at what Chicago has to offer. This includes food, bars and restaurants, shopping, and more.

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