A Perfect Winter Day In Chicago


Despite the chill in the air, there’s no shortage of things to do and see, from indoor activities like museum visits and shopping to outdoor fun like ice-skating and winter sports. In this article, we’ll guide you through a perfect winter day in Chicago, taking in the best of what the city has to offer during this cozy season. From brunch and coffee to outdoor adventures and evening entertainment, we’ve got you covered for a day you’ll never forget. So, whether you’re a local or just visiting, be sure to follow this guide to experience the very best of what winter has to offer in Chicago.

9:00 am – Sleep In and Head to Our Favorite Brunch Spot

Yolk specializes in our favorite comforting brunch foods. In 2006, Taki Kastanis opened Yolk in Chicago’s South Loop. Yolk quickly became a Chicago favorite and expanded to many locations across the city. Yolk’s menu is diverse and approachable, satisfying every sweet or savory tooth. Check out their “Fan Favorites” section on the menu to see why this brunch spot is our go-to. 

11:00 am – See Well-known Chicago Exhibits

After enjoying a delicious brunch, head over to the Skydeck at Willis Tower! You’ll see Chicago from a new point of view and get out of the cold, all in one stop. Step onto The Ledge of the third tallest building in the Western Hemisphere and be amazed at a 360° view of Chicago. The lines will be shorter in the winter so it’s the perfect time to plan your visit! Instead of feeling the cold, see it from a different, warmer angle at the Skydeck.

If you’re a fan of ocean life, Shedd Aquarium is the ultimate. Get up close and personal with thousands of aquatic creatures and be prepared to learn a lot! Committed to compassion for animals, conservation of habitats, and curiosity about the world, Shedd is a highlight of any visit to Chicago.

1:00 pm – Lunch and Shopping

See Lake Michigan’s icy glory from inside Navy Pier! This waterfront destination is an ideal spot to do some indoor shopping – and you’ll have plenty of restaurants to choose from along the way. Navy Pier has it all, from beloved vendors like Garrett’s Popcorn, to places off the beaten path like AMRI Juice Bar. Before you leave, grab some Chicago-centric creations to remember your visit. 

If you’re in pursuit of great pizza, mere steps away from Navy Pier you will find Robert’s. With a chewy center and a crispy crust, Robert’s brick-oven baked, thin-crust artisan pizza has been perfected over 20 years. Their hours span most of the day, so there’s ample time to get in on this delicious Chicago favorite. Robert’s also offers unique brunch and dessert pizzas. And when you enjoy a slice at Robert’s, you get upgraded classic and inventive cocktails. 

4:00 pm – Experience Art at Chicago’s Cultural Center

For a chance to get off your feet in beautiful surroundings, head to Chicago’s Cultural Center for a relaxed approach to Chicago’s art scene. The Cultural Center offers a wide variety of programming, including dance and music performances, discussions with artists, architecture tours, and galleries of historic art. They also have a learning lab to get minds thinking! This must-experience Chicago spot is open daily, 10 AM-5 PM. 

6:30 pm – Enjoy Dinner with Chicago Flavors 

If you’re looking for an upscale restaurant, check out the spectacular views of world famous Millennium Park from three levels at Rosebud Randolph. Choose the first or second floor for casual or quiet, refined dining. Savor the classic Italian menu, from antipasti to insalate to fine steaks, pastas, and seafood. Select from the extensive wine list and decadent dessert

menu. Complete your perfect day with a cocktail on the rooftop.

Written by Maddie Belland

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