You are the writer, director, producer and lead actor in your life story. Your set is the city of Chicago, and it’s time you start utilizing it. The city of hard workers, untouchable summers, and hidden romantic gems, there’s no better place than Chicago to start romanticizing your life.
An internet trend that arose during the height of the pandemic, romanticizing your life is all about living in the moment, smelling the roses and appreciating life’s simple pleasures—and luckily for us, Chicago’s full of neighborhoods where you can plan a whole day around making your life a little more romantic. From walking around your city with hot cocoa in hand to ice skating during the first snowfall, lean into your main character energy this winter and explore six ways to romanticize your life in Chicago.
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1. West Loop
Main stops: Cira and Levain Bakery
With its bustling energy and boundless supply of aesthetically pleasing dining options, the West Loop is a must-visit destination if you’re on a journey to romanticize your life. Stumped on where to eat? Trying popping by Cira, a modern, well-designed Mediterranean eatery that looks like one of those places you see in the movies. From the high ceilings to the clean yet inviting decor, this is the perfect place to sit at the bar, order some brown butter hummus and people-watch. Stop at Levain Bakery, an NYC import and the new “it girl “of bakeries, on your way home and pick up some goodies—there’s plenty to choose from, but you can never go wrong with the famous chocolate chip walnut cookies.
2. The Loop
Main stops: American Writers Museum and The Magnificent Mile
When Frank Sinatra declared his love for Chicago, he was talking about downtown (State Street, that great street!). Harness that jazzy energy when you head to the Loop and journey into the mystical world of words at the American Writers Museum. Visit the ongoing “Dark Testament: A Century of Black Writers on Justice” exhibit and explore the works of Black authors and their large contribution to American literature and history. After you learn about the greats, keep walking along the Magnificent Mile and do some window shopping for the holidays. From toy holiday displays in department store windows to the luxurious offerings on display at shops like Saks, Burberry, and Bloomingdales, the Mag Mile is the perfect way to end your day of romanticization in Chicago.
3. Wicker Park
Main stops: Mindy’s Bakery and Volumes Bookcafe
If you’re seeking an artsy way to romanticize your life, look no further than Wicker Park, the neighborhood home to artists, hipsters and everything in between. Start your day at Mindy’s Bakery, the newly-opened project from pastry chef Mindy Segal. Grab a cup of their beloved cocoa—only sold on Saturday and Sunday—and a fresh pastry. After leaving Mindy’s, walk down to Volumes Bookcafe (the long-running bookstore that reopened in a new location earlier this year) and be prepared to dive into the world of a good read. Grab a book, take a seat and get lost in the world of literature.
4. Pilsen
Main stops: Harrison Park and Semillas Plant Studio
You could easily spend a whole day exploring Pilsen, which hosts some of the city’s most extensive and beautiful street art. Start by checking out the sights and sounds of Harrison Park, where you’ll find everything from vendors selling street corn to dogs playing with their owners. Want to bring a bit of the natural world home with you? After you leave the park, head to Semillas Plant Studio—good vibes and divinity radiate out of this boho, earthy plant shop. Go ahead and buy yourself some flowers or, if you’re worried about the low light of Chicago winters, a resilient snake plant. You deserve it.
5. South Loop
Main stops: Lotus Den and TeapotBrew Bakery
If you’re in need of some good energy, spend the day in the South Loop and check out the Lotus Den. The crystals shop of all crystal shops, this holistic healing boutique is filled with goodies to guide you on your path of realignment and self-discovery. After you buy some sage to cleanse your space going into the new year and some amethyst to help you manifest, head over to the TeapotBrew Bakery. This tea shop is intimate, and the smell of fresh baked goods and obscure yet aromatic tea blends hit you once you walk in. Indulge in their turmeric chai tea and try one of their melt-in-your-mouth scones.
6. Hyde Park
Main stops: Midway Plaisance and Virtue
The birthplace of Michelle and Barack Obama’s love story, the South Side of Chicago has many gems, and the entire neighborhood of Hyde Park is one of them. Get dressed up, put on your warmest and most flattering coat, and hit the ice at Midway Plaisance with your friends. Fall, laugh, and do a twirl if you can—and best of all, it’s only $7 to rent a pair of skates if you don’t have one at home. After this fun workout, head to Virtue, helmed by the James Beard Award-winning chef Erick Williams, for a comfort meal like you’ve never had before. This dimly intimate eatery is perfect for a friend date, a romantic date or a much-needed solo date.