Like most Chicagoans, I am infinitely proud of the city I called home for so long. I always get incredibly excited when I have the opportunity to share my favourite city in the world with others. Chicago has a plethora to offer visitors including stunning architecture, world-class museums, an endless amount of sporting events, a dreamy live music scene, and in my humble opinion, some of the best food in the world. It was challenging to narrow down my highlights, but after spending the better part of a decade living in the Windy City, these unique places to eat in Chicago are those I miss the most when I am away travelling.
This hot dog mural (located in the alley behind the Greetings mural) is an homage to the humble food item that is so engrained in Chicago’s culture and history. I recommend making ordering your dog “Chicago Style”, but however you order it, honour the locals by skipping the ketchup on your dog. Image © Brittany Lillegard
I have been telling people for years that Chicago is the best food city in America, and have even risked a few scuffles standing my ground with residents of other American cities that shall not be named. When both Conde Nast and Bon Appetit Magazines announced Chicago as the best restaurant city in America, it thrilled me that people were finally catching on. Known for dishes such as deep dish pizza, Italian beef sandwiches, the sweet and salty Garret Mix at Garret’s popcorn, and ketchup-free hot dogs (preferably all-beef, wrapped in a steamed poppy seed bun and topped with yellow mustard, onion, tomato, neon green relish, a dill pickle spear, a dash of celery salt and pickled sport pepper), residents of this city are just as comfortable in a fine dining setting as they are eating hot dogs in baseball caps and t-shirts. No matter how casual or high-end you choose to dine though, you will definitely want to spend some time eating your way through these must-try restaurants in Chicago.
Heritage Bicycles General Store is a great place to dream about your custom bicycle, grab a cup of coffee, and take a quick photo shoot in front of the mural honouring the 2016 World Series Champions, the Chicago Cubs. Image © Brittany Lillegard
Unique Places to Eat in Chicago
Heritage Bicycles General Store | Multiple Locations
Not only will you find my favourite cup of brew in the city at this location, but you can also get your bicycle serviced or have them build your dreamiest custom bicycle here too. The recently expanded original Lakeview location is an inviting space with beautiful natural lighting and a seriously friendly and knowledgable group of baristas. When you visit, don’t forget to leave the staff and fellow customers a love note on their old school typewriter and take a photo in front of the mural outside celebrating the 2016 World Series Champions, the Chicago Cubs. Can’t make it to Lakeview? You’re in luck as the Heritage family is quickly taking over the city (that’s a great thing) and have additional locations around the city.
A large mural painted on the side of Ipsento 606, which serves as the perfect coffee stop while you are taking in city views from the 606 Trail. Image © Brittany Lillegard
Ipsento | Multiple Locations
The original Ipsento location is a ridiculously cozy space that feels so much like home that you will be able to hunker down here for hours. Their second location, Ipsento 606, conveniently located right off the 606 trail, makes a great pitstop when you’re checking out the elevated outdoor park. I’m usually a black coffee kind of gal, but I have to admit that the Ipsento Latte, which is a concoction of coconut and dairy milk, cayenne pepper, honey, and espresso is dreamy enough to make me cheat on my usual coffee order every single time. At the 606 location, I dare you to resist ordering the adorable mini donuts that are conveniently located at eye level, right next to the registers.
Beermiscuous feels like a home away from home with one of the largest selections of craft beer in Chicago. Image © Brittany Lillegard
Beermiscuous | 2812 N Lincoln Avenue
Full Disclosure: I spent so much time here when I lived in the city, that I ended up working behind the counter as a Beerista before I left the city life behind to become a nomad. This beer cafe which feels like a home away from home boasts one of the largest selections of craft beer in Chicago and the general manager, Austin, might just be one of the most knowledgable beer experts stateside. I highly recommend heading in a on Wednesday when beer flights are half-off and nagging the seats by the cozy fireplace while you settle in for the evening. If you want to explore more of the Chicago beer scene, you will also want to grab a copy of the Beermiscuous Field Guide to Chicago Breweries on your way out and use it to help guide you as your tour Chicago’s best breweries.
The famous Oatmeal Shake is a must-try at Chicago’s vibrant and colourful Irazu Costa Rican Restaurant. Image © Brittany Lillegard
Irazu | 1865 N Milwaukee Avenue
A Chicago institution and one of the best places to eat in Chicago, Irazu serves up some seriously delicious Costa Rican food with a colourful and exciting vibe. The food here may look simple, but don’t let the simplicity fool you – every dish here is packed with vibrant flavour. I also have to confess I always order two meals when I visit – one for dinner and one to take home for the next day. You can’t go wrong with anything on the menu, but my standard go-to is the Vegetarian Plate with an extra side of plantains and the Oatmeal Shake, and trust me, you’ll want to order the oatmeal shake. Pro tip: Irazu is cash only and while there is an ATM inside, it is best to come prepared.
Piece Pizzeria | 1927 W North Avenue
Everyone comes to Chicago wanting to indulge in the city’s famous deep dish pizza, but I have a little secret for you – we are actually a city of thin crust lovers. My personal favourite pie in the city can be found at Piece Pizzeria and Brewery, and this also happens to be my welcome home meal every single time I return. A standard go-to spot for most Chicagoans, you’ll want to get here for an early dinner, even on weekdays, if you don’t want to wait in line. Top your pizza as you wish, but I happen to think that giardenira, a favourite pizza topping among locals, and Hot Doug’s Atomic Sausage is the dreamiest combo available. The world-famous Hot Doug’s Sausage Shop no longer exists (it took a little piece of my heart with it when it closed), but it is reassuring to know that you can still get a little taste of Chicago history with the atomic sausage that the famous encased meats guru, Doug Sohn, created specifically for Piece’s pies.
For seasonal American fare in a casual yet elegant neighbourhood setting, the White Oak Tavern and Inn is for you. Image © Brittany Lillegard
White Oak Inn + Tavern | 1200 W Webster Avenue
If you are looking for quality and seasonal American fare in a casual yet elegant neighbourhood setting, this is your place. More importantly though, this spot is home to my favourite Bloody Mary in the city (ask for it spicy) and if you’re stopping by for brunch, you would be remiss to skip the Cinnamon Roll. If you’re lucky enough to run into the owner, John, while you are there you can be assured that you will also be granted with some good conversation and the best dad jokes around. If you really want a neighbourhood experience, the Sunny Inn upstairs is available for vacation rentals and comes equipped with a ping pong table and skyline views.
Gilt Bar Chicago | 230 W Kinzie Street
Sister restaurant, Au Cheval, typically gets all of the attention these days, but Gilt Bar will always be my favourite in this well-known Chicago restaurant empire. Their small plates focused menu means the more friends you bring along, the more you get to sample. I highly recommend making sure the Roasted Bone Marrow ends up on your table and washing it down with a gin martini made with North Shore gin, one of the first of Chicago’s craft distilleries that helped pave the way for the extensive local spirits scene that exists today. To officially leave your mark on the Windy City, don’t forget to hit up the photo booth downstairs and pin your photo strip in the hallway (rumour has it, my face might be gracing the walls a few times). Insider’s Tip: In the same building, you’ll find the Doughnut Vault window that was partially responsible for launching Chicago into a donut craze a few years ago. The window has outlasted the trend, but this is still one of the best spots to start your day in Chicago. Get here early though because once they sell out, they close up shop for the day.
From the archives: The menu from my first time dining at El Ideas in 2012. The unique Michelin Star restaurant has changed a few things since then, but still offers diners creative fine dining in a relaxed and comfortable setting. Image © Brittany Lillegard
El Ideas | 2419 W 14th Street
Chicago boasts 26 Michelin stars and I can proudly say that I have sampled most of them for you, but if you are short on time or money, El Ideas, hands down is my favourite of them as one of the most unique places to eat in Chicago. After breaking up with one of Chicago’s classiest hotels, Chef Phillip Foss wandered the city for a few years in his first child, the Meatyball food truck. Meatyballs and the Chicago food truck scene never quite took off (RIP), but Chef Foss will still make you blush with his humour at his current space, El Ideas, where you will taste some of the most creative and delicious dishes in quite possibly the most fun and unpretentious fine dining setting you will ever find. The small space is structured such that diners are seated in view of the kitchen making them witnesses to the culinary magic that usually takes place behind the scenes. Courses are frequently delivered to the tables by Foss himself, and while you can guarantee that the food is of fine dining quality, don’t be surprised if you’re encouraged to forgo the utensils and use your hands or even have to lick the plate. This unique and memorable experience might just be one of the most fun dining experiences in the world and is not to miss on your Chicago visit.
Brittany is a traveling strength coach and yoga instructor from Chicago. She fuses her travel stories with her coaching background to help inspire and empower women to get comfortable with being uncomfortable, and to take charge of creating their own adventures.
She thrives off of coffee and wine, prefers to spend her days barefoot, and when she isn’t coaching or working on her handstand skills, she can be found plotting her next adventure.