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!
WHERE TO STAY – THE DANA HOTEL
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 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
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
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.
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.
And be sure to grab a shot of the outside brick walls. They’re totally Instagram-worthy 🙂
FIRST DINNER – FRONTIER
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.
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.
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
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.
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.
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.
WHERE TO STAY – THE BLACKSTONE HOTEL
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.
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.
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.
BRUNCH – COCHON VOLANT
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.
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.
LUNCH / ANY EXCUSE THAT YOU CAN THINK OF TO GO HERE – BOHEMIAN HOUSE
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.
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.
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
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.
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!
A huge thank you to all of the following locations/people for making this trip possible: