Two weeks ago, my friend Jamie and I went to Chicago on a whim. We booked a last minute flight to see the bean and eat some classic Chicago Style Deep Dish Pizza. We didn’t know much about Chicago other than what we heard from friends and family but we discovered the flavor of the city while getting lost in it.
It might sound a little crazy. Who books a last minute flight just because they want pizza? Two hungry girls thats who. Don’t worry-we didn’t only eat deep dish. Our food loving travels have allowed me to write a two day eating guide that will bring you around to some of the best restaurants Chicago has to offer. I’m betting you’ll be booking your flight by the end of this post.
We landed on a sunny Tuesday morning in O’Hare Airport and scrambled to decide what we wanted for breakfast. Once we landed at the hotel, we hopped on the train and headed to the “Brooklyn” of Chicago, a hipster and charming neighborhood outside of the city known as Wicker Park. A friend of Jamie’s recommended we try Dove’s Luncheonette, a 41- stool restaurant. This Chicago hotspot has a 60’s vibe and serves up Tex-Mex flavors all day long from breakfast through dinner. We decided on sharing the Almond Oatmeal and Gazpacho de Frutas. Our mouths were watering as our steaming breakfast plates were placed in front of us. After we dug in, we knew our trip would be worth every bite. The almond oatmeal was heavenly (I don’t use that term often). I would have licked the bowl clean I could have. I moved onto the Gazpacho and was slightly disappointed. I decided to try something new, Gooseberries which is in the topping, and found I wasn’t a fan of their flavor. When served raw, like in this Gazpacho dish, Gooseberries can seem sour. Although the yogurt served with the Gazpacho was delicious, I went back for more oatmeal.
One we were done at Dove’s, we wandered across the street to Stan’s Donut Shop since Jamie and I can’t go anywhere without buying a donut. I’ve never seen a donut case with more variety. Every flavor and color was represented in one display case and I had to ask for recommendations from the staff more than once. We went with the Biscoff (Cookie Butter) Pocket, a Blueberry Old Fashioned, and some coffees to pair. After a quick photoshoot we went donut crazy. I highly recommend you take a trip to Stan’s if you find yourself in Chicago. They definitely have something for everyone.
As you can imagine, we were STUFFED. It took us the rest of the day to begin to be hungry again. We spent the rest of the day walking around Chicago and checking out all the tourist attractions like the River Walk, the Magnificent Mile and The Bean(!!). We decided to go for a late lunch of Deep Dish at Lou Malnati’s Pizzeria, an iconic Chicago pizzeria. Although my heart will always belong to New York pizza (especially Umberto’s) I have to admit that I really enjoyed Chicago style. I know, I know: blasphemous. I was surprised that the pizza wasn’t a soupy and messy as I anticipated it to be. I was convinced that I would be eating this pizza with a spoon. Lou Malnati’s does it right. their signature Butter Crust kicks up the flavor of this pizza. It’s crunchy and saucy with just enough gooey cheese. Although you can’t fold it in half and eat it with one hand, I was happy with what I got.
We surprised ourselves when we were hungry for dinner. At my boss’s recommendation, we ate at Mercat a la Planxa, a tapas restaurant that packs big flavor into little dishes. The first thing I got was the Short Rib Bread, also a recommendation from my boss, and after I licked the plate clean, I looked at the menu hungry for more. Jamie and I ordered three more courses including Charred Brussels Sprouts, Bacon Wrapped Dates, and Beef & Lamb meatballs. If you’re a fan of tapas, this is one of your go to’s in Chicago. After enjoying a bottle of wine with our meal, we went in search of another great bottle at Cindy’s Rooftop Bar. With a breathtaking view of the city and Lake Michigan, Cindy’s ins the perfect place to enjoy a drink after work or after a hard day of being a tourist.
The next morning, we decided to skip breakfast and go for lunch at the Purple Pig, a Chicago icon that almost everyone told us to go to. The Purple Pig is a Michelin Star rated restaurant that focuses on “Cheese, Swine, and Wine.” I was thrilled to eat at a Michelin Star rated place that was more than affordable, to my great surprise. For under $50 a person, we enjoyed beers, Brussels Sprouts, housemade Greek Yogurt, Fresh Calamari, and Eggplant Capontata. Justin Timberlake crooned on the radio and I was in heaven with every bite. I savored every mouthful and vowed to come back to Chicago as soon as possible.
We paid the bill and decided to walk down the Miracle Mile in search of Chicago style popcorn at Garrett Popcorn- a Chicago classic since 1949. The mixture of Cheddar and Caramel popcorn may sound weird but don’t knock it until you try it. We devoured our bags before we boarded our flight and dreamed of food all the way back to New York.
It was a whirlwind two day trip but I wouldn’t have changed any minute, or calorie eaten. Chicago, I’ll definitely be back soon!