Curator’s statement
A winter weekend in Chicago is a mosaic of unique experiences that resonate deeply with me. From savoring Chicago-style pizza to gliding across the ice at Maggie Daley Park, each moment is filled with a sense of wonder. The city comes alive with festive lights and the whimsical Christmas train, while Navy Pier's Christmas market offers treasures and delights. Atop it all, an igloo rooftop bar provides a breathtaking view of the illuminated skyline. And to cap it off, a Christmas show at the theater immerses me in the joy of the season. These moments, culminating with a steaming cup of hot chocolate at Christkindlmarket, fill me with gratitude for the magic found in the heart of the city.
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Things to do in Chicago
Attractions/Museums:
Skydeck Chicago: Experience breathtaking views of the city skyline from the iconic Skydeck Chicago, especially magical during the winter with the city adorned in holiday lights.
Shedd Aquarium: Explore the wonders of the aquatic world with a visit to Shedd Aquarium, where you can marvel at diverse marine life and immersive exhibits, perfect for all ages.
Chicago Art Institute Museum: Immerse yourself in art and culture at the Chicago Art Institute Museum, featuring renowned collections and special exhibitions.
Field Museum: Embark on a journey through natural history and cultural heritage at the Field Museum, offering engaging exhibits and educational experiences that are sure to captivate visitors of all ages.
Theater/Entertainment:
Goodman Theater: Be transported into the world of captivating performances at Goodman Theater, where winter months bring a lineup of heartwarming holiday productions and timeless classics.
Chicago Theater: Experience the magic of live entertainment at the historic Chicago Theater, offering a variety of holiday-themed shows and musical performances to enchant audiences.
Second City Improv Show: Experience laughter and creativity at its finest with a Second City improv show, where talented comedians deliver hilarious performances that are perfect for livening up your winter weekend in Chicago.
Outdoor Activities:
Navy Pier: Delight in the festive atmosphere at Navy Pier, where you can enjoy seasonal attractions, holiday shopping and enchanting light displays along Lake Michigan.
Architecture River Cruise Tour: Embark on an unforgettable journey along the Chicago River with an architecture river cruise tour, where you can admire the city's iconic skyline and learn about its rich architectural history from knowledgeable guides, offering a unique perspective of Chicago's beauty. Bundle up and sip on hot cocoa while you look up at the beautiful buildings.
Ice Skating Ribbon at Maggie Daley Park: Glide across the ice at the Ice Skating Ribbon in Maggie Daley Park, surrounded by the stunning city skyline and festive decorations, creating a picture-perfect winter experience. Grab a skating buddy if you need help gliding along (kids and adults alike)!
IO Godfrey Rooftop Igloo Winter Wonderland Experience: Elevate your winter weekend with a visit to the IO Godfrey Rooftop Igloo, where you can cozy up in a heated igloo while enjoying panoramic views of the cityscape adorned in holiday lights. When you make a reservation you'll have to order a bottle to make the reservation (I recommend champagne) then while you're there get their charcuterie board!
Holiday Market:
Christkindlmarket: Immerse yourself in the festive spirit at Christkindlmarket, a traditional German holiday market featuring charming wooden stalls, authentic holiday treats and unique gifts, creating a magical atmosphere reminiscent of a European winter wonderland. This is a must for a winter weekend in Chicago!
Places to eat & drink in Chicago
Breakfast:
Wildberry Pancakes & Cafe: Treat yourself to a delightful breakfast or brunch experience at Wildberry Pancakes & Cafe, where you can enjoy fluffy pancakes and hearty breakfast fare, which will fuel your winter adventures in Chicago. Try the classic benedict and ask for a side of the signature berry bliss pancakes - the best of both worlds (in my opinion).
Kanela Breakfast Club: Begin your winter morning with a hearty and satisfying breakfast at Kanela Breakfast Club, where you can savor the warmth of dishes like fluffy pancakes, indulgent eggs Benedict and savory breakfast skillets. All of which are served with a side of cozy ambiance and friendly service, making it the perfect spot to start your winter day in Chicago. Try the fried chicken and waffles.
Lunch:
Al's Beef: Dive into Chicago's iconic Italian beef sandwiches at Al's Beef, where juicy, flavorful beef piled high on crusty bread provides the ultimate comfort food indulgence during the chilly winter weather. Get the Italian Beef with hot and sweet peppers, dunked! Yum!
Billy Goat Tavern: Enjoy a taste of Chicago history at Billy Goat Tavern, where you can sink your teeth into delicious cheeseburgers and classic pub fare in a lively and nostalgic atmosphere, perfect for a casual meal or snack during your winter weekend.
Lunch/Dinner:
Lou Malnati's Pizza: Delight in Chicago's famous deep-dish pizza at Lou Malnati's, where buttery crust, gooey cheese and savory toppings come together in a mouthwatering masterpiece that's sure to warm you up on a cold December day.
Dinner:
La Pizza & La Pasta: Indulge in authentic Italian flavors at La Pizza & La Pasta, where you can savor delicious pizzas and pastas in a cozy and inviting atmosphere. It's the perfect spot for warming up during the winter months. Try the table-side fettuccini - fun and delicious choice!.
Dinner/Bars:
IO Godfrey Rooftop Bar Winter Wonderland: Elevate your winter weekend with a visit to IO Godfrey Rooftop Bar which is transformed into a winter wonderland each year. It's complete with cozy igloos, festive cocktails and stunning views of the city skyline, offering a magical rooftop experience that's perfect for the holiday season.
1959 Kitchen and Bar: Experience contemporary American cuisine with a creative twist at 1959 Kitchen and Bar, offering innovative dishes and craft cocktails in a stylish setting. This spot is ideal for a memorable dining experience during December.
Need to know
I have an itinerary I used for a 2023 trip over a 4 day-weekend.
Staying at the Fairmont Chicago - Millennium Park, getting to experience their Lodge (a cabin-esque vibe in their lobby), and seeing the park and city views (with direct access to the Christmas train that would pass by) definitely added to the Chicago experience.
If you get a chance to see the Christmas Carol, this was a phenomenal show at the Goodman Theatre. A comedy skit at Second City was a perfect night kick off to the rooftop bar experience (where you must get the bottle service!).
Grab a cup of hot cocoa in a souvenir cup at the Christkindlmarket to sip on as you walk around - don't forget to swing through the candy spot, and grab a pretzel!
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Travel Advisor
Lauren McClemens
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This guide is part of our ongoing series on travel to Chicago. For more travel tips, check out Fora Advisor Ella Birman guide, The Chicago Guide for Art Lovers and Art Collectors.