6 Ways to Romanticize Your Life in Chicago this Winter

You are the author, director, producer and leading actor of your life story. Your set is the city of Chicago, and it’s time to use it. The city of hard workers, untouchable summers, and hidden romantic gems, there’s no better place than Chicago to start the romance of a lifetime.

An internet trend that emerged during the peak of the pandemic about romanticizing life, living in the moment, smelling the roses and embracing life’s simple pleasures – and luckily for us, Chicago is full of Neighborhoods where you can spend a whole day trying to make your life a little more romantic. From strolling around town with hot cocoa in hand to ice skating during the first snowfall, lean into your protagonist’s energy this winter and discover six ways to romanticize your life in Chicago.

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Cira's dining area
Photo: Courtesy of Boka Restaurant Group

1. West loop

Main stops: Bakery Cira and Levain

With its bustling energy and limitless array of aesthetically pleasing restaurants, the West Loop is a must-see if you’re on a journey to romance your life. Stumbled upon where to eat? Try stopping 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 but inviting decor, this is the perfect place to sit at the bar, order brown butter hummus and people-watch. On your way home, stop at Levain Bakery, a New York import and the new It-Girl of bakeries, and grab some treats — there’s plenty to choose from, but you’ll never fail with the famous chocolate chip walnut biscuits do wrong.

People explore exhibits at the American Writers Museum
Photo: Bob Wolgemuth

2. The loop

Main stops: American Writers Museum and The Magnificent Mile

When Frank Sinatra declared his love for Chicago, he spoke of 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 exhibition, Dark Testament: A Century of Black Writers on Justice, and explore the works of black authors and their major contribution to American literature and history. After learning about the greats, continue down the Magnificent Mile and window shop for the holidays. From toy displays in department store windows to the luxury offerings at stores like Saks, Burberry and Bloomingdales, the Mag Mile is the perfect way to end your romantic day in Chicago.

Pastries and bagels are available behind the counter at Mindy's Bakery
Aliza J. Sokolov

3. Willow Park

Main stops: Mindy’s Bakery and Volumes Bookcafe

If you’re looking for an artistic way to romanticize your life, look no further than Wicker Park, the neighborhood that’s home to artists, hipsters and everything in between. Start your day at Mindy’s Bakery, the newly opened venture of Master Pastry Chef Mindy Segal. Grab a cup of their beloved cocoa – only sold on Saturdays and Sundays – and a fresh pastry. After exiting Mindy’s, head down to the Volumes Bookcafe (the veteran bookshop that reopened in a new location earlier this year). and be ready to plunge into the world of good reading. Grab a book, take a seat and lose yourself in the world of literature.

A plant shop with shelves and plants hanging from the ceiling
Photo: Courtesy of Semillas Plant Shop

4. Pilsen

Main stops: Harrison Park and Semillas Plant Studio

You could easily spend a whole day exploring Pilsen, which is home to some of the most extensive and beautiful street art in the city. 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. Would you like to take a piece of nature home with you? After exiting the park, head to the Semillas Plant Studio – good vibes and divinity exude from this boho-earthy plant shop. Go ahead and buy yourself some flowers, or if you’re concerned about the dim light of Chicago winters, a hardy snake plant. You deserve it.

The interior of the Lotus Den crystal store
Photo: J’Mar White

5. South Loop

Main stops: Lotus Den and TeapotBrew Bakery

If you need good energy, spend the day at the Südschleife and see the lotus cave. The crystal store of all crystal stores, this holistic healing boutique is filled with goodies to guide you on your journey of realignment and self-discovery. After purchasing some Sage to cleanse your space for the New Year and some Amethyst to help you manifest, head to the TeapotBrew Bakery. This tea shop is intimate and the smell of freshly baked goods and obscure but aromatic tea blends grabs you as soon as you enter. Treat yourself to their turmeric chai tea and try one of their melt-in-the-mouth scones.

Virtue, Interior, Barry Crowbar
Photo: Barry Crowbar

6. Hyde Park

Main stops: Midway Plaisance and Virtue

The birthplace of Michelle and Barack Obama’s love story, Chicago’s South Side has many gems, and the entire Hyde Park neighborhood is one of them. Dress smartly, don your warmest, most flattering coat, and hit the ice with your friends at Midway Plaisance. Fall, laugh, and spin when you can—and best of all, it’s only $7 to rent a pair of skates if you don’t have any at home. After this fun workout, head to Virtue for a leisurely meal like you’ve never had under the direction of James Beard Award-winning chef Erick Williams. This faintly intimate spot is perfect for a date with friends, a romantic date, or a much-needed solo date.

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