Growing up about 30 miles north of Chicago, my friends and I frequently commuted downtown to be tourists in our own city as soon as we were old enough to take the train by ourselves. Many of our trips involved trying new restaurants, cafes, bakeries, or markets, and over winter break this year, I made it my goal to revisit this tradition. With a clean palette and a little help from my friends, I tried menu items at places in Chicago I had never heard of but also stopped by some of my old favorites for a new treat or meal. Here are 8 of Chicago’s best old and new dining spots that you should try if you ever find yourself in the heart of the Midwest.
1. Christkindlmarket
For the past 23 years, the Christkindlmarket has stood from mid-November to December 24th in the heart of Chicago in honor of a traditional German Christmas. Christkindlmarket represents a tradition that originated in 16th century Nuremberg, Germany. At the market, rows of tents are lined up featuring vendors selling an array of warm snacks. One of Christkindlmarket’s more popular attractions is its hot chocolate served in clay mugs that customers get to bring home. When my friends and I stopped by for the first time a couple days before Christmas, we witnessed the hot chocolate line stretch around the entire market. Rather than waiting too long, we ended up trying some caramel corn and admired the German traditions that help bring the Christmas spirit to the chilly Chicago streets.
2. Magnolia Bakery
You may already be familiar with Magnolia Bakery, since it has locations across the country from Los Angeles to Boston and numerous cities in between including DC. The New York-based bakery may be best known for its famous banana pudding, but offers other sweet treats from a wide range of cakes to freshly baked cookies. If you stop by in the early hours, you can try their assortment of breakfast selections, including muffins and scones. Peet’s Coffee & Tea is also served at Magnolia’s, a perfect pair with any breakfast or dessert. The ambiance in the bakery is very tranquil and welcoming, with soft pastel colors making up the decor and covering the walls. When we stopped by Magnolia Bakery after shopping at Block 37, a shopping center in Chicago’s Loop neighborhood, I tried a rich and mouth-watering cream cheese brownie – which was gone within seconds.
3. Hub 51
Located at 51 W Hubbard Street, Hub 51 is a trendy brunch, lunch and dinner spot with a wide variety of options on the menu. From seafood to burgers to tacos, Hub 51 seems to have something for even the pickiest of eaters. I was surprised to find that although each of my friends ordered something completely different, each dish was so good that it tasted like Hub 51 specialized in only this type of cuisine. I ordered a hummus and pita plate and a crunchy tuna roll with tempura rice. My friends who eat meat tried cheeseburgers, steak, short ribs or BBQ chicken, while a couple of my vegan friends at the table could choose from an array of salads.
4. Firecakes Donuts
Just around the corner from Hub 51 stands a tiny shop called Firecakes, serving a variety of Chicago’s best homemade donuts. Since the quaint little store only has room for a counter and a delicious display of donuts, customers can take their selection to go or enjoy outdoor seating when the weather is nice. Beyond just donuts, Firecakes is also known for their espresso drinks and tea. Although Firecakes offers extravagant dessert options including Mardi Gras themed king cake donuts and donut ice cream sandwiches, I always stick to the classic old-fashioned glazed and can easily say that it is the best donut I have yet to try anywhere.
5. Hoosier Mama Pie Company
Hoosier Mama is a must for any and all dessert lovers. It’s somewhere that I visited frequently throughout high school, as it has not only great desserts but an array of coffee, sandwiches and salads. But they are best known for their 50+ variety of pies. My all time favorite is the sugar pie à la mode. It’s not hard to tell just how popular the pie shop is at seemingly all hours – I’ve been there for everything from an early morning coffee, a midday sandwich and a late night slice of pie, and it seems that nearly every table is always full. The vibrant cafe is constantly buzzing with busy college students, 20-somethings catching up over coffee, or visitors who read some of the many high reviews for Hoosier Mama online.
6. Cupitol Coffee & Eatery
With multiple locations throughout the Chicago area, Cupitol aims to create a lounge style atmosphere with elements of a restaurant, cafe and bakery. Their drink menu covers just about any type of espresso or freshly squeezed juice you can imagine, along with full menus for breakfast, lunch and dinner. The spacious cafe has comfy couches and chairs for visitors to sit back and enjoy their coffee in a homemade mug. When my friend and I went, we enjoyed the warm and inviting atmosphere so much that we sat back to catch up until they told us they were closing. Similar to Hoosier Mama, customers stop by steadily throughout the day and business never seems to be slow. This comes as no surprise – Cupitol has it all, and is pushing the boundaries of what a cafe can become.
7. Big.Fat.Cookie.
You can find some of the most delicious and gooiest dough you’ll ever try in your life at Big.Fat.Cookie. The cookies come out of the oven weighing a whopping six ounces, so they can be shared among a few people, or devoured in one sitting. Known for their large Instagram following and posts that will make your mouth water, my friends and I had never actually tried one in real life but only saw their pictures on social media. Big.Fat.Cookie. does not have their own store, but instead they sell their cookies at local establishments such as Cafe Corbel, Lakeview Kitchen & Market, and Nonnia Cafe. We stopped by Cafe Corbel and got to choose from an array of selections such as triple chocolate, Oreo, s’mores, many variations of peanut butter, Nutella, and more. We split a few different ones (my personal favorite was classic chocolate chip) and found them to be just as delicious as they appeared in the pictures.
8. Bar Siena/Bombobar
Bar Siena stands in the center of Chicago’s West Loop, a formerly industrial neighborhood that is quickly transforming into an area for new, up and coming restaurants. The two-story brick restaurant is best known for their Italian food with both a casual sports bar and more upscale dining options upstairs. Attached to Bar Siena is Bombobar, a walk-up dessert stand that has gained attention on social media in the past few years for its picturesque Italian bombolinis and bomobolatos. A.K.A. hole-less donuts with a cream filling in the middle as well as ice cream sandwiches dipped in various toppings. Rather than going to the walk-up shop, diners at Bar Siena can order from Bomobar’s menu to have their dessert brought straight to the table.
Whether you stop by one, two or all of these spots, your next trip to Chicago is guaranteed to be a sweet one!