Immersive Broad Introduction
Every December, the United States slips quietly into its most cinematic phase of the year. The familiar hum of ordinary life softens under the glow of string lights, city squares transform into winter villages, and travelers follow the scent of roasted chestnuts, hot cocoa, and pine wherever it leads. Whether it’s the hush of falling snow in New England or the warm, salty breeze of a Floridian Christmas, the holiday season in America brings a unique brand of magic — a sensory journey across lights, laughter, and beloved traditions.
Families pack their coats, couples plan anniversary escapes, and solo wanderers chase new postcards for the memory book. And thanks to modern, seamless travel options like flights from New York, flights from California, and flights from Florida, holiday travel feels less like a logistical challenge and more like a curated adventure waiting for departure.
Below, we take you through the most beloved U.S. winter markets and holiday destinations — the places that make Christmas more than a date on the calendar.
Cities Covered
This blog highlights the top U.S. winter markets and festive getaways ideal for a December trip, whether for shopping, sightseeing, family bonding, or seasonal magic. Each destination offers something distinct — snowy storybook landscapes, Southern hospitality, coastal wonderlands, or sunshine in December if you prefer tinsel over snowflakes.
- New York City, New York
- Chicago, Illinois
- Bethlehem, Pennsylvania
- Denver, Colorado
- San Francisco, California
- Orlando, Florida
1. New York City – When Holidays Become a Movie Set
There is no holiday destination on Earth quite like New York in December. Bryant Park becomes a snowy winter carnival, the Rockefeller tree towers over the city like a glowing compass, and Fifth Avenue displays turn shopping into theatre. Visitors love hopping between Bryant Park’s Winter Village, Union Square Holiday Market, and Columbus Circle’s world-class open-air fair.
NYC in December is endlessly walkable, but even more accessible with convenient travel routes like flights from New York for return legs or connecting multi-city journeys. Many travelers pair the trip with coastal escapes thanks to seasonal deals on flights from Florida — perfect for a New York winter followed by a Miami warm-up.
Practical pointers
Book ice-skating slots in advance, visit markets early in the day to avoid peak crowds, and keep room in your luggage — NYC markets are famously irresistible.
2. Chicago – The Midwestern Capital of Holiday Charm
Forget postcards — Chicago is the postcard. In December, the city becomes a grand architectural snow globe with its legendary Christkindlmarket at the center. Imported German ornaments, potato pancakes, pretzels, and steaming glühwein make this one of the most authentic European-style markets in the U.S.
A popular hop-between destination for multi-city travelers, Chicago pairs beautifully with snowy East Coast itineraries, especially using easy routes that begin with flights from New York or end with December sunshine via flights from California.
Practical pointers
Bring warm layers — Chicago winter is real winter. Book market dining huts early and explore the Riverwalk for gorgeous holiday photos.
3. Bethlehem, Pennsylvania – Christmas City USA
A holiday town that takes its name seriously, Bethlehem looks like something conjured by a greeting-card designer. Its Christmas Village glows with Moravian stars, artisan booths, carolers, and candlelit cobblestone streets. It has become a favorite for families wanting a quieter, deeply traditional Christmas setting.
Many travelers create hybrid holiday trips with Bethlehem as the calm finale to the city rush — a perfect pairing with flights from New York for the inbound leg or southern holiday journeys supported by flights from Florida.
Practical pointers
Arrive close to sunset — the town is breathtaking when the lights come on. Don’t leave without a handcrafted Moravian star ornament.
4. Denver – A Rocky Mountain Winter Wonderland
Denver serves a Christmas aesthetic with an alpine twist. The Denver Christkindlmarket brings Bavarian charm while the city’s local artists fill stalls with leatherwork, pottery, mountain-themed décor, and cozy apparel perfect for winter gifting.
Multi-city travelers love pairing Denver with coastal holiday escapes using easy route combinations that begin with flights from California or round-trip links through flights from New York.
Practical pointers
Altitude can sneak up on visitors, so hydrate well. The market’s heated tents are warm enough for long, relaxing evenings.
5. San Francisco – Coastal Christmas on the West Coast
What makes San Francisco spectacular in December is its ability to blend cozy winter markets with oceanfront scenery. Union Square shines under a massive Christmas tree, the Ferry Building hosts high-end craft bazaars, and Ghirardelli Square becomes a chocolate lover’s paradise.
It’s a dream dual-city match for December travelers — especially with flights from California opening the gateway to West Coast explorations and flights from New York helping visitors pair a New York winter with a San Francisco coastal holiday.
Practical pointers
Pack layers — San Francisco’s weather shifts rapidly. Ride the cable cars after dark for incredible city-light views.
6. Orlando – Christmas in Sunshine and Palm Trees
Orlando proves that snow is optional for Christmas magic. Disney Springs hosts nightly holiday markets, Universal Studios launches themed pop-ups, and local craft festivals radiate holiday energy among palm trees and warm breezes.
Orlando is a perfect stop for travelers building multi-city warm-weather itineraries using flights from Florida, or as a sunny follow-up to snowy northern destinations reached via flights from New York.
Practical pointers
Bring walking shoes — parks and markets cover lots of ground. Expect warm days and mild nights, perfect for outdoor holiday events.
Mistakes to Avoid During Holiday Travel
Even experienced travelers fall into common traps during December trips. Avoiding the pitfalls below saves time, money, and sanity:
| Mistake | What Happens | What to Do Instead |
| Booking too late | Prices surge, hotels sell out | Secure travel early — especially peak flights like flights from New York |
| Ignoring weather | Packing fails, plans disrupted | Check temps across each city — Chicago ≠ Orlando |
| Overpacking | No room for gifts | Pack light and leave “shopping space” |
| Underestimating crowds | Lost hours in queues | Visit markets early or on weekdays |
| Not planning intra-city travel | Missed events and stress | Pre-map transit options, rideshare, and walking distances |
Bonus: Insider Tips to “Make It Grand”
When to Go
The sweetest holiday window is December 8–22 — peak Seasonal charm without Christmas Eve crowds.
Weather Expectations
• Northeast & Midwest — below freezing, heavy snow possible
• West Coast — mild days, cool nights
• Southeast — warm and sunny with crisp evenings
Sustainability Tip
Markets love reusable tote bags — bring one and support plastic-free shopping.
Door-to-Door Journey Tip
Fly into one city and home from another to maximize festive experiences — multi-city tickets make it easy.
Make Your Festive Journey Effortless
Whether you’re beginning your adventure under the dazzling lights of Bryant Park, raising a glühwein mug in Chicago, sipping cocoa in San Francisco, breathing mountain air in Denver, or celebrating Christmas beside palm trees in Orlando — your holiday itinerary should feel magical from departure to return.
Door2Door Flights makes that seamless. You can mix snowy cities with sunny escapes, book multi-city routes with flights from New York, cross-country combinations powered by flights from California, and coastal or southern Christmas finales via flights from Florida — all in one smooth, curated journey.
From home pickup to holiday lights,
we’ll get you there Door to Door — joyfully, effortlessly, and on time for Christmas.
