Chicago, the Windy City, is a fantastic destination for a winter weekend break with your family. With its vibrant culture, iconic landmarks, and a unique blend of modern and historic charm, Chicago offers a wide array of activities for visitors of all ages. In this blog post, we’ll help you plan three perfect days in Chicago, packed with winter-themed adventures, cultural experiences, and mouthwatering cuisine.
Staying at our Chicago vacation rentals on the Near North Side gives you the perfect home base for exploring the city with your family.
Day 1: Explore the Magic of Millennium Park
Morning: Breakfast at a classic Chicago diner Start your day with a hearty breakfast at Original Pancake House, known for its mouthwatering oven baked apple pancake (ok, we know, it’s really dessert and should probably be ordered to share after a more “traditional” breakfast!). If Greek diners are more your thing, Tempo at State & Chestnut offers a variety of breakfast options. Either is the perfect place to fuel up for an exciting day ahead.
Late Morning: Millennium Park After breakfast, make your way to Millennium Park, an iconic urban park that comes alive during the winter months. Bundle up in your warmest coats and gloves and head to Cloud Gate, also known as “The Bean.” This reflective sculpture is a must-see and provides the perfect opportunity for family photos. Nearby, the Crown Fountain is a popular spot for kids to play in the shallow reflecting pool (seasonal).
Afternoon: The Art Institute of Chicago Warm up indoors by visiting the renowned Art Institute of Chicago, located just across from Millennium Park. This world-class museum houses an impressive collection of art from various eras and cultures. Don’t forget to check out the Thorne Miniature Rooms, a fascinating exhibit for children and adults alike.
Lunch: The Gage For lunch, head to The Gage, a cozy restaurant located near Millennium Park. They offer a diverse menu with options for the whole family, from burgers to salads.
Late Afternoon: Ice Skating at Maggie Daley Park Embrace the winter spirit with some ice skating at Maggie Daley Park, located adjacent to Millennium Park. The skating ribbon winds through a beautiful winter landscape, providing a unique ice skating experience. Skate rentals are available, and it’s a delightful activity for all skill levels.
Dinner: Chicago’s famous deep-dish pizza If you’re ready for a rest, and you’re staying in one of our Magic Factory Lofts, consider taking advantage of the space to relax & dine at home. There’s no shortage of opinions about Chicago’s best deep dish pizza. Nearby options for deliver include Lou Malnatti’s, Pizano’s, Uno’s and Giordano’s.
Day 2: Journey through Chicago’s Museums
Morning: Breakfast at Yolk Kick off your second day with a delicious breakfast at Yolk, a popular breakfast spot known for its creative omelets and tasty pancakes.
Late Morning: Field Museum of Natural History Explore the wonders of natural history at the Field Museum. With captivating exhibits featuring dinosaurs, ancient civilizations, and a massive collection of artifacts, it’s a captivating experience for both kids and adults.
Afternoon: Adler Planetarium and Shedd Aquarium Located nearby, the Adler Planetarium and Shedd Aquarium are two more family-friendly destinations worth visiting. Marvel at the stars and galaxies at the planetarium and then dive into the underwater world of the aquarium. These attractions are sure to leave your family in awe.
Late Afternoon: Navy Pier Head to Navy Pier to explore Navy Pier’s winter attractions, including the indoor botanical garden at the Crystal Gardens and the Centennial Wheel for breathtaking views of Lake Michigan.
Chicago Children’s Museum Continue your family adventure by visiting the Chicago Children’s Museum, also located at Navy Pier. It offers interactive exhibits and hands-on activities that engage kids’ imaginations and keep them entertained for hours. If your children are older, and you’re visiting before January 7, 2024, explore the Pier’s outdoor skating, live music performances, settle around the fire pits and roast s’mores or take a ride around the heated Centennial Ferris Wheel.
Most of these great attractions are easily reachable when you’re staying close by — learn more about our centrally located loft rentals and neighborhood.
Visiting Chicago with a group of friends and family? There’s also the Lakefront Lodge, open until the end of February 2024 where you can book a private curling rink, heated igloo, hot chocolate bar and firepit.
Dinner: Harry Caray’s Tavern – Navy Pier or options in the food hall. If you are ready to relax casually & refuel before ending your day, try a classic Chicago “cheezborger” at Billy Goat Tavern, or indulge in fried chicken and ice cream floats at Big City Chicken
Day 3: Winter Wonderland and Cultural Exploration
Morning: Breakfast at Cornerstone Cafe or Dash of Salt & Pepper Start your day with a wholesome breakfast at one of 2 of our favorite Lincoln Park breakfast. Both restaurants are locally owned, non-chain/franchised breakfast/lunch spots offer fresh and healthy menu options, great coffee and no pretense.
Late Morning: Lincoln Park Zoo Spend the morning at Lincoln Park Zoo, which remains open during the winter months. It’s a delightful place to see animals from around the world in a picturesque setting. Best of all, admission is free!
Afternoon: Lincoln Park Conservatory Adjacent to the zoo is the Lincoln Park Conservatory, a warm and lush escape from the winter chill. Explore the various greenhouse rooms filled with exotic plants, making it an educational and visually stunning experience for the whole family.
Lunch: RJ Grunts Head to RJ Grunts, a family-friendly restaurant in Lincoln Park known for its burgers and shakes. The laid-back atmosphere and diverse menu make it a great choice for a relaxing meal.
Late Afternoon: Chicago History Museum Delve into the city’s rich history at the Chicago History Museum. Its interactive exhibits and engaging displays make learning about Chicago’s past fun for both kids and adults.
Dinner: Portillo’s End your Chicago winter weekend break with a classic Chicago-style hot dog or Italian beef sandwich at Portillo’s. Or wander down Wells Street in Old Town for Chicago’s favorite burger at Small Cheval. It’s a local institution and a tasty way to wrap up your trip.
Yes, that was a very quick Chicago winter weekend break!
Chicago offers an incredible array of activities for families during the winter months. From exploring iconic landmarks to visiting world-class museums and enjoying hearty Chicago cuisine, your family is sure to create unforgettable memories during a weekend getaway in the Windy City. Bundle up, embrace the winter wonderland, and savor the vibrant culture of Chicago with your loved ones.
And of course, if you’re looking for accommodation in the Chicago, Magic Factory Lofts family friendly Airbnb style vacation rentals are the perfect base from which to explore!