Best December City Breaks: 48-Hour Itineraries
December offers a unique magic for urban explorers. The winter season transforms bustling cityscapes into festive wonderlands, with sparkling lights, the scent of mulled wine, and a palpable holiday spirit. A short city break is the perfect way to soak it all in. But with limited daylight hours and cold weather, a smart plan is essential for making the most of a 48-hour winter getaway.
This guide provides detailed two-day itineraries for three incredible cities: Chicago, Montreal, and Vienna. Each plan is designed to give you a perfect winter city break, balancing iconic sights with cozy indoor retreats, delicious food, and festive moments. From navigating public transport to packing efficiently, these tips will help you enjoy the best December city breaks without the stress. December is also a great time to find cheap flights to many winter destinations, making a spontaneous city break more accessible.
Introduction to City Breaks
When the winter season arrives, European cities transform into enchanting destinations perfect for a city break. Whether you’re drawn to the snow-covered rooftops of a medieval old town or the vibrant city life of a modern metropolis, winter city breaks offer something for every traveller. The best winter city breaks combine festive spirit, delicious food, and stunning architecture, making them ideal for a quick escape or a longer adventure. From the twinkling lights of Vienna to the cozy charm of Tallinn, city breaks in Europe during the colder months are filled with unique experiences. Whether you’re seeking a romantic getaway, a cultural exploration, or simply a change of scenery, there’s a winter city waiting to become your next favourite destination.
How to Choose Your Perfect Winter City Break
- Chicago: Best for lovers of grand architecture, world-class museums, and a classic American holiday feel. Expect freezing temperatures and a lively downtown.
- Montreal: Ideal for those seeking a European vibe closer to home, with historic cobbled streets, exceptional food, and bilingual charm. Prepare for a truly cold, snowy city break.
- Vienna: The top choice for anyone dreaming of traditional European Christmas markets, imperial history, and classical music. It's a fairy-tale winter destination.
Planning Your City Break
Planning the perfect winter city break starts with a bit of research and a dash of inspiration. Begin by listing your favourite winter city breaks and narrowing down your options based on your budget, travel time, and the kind of experiences you want—whether that’s exploring great Christmas markets, gliding across an ice skating rink, or sipping hot chocolate in a cozy café. Consider travelling during the quieter winter months to enjoy fewer crowds and better deals, or add a day trip to a nearby city for a fresh perspective. Look for cities that come alive with festive spirit, offering vibrant Christmas markets and plenty of winter activities. With a little planning, you can make the most of your city break and discover the magic of winter in Europe.
Chicago, USA: The Windy City’s Winter Sparkle
Chicago’s stunning architecture is even more dramatic against a winter sky. The city embraces the cold with vibrant energy, from ice skating with a skyline view to cozying up in world-class museums.
Quick Guide:
- Weather: Expect cold weather and freezing temperatures, often with biting wind. Average December temperatures range from 24°F to 35°F (-4°C to 2°C).
- Transit: The 'L' train system is efficient. Buy a Ventra card for easy tap-on-and-off payment on trains and buses. Most downtown sights are walkable, but rideshares are plentiful for cold nights.
Day 1: Magnificent Mile & Festive Lights
Morning: Start your day in Millennium Park. Take the obligatory photo with "The Bean" (Cloud Gate), which looks especially dramatic with a dusting of snow on the surrounding snow-covered rooftops. Afterward, embrace a beloved local tradition: ice skating at the McCormick Tribune Ice Rink, with the city’s skyscrapers as your backdrop.
Afternoon: Warm up with a walk through the Chicago Cultural Center (a free museum of sorts), a stunning building with the world’s largest Tiffany glass dome. From there, stroll north along the Magnificent Mile. Admire the spectacular window displays and the festive spirit of the Christmas lights that adorn the trees along the famous avenue.
Evening: Head to the Christkindlmarket in Daley Plaza, one of the best and most authentic Christmas markets in the US. Sip on hot chocolate or mulled wine from a souvenir mug and browse the traditional crafts. For dinner, indulge in a Chicago classic: deep-dish pizza at Lou Malnati's or Giordano's.
Day 2: Museum Campus & Neighborhood Charm
Morning: Dedicate your morning to the Museum Campus. Choose one of the city's incredible institutions: the Art Institute of Chicago (don’t miss the Thorne Miniature Rooms decorated for Christmas), the Field Museum for natural history, or the Shedd Aquarium. Book tickets in advance to save time.
Afternoon: Explore a different side of city life in the Wicker Park neighborhood. Take the 'L' Blue Line from downtown. This area is known for its independent boutiques, cozy cafes perfect for escaping the cold, and vibrant street art. It's a great place to find unique gifts and experience a more local vibe.
Evening: For your final night, enjoy a show in the Theater District. From Broadway productions to local plays, there's always something on. Afterward, enjoy a late-night dinner at a cosy restaurant in the trendy West Loop area, known for its amazing and delicious food scene.
Must-Eat: Deep-dish pizza, a Chicago-style hot dog (no ketchup!), Garrett Popcorn.
Must-See: The Bean (Cloud Gate), Museum Campus, the view from the Willis Tower or 360 Chicago.
Montreal, Canada: A Snowy European Escape
With its French-speaking locals, historic Old Town, and incredible food scene, Montreal feels like one of the best European winter city breaks without the long flight. The city becomes a true winter wonderland under a blanket of snow. Visiting in early January means fewer tourists and a more relaxed atmosphere, making it an ideal time for a winter city break.
Quick Guide:
- Weather: Montreal has cold winters. Expect snow and temperatures often dropping to between 9°F and 23°F (-13°C to -5°C). Dress in warm layers.
- Transit: The Metro system is clean and efficient. A 3-day pass offers great value. Old Montreal is very walkable, and the “Underground City” (RÉSO) connects malls, metro stations, and buildings, offering a warm way to get around.
Day 1: Old World Charm & Festive Markets
Morning: Begin in Old Montreal (Vieux-Montréal). Wander the charming cobbled streets, admiring the 18th-century architecture. Visit the stunning Notre-Dame Basilica (book tickets online). The historic old town square, Place Jacques-Cartier, is especially festive during the holiday season.
Afternoon: Head to the Atwater Market, which hosts a magical Christmas market. Sample traditional food from local vendors and enjoy the lively atmosphere. Afterward, warm up with a walk along the Lachine Canal, which is often frozen and beautiful in the winter time.
Evening: Experience the festive spirit at Montréal en Fêtes (Merry Montreal) in the Old Port, featuring outdoor bars, music, and a grand New Year's Eve festival if your trip aligns. Enjoy ice skating on the refrigerated rink with beautiful city views. For dinner, find a cosy restaurant in the Old Town for some classic French-Canadian fare.
Day 2: Mountain Views & Modern Culture
Morning: Take a short bus ride or a brisk walk up to Mount Royal Park, the city’s namesake. A walk to the Kondiaronk Belvedere lookout rewards you with a panoramic view of the entire city skyline against the winter landscape. It’s a perfect spot for photos.
Afternoon: Descend into the Plateau Mont-Royal neighborhood, known for its colourful houses and colorful houses with spiral staircases. Explore the boutiques on Saint-Denis Street and Mont-Royal Avenue. Stop at one of the many cozy cafes for a hot chocolate to warm up from the freezing temperatures.
Evening: For your last night, immerse yourself in modern Montreal culture in the Quartier des Spectacles. This vibrant city district hosts Luminothérapie, an interactive outdoor exhibit of sparkling lights and art installations during the winter months, turning the dark nights into a playground. Enjoy dinner at a bistro in the area before you depart.
Must-Eat: Poutine (fries, cheese curds, gravy), a Montreal-style bagel (from St-Viateur or Fairmount), smoked meat sandwich. Must-See: Old Montreal and Notre-Dame Basilica, Mount Royal Park lookout, Jean-Talon or Atwater Market.
Vienna, Austria: An Imperial Winter Dream
As the former capital city of an empire, Vienna’s grandeur is undeniable. During the winter season, it transforms into one of the most magical European winter destinations, famous for its elegant Christmas markets and classical music traditions.
Quick Guide:
- Weather: Cold and often overcast, with a chance of snow. Temperatures typically range from 30°F to 39°F (-1°C to 4°C).
- Transit: The public transport system (U-Bahn, trams, buses) is excellent. A 48-hour or 72-hour pass is the most convenient and cost-effective option. The city centre (First District) is very walkable.
Day 1: Imperial Palaces & Christmas Markets
Morning: Start in the heart of the city at St. Stephen's Cathedral, an icon of Vienna. Climb the South Tower for a breathtaking view of the city's snow-covered rooftops. From there, wander through the Hofburg Palace complex, the former residence of the Habsburg emperors.
Afternoon: Immerse yourself in the Christmas spirit at the Viennese Dream Christmas Market in front of City Hall (Rathausplatz). This is one of the great Christmas markets in Europe, with an ice rink, countless stalls, and stunning decorations. It is the perfect winter city break experience.
Evening: Attend a classical music concert. Vienna is the city of music, and hearing a Mozart or Strauss performance in a historic venue is an unforgettable experience. Afterward, enjoy a traditional dinner of Wiener Schnitzel at a classic Viennese "beisl" (bistro).
Day 2: Artistic Treasures & Sweet Treats
Morning: Explore the MuseumsQuartier, one of the world's largest art and culture complexes. Choose between the Leopold Museum, which houses an incredible collection of Austrian art, or the MUMOK for modern art. Many of Vienna’s museums offer exceptional value.
Afternoon: Visit the magnificent Schönbrunn Palace, the former imperial summer residence. Even in winter, the palace and its grounds are stunning. A cultural Christmas market is also held in the palace forecourt. Afterward, indulge in a classic Viennese coffee house experience. Order a slice of Sachertorte and a "melange" (coffee) and enjoy the elegant, old-world atmosphere at Café Central or Café Sacher.
Evening: For your final evening, visit another charming Christmas market, like the one at Karlsplatz, known for its focus on local artisans, or the Spittelberg market, tucked away in romantic, narrow streets. Enjoy a final mug of mulled wine to celebrate your winter escape.
Must-Eat: Wiener Schnitzel, Sachertorte (chocolate cake), Apfelstrudel.
Must-See: St. Stephen's Cathedral, Schönbrunn Palace, the Rathausplatz Christmas Market.
Winter Breaks and Hot Springs
There’s nothing quite like warming up in a steaming hot spring or thermal bath after a day of winter sightseeing. Many European cities, such as Budapest and Prague, are renowned for their historic thermal baths, where you can soak in mineral-rich waters surrounded by stunning architecture. These relaxing retreats are the perfect complement to a winter city break, offering a soothing escape from the cold and a chance to unwind in style. For a more off-the-beaten-path experience, head to Eastern Hungary, where you’ll find some of the best hot springs in Europe—ideal for a rejuvenating winter break that won’t break the bank. Whether you’re looking to relax after exploring the city or simply want to enjoy the unique atmosphere of a traditional bathhouse, hot springs are a must for any winter city break itinerary.
Lake Bled: A Unique Winter Destination
For a truly unforgettable winter city break, look no further than Lake Bled in Slovenia. This enchanting winter city is a hidden gem, offering a magical blend of natural beauty and old-world charm. The town square and old town come alive in the colder months, with snow-covered mountains providing a breathtaking backdrop to the frozen lake. Visitors can enjoy classic winter activities like ice skating, skiing, and snowshoeing, or simply stroll around the lake and soak in the serene atmosphere. After a day of adventure, warm up in one of Lake Bled’s renowned thermal baths or hot springs, the perfect way to relax and recharge. Whether you’re seeking romance, relaxation, or a bit of winter fun, Lake Bled is an incredible destination that deserves a spot on every winter travel bucket list.
Winter City Break Packing Checklist
Packing smart is key for a short trip.
- Warm, waterproof winter coat
- Waterproof boots with good traction
- Thermal base layers
- Hat, gloves, and a scarf
- Wool socks (bring an extra pair!)
- Portable charger for your phone
- Silicone luggage tag for easy bag identification
- Compact travel laundry bag to keep dirty clothes separate in your carry-on
