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

Chicago is one of my favorite places. It is clean, the people are friendly, and it feels like a world-class city. For travelers, there are so many places to visit and activities to do, while for residents, it’s a wonderful mix of comfortability and excitement. And for people who love food, it’s a dream. 

Alex joined me on this trip to the windy city the day after Christmas. As a food blogger, traveling means going to tens of places, taking hundreds of pictures, eating thousands of calories. Alex was so patient with everything, standing in for minutes on end so I could get a shot of him holding pizza in a blizzard (evidence below) or letting food get cold so I could figure out the right angle to photograph our bolognese. So though this ain’t no book or essay, this guide is dedicated to the guy that made this trip fucking awesome.

Because Chicago has so much to offer, one guide can’t possibly include all the best places to go. I could write a guide solely on the desserts of Chicago, or the pizza places, or the bars. But I did try to get in a little bit of everything in this guide. I’ve got award-winning cocktails, pizza slices as big as your face, and 5 different takes on brussels sprouts (sidenote: brussels are Alex’s and my favorite veggie to order at restaurants, because they can be prepared in so many delicious ways. We just had to try them all!).

Without further adieu, let’s get to it! 

DAY 1

WHERE TO STAY – THE DANA HOTEL

The Dana Hotel, Chicago

The Dana Hotel is one of the coolest hotels I’ve ever been to. It’s modern meets industrial meets Chicago charm. Its proximity to the Magnificent Mile, the premier shopping center of Chicago, makes it a treasured location.

The Dana Hotel, Chicago

The rooms are absolutely gorgeous. They’re masculine and moody, while floor to ceiling windows bring in natural light all day. And in the evening, the view sparkles from the adjacent skyscrapers of the downtown area.

BREAKFAST – FREESTYLE FOOD + DRINK

Breakfast at Freestyle Food + Drink

 After checking in, we got a quick breakfast at Freestyle Food + Drink, the restaurant on the main floor of the Dana. As hungry travelers, we ate it all up. Alex’s huevos rancheros were made with what tasted like Doritos, which was flavor insanity.

LUNCH – DOUGH BROS

Pizza at Dough Bros, Chicago

Dough Bros is a little gem tucked away from all the madness of River North. We had the good fortune of stopping by in the middle of a snowstorm so bad that Alex and I had to grip-of-death each others’ arms so as not to fall into the street.

It was, however, totally worth it.

Pizza at Dough Bros, Chicago

I know Chicago is known for its deep dish pizza, but they sure as hell know how to do thin crust, too. We were still full from breakfast, but as the first bites hit our tongues, we went wide-eyed and gapey-mouthed. This. Pizza. Rocks.

As do the sandwiches! This meatball sub was top notch.

Meatball Sub at Dough Bros, Chicago

And be sure to grab a shot of the outside brick walls. They’re totally Instagram-worthy 🙂

FIRST DINNER – FRONTIER

Chicken Lollipops at Frontier, Chicago

We headed to the West Loop for our first dinner (yes, dinner 1 of 2, because we’re like that). Frontier is an upscale casual spot with a focus on meat. Really good meat.

Baked Mac & Cheese at Frontier, Chicago

Frontier’s menu boasts beasts for anywhere from one to a hundred people. You can call ahead to reserve a whole hog, lamb, or duck. They even have a private upstairs space with its own bar to compliment that rack of lamb 🙂

Memorable dishes at Frontier include the chicken lollipops (OMG) and the baked mac and cheese. Oh, and the s’mores dessert. Hello, lovely.

S'mores dessert at Frontier, Chicago

 And when you’re done with dinner, you can enjoy a drink by the large stone fireplace in Frontier’s beer garden. And in the summer, the floor-to-ceiling windows open to the street to become a great spot for day drinking or happy hour! 

SECOND DINNER – DOLCE ITALIAN

Dolce Italian, Chicago

Walking into Dolce Italian, one immediately feels like a cool kid. The mid century modern decor, the orange color palate, and the large open room. This is a hip place.

Can I say hip? Is that, like, totally out? Well, you know what I mean.

Lobster Ravioli at Dolce Italian, Chicago

Bolognese & Brussels Sprouts at Dolce Italian, Chicago

At the same time, the simple Italian fare offsets the elegant ambiance of the room. Tables of two are in close proximity to one another, creating a sense of communality, while large semi-circular booths line the windows for larger groups wishing to share family-style small plates.

Alex and I went here on a Sunday night, when the restaurant was a great mixture of families, couples, and young professionals. Our waitress had a slight Italian accent (sign of a good Italian restaurant, I’m telling you!) and greeted us warmly.

PB & J cocktail at Dolce Italian, Chicago

Though we had eaten four other meals that day, with each dish that graced our table, our stomachs stretched a little bit more. We absolutely loved the bolognese and the lobster ravioli. Oh, and the COCKTAILS!

I think I can speak for the both of us when I say we’ve never had better cocktails in our lives. This one was a mixture of rye bourbon, a peanut butter simple syrup, and a blueberry ice cube. Seriously. Insane.

Dolce Italian, Chicago

 DAY 2

WHERE TO STAY – THE BLACKSTONE HOTEL

The Blackstone Hotel, Chicago

Located in the South Loop of Chicago, The Blackstone Hotel is one of those timeless hotels that makes you feel like royalty. From the ornate lobby to the historical details, The Blackstone is a perfect destination for a special trip to Chicago.

Our room faced out onto Millennium Park and Lake Michigan beyond it. Though in the dead of winter, the view was still incredible.

View from The Blackstone Hotel, Chicago

Our room was bright and spacious. The bathroom was awesome; a touch of modernity in an otherwise classic room. It made me want to put my makeup on in there. 

Room at The Blackstone Hotel, Chicago

For our first day, we grabbed an early breakfast in bed before heading to a late morning brunch. We got the classic eggs, bacon, and potatoes combo, and it did not disappoint.

Room service at The Blackstone Hotel, Chicago

BRUNCH – COCHON VOLANT

Cochon Volant, Chicago

Cochon Volant is my new favorite brunch spot in Chicago. It’s part French Cafe, part contemporary cocktail bar, with Moorish details.

We were lucky enough to go on a quiet morning, so Cochon’s bar manager was nice enough to talk us through the menu. I got my favorite, lox benny, while Alex went for the Le Deux Deux Deux. And what’s brunch without a waffle? We scarfed down the Monsieur Foster.

Lox Benny at Cochon Volant, Chicago

Phenom Brunch at Cochon Volant, Chicago

If the food was fantastic, the drinks were indescribably good. We got one cocktail called Death In The Clouds that didn’t even taste like alcohol. My god. Frothy and foamy like a latte, with a rich but only slightly sweet coffee base. Like, this drink is worth planning a trip to Chicago for.

Death In The Clouds at Cochon Volant, Chicago

LUNCH / ANY EXCUSE THAT YOU CAN THINK OF TO GO HERE – BOHEMIAN HOUSE

Boho House, Chicago

Bohemian House (or Boho House for short) took the cake for us in Chicago. It was technically our last meal there, and by then we were food-ed out. But walking into Boho House felt refreshing, calm, and totally our type of place. Bright blue tufted sofas sectioned off a luxurious seating area, while rich browns and reds and yellows played up the bohemian cuisine.

Boho House, Chicago

We felt like we had to go all-out here, seeing as it was our last meal before we left Chicago (but not to confuse you all, I still have a dinner spot to tell you about 🙂 ). So with the help of our incredibly knowledgeable server, we got the cauliflower salad, the open-faced schnitzel, and the pastrami beef tongue on rye.

Hubba.

Cauliflower app at Boho House, Chicago

Open-faced Schnitzel Sandwich at Boho House, Chicago

Pastrami Beef Tongue on Rye at Boho House, Chicago

This was the only restaurant the whole week in which the chef came up to greet our table. Such a simple yet important gesture that meant so much to us. It was an absolute honor to eat there, and I can’t recommend this place enough.

DINNER – CELESTE

Celeste, Chicago

What better way to end things than at a super chic cocktail and late night dinner spot?

Walking in, you feel like you are entering some secret club where you whisper a password to the doorman. But no, behind the large door is Celeste.

Drinks at Celeste, Chicago

Fellas, Celeste is like, the ideal date night spot. It’s moody and intimate, with a phenomenal cocktail menu. We went for an Old Fashioned and a Dirty Martini.

The smashed potatoes were also excellent. It was like a potato chip and a french fry had a baby. Yeee!

Smashed Potatoes at Celeste, Chicago

Shishito Peppers at Celeste, Chicago
Roasted Chicken at Celeste, Chicago

A huge thank you to all of the following locations/people for making this trip possible:

C|Louise PR
Henson Consulting
Zapwater Communications
The Dana Hotel

The Blackstone Hotel
Dough Bros
Frontier Chicago
Dolce Italian
Cochon Volant
Boho House
Celeste

11 comments

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LOVE THIS! I literally haven’t been to ANY of the places that you mentioned yet. What the heck. And I swear, I’ve been to a lot of places, haha! Cannot get over how pretty that schnitzel picture is – and everything else!

Sarah | Broma Bakery
Reply

Thank you!!!! Oh you HAVE to. And do let me know where you go! And we should also go to a place together 🙂

Reply

Chicago is definitely on my “to visit” list and even more so now that I’ve seen this post! Great photos.

Sarah | Broma Bakery
Reply

Thank you SO MUCH my dear! I so appreciate it 🙂

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Oh my gosh, I’m so embarrassed that I LIVE here and haven’t been to a single one of the places you mentioned. Geesh. For brussels, though, next time you’re in town, you MUST try the brussels and bacon dish at mEAT in boystown. You’ll never be the same.

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What an amazing trip! This is exactly how I like to travel, aka LOTS OF FOOD. I was in Chicago back in November for the BlogHer Food Conference, but didn’t hit up ANY of these. Now I know where to go next time!

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I’ve been to Chicago three times and haven’t been to any of your suggestions. I have to on my next trip. What a great recap and omg the FOOD!!

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love love love this guide! I especially want to try Boho house, but really all of them! I’ve stayed at The Dana Hotel too and I lived a few blocks away from there for a while too. It’s SO beautiful! Sounds like you had a wonderful trip. Thanks for sharing 🙂

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This was so fun! Thank you for sharing. Your photos are gorgeous! And wow, the food. The FOOD! Lobster ravioli, yes please. Pretty much anything/everything you ate, yes please!

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Next time you must try La Sirena Clandestina! Empanadas… Pisco Sours… joy 🙂

Reply

Going to Chicago to play at Uncommon Ground and I love your guide! Definitely planning to hit up several of your mentions.

http://www.steviejewel.com

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