Hey there,
Thinking about a winter escape but not sure where to start? Between Chicago’s Christmas tunnel of lights and parade dates, Colorado’s kid-ski-free perks and wild terrain, and Montreal’s Thanksgiving mix of markets, bagels, and Black Friday deals, this edition lines up trips you can actually put on the calendar.
Settle in and let these ready-made routes turn your next long weekend into something you will actually look forward to.
📰 Upcoming in this issue
🎄 Chicago Christmas, Booked: 10 Classics to Lock In Now
🎿12 Colorado Ski Resorts With Big Perks: Kids Ski Free, $11 Lifts, 29K Acres
🍁 Montreal for Thanksgiving: Big Flavors, Better Prices, Easy Wins
📈 Trending news
🎄 Chicago Christmas, Booked: 10 Classics to Lock In Now
Time Out’s Chicago list rounds up can’t-miss holiday staples with exact dates, routes, and rink rules. Families and visitors can plan weekends around market openings, parade times, and sell-out light shows. The unlock is clarity, from Christkindlmarket’s run to Botanic Garden tunnel stats so that you can reserve, ride, and skate without stress.
Key Takeaways:
🗓️ Dates you Need: Christkindlmarket runs Nov. 21–Dec. 24. The City Tree shines Nov. 21–Jan. 8. Lights Fest parade pops Nov. 22 at 5:30 pm.
✨ Lights with Wow: Lightscape’s 110-foot tunnel packs 100,000 bulbs, through Jan. 4. ZooLights floods Lincoln Park Zoo with millions of LEDs.
🚆 Ride the Cheer: CTA Holiday Train rolls Nov. 28–Dec. 22, with Santa on the exterior. Metra adds themed rides Dec. 6, 13, 20.
⛸️ Skate Smart: Millennium Park rink offers free weekend lessons, reservations required. Maggie Daley’s Ribbon books up fast, runs into March.
🎿 12 Colorado Ski Resorts with Big Perks: Kids Ski Free, $11 Lifts, 29K Acres
Travel + Leisure ranks a dozen Colorado mountains for families, powder hounds, and après lovers, highlighting concrete wins like $11 lift tickets, kids-ski-free weeks, and four-mile runs. The unlock is perk stacking, from train-to-slope access to heli terrain so that you can match budget, skill, and vibe without guesswork.
🧒 Family Value: Keystone offers kids under 12 a free ski day with a stay, while Purgatory starts lift tickets at $11 and offers free Power Kids passes.
🏔️ Massive Terrain: Vail packs 5,300 skiable acres and a four-mile run, while Silverton adds heli drops across 29,000 wild acres.
🚆 Easy Arrival: Skip I-70 traffic, ride Denver’s Union Station Winter Park Express straight to the lifts, then book pro tune-ups on arrival.
🍷 Après Standouts: Telluride’s Allred’s and Alpino Vino headline dining with summit views, while Aspen Snowmass layers four mountains and luxe village culture.
🍁 Montreal for Thanksgiving: Big Flavors, Better Prices, Easy Wins
Montreal sells Thanksgiving as a quick, high-reward getaway for food lovers and deal hunters. Visitors eat through markets and classic spots, then stack savings with a strong USD and citywide Black Friday sales. The hook is compact and fun, since most highlights are within walking distance or a short metro ride, so plans stay simple.
💵 Currency Boost: Strong USD stretches in Montreal, trimming hotel, dining, and shopping bills without cutting experiences or neighborhoods.
🥯 Iconic Bites: Hit Jean-Talon and Atwater markets, St-Viateur bagels, and Schwartz’s smoked meat for fast, flavorful wins.
🛍️ Black Friday Haul: Work Sainte-Catherine’s stores and the Eaton Centre, then refuel at Time Out Market with local favorites.
🚇 Compact Moves: Walk Old Montreal, ride the metro to Mile End and Plateau, and keep transfers short from YUL to downtown.
🔔 Mark Your Calendar
1. 🥁 50th Annual Winternational Thanksgiving Day Parade
A Golden Jubilee Thanksgiving-morning tradition in North Miami with marching bands, floats, and hometown pride.
Event Details:
📅 Date: Thursday, November 27, 2025, 10 am–12 pm.
📍 Location/Route: Downtown North Miami, along NE 125th Street from NE 6th Ave to NE 10th Ave; main stage at North Miami City Hall, 776 NE 125th St, North Miami, FL 33161.
🎟️ Tickets/Admission: Free community parade, open to the public.
🎉 Highlights: Marching bands and drumlines, themed floats, cultural performances, mascots, and classic cars, with a family-friendly Thanksgiving kickoff.
🔗 More info: 50th Annual WinterNational Thanksgiving Day Parade
2. 🎈 Macy’s Thanksgiving Day Parade 2025
Celebrate a nearly 100-year holiday tradition in New York City with giant balloons, floats, bands, and more.
Event Details:
📅 Date: Thursday, November 27, 2025.
⏰ Start Time: Approximately 8:30 a.m. ET (runs until around noon).
📍 Location/Route: Manhattan, NY -- 2.5-mile public viewing route ending at Macy’s Herald Square.
🎟️ Admission: Free for spectators along the public route; TV broadcast on NBC and streaming via Peacock.
🎉 Highlights: Iconic giant character balloons, 20+ floats, marching bands, live performances, and kickoff of the holiday season.
🚫 Note: Very large crowds and early arrival are recommended for street viewing; weather may affect balloon flight.
🔗 More info: Macy’s Parade Official Site
📊 Take This Edition’s Poll:
Which trip feels like the smartest spend for a great experience 🧭
Why It Matters
Trips get stressful when you are piecing together dates, prices, and must-see spots from random tabs and half-finished notes. Clear picks with specific perks, timing, and transit options make it much easier to match your budget and energy to the right destination.
Use this rundown to swap guesswork for plans that feel simple, fun, and doable.
Until next time, Bon voyage!
Zoe Reed
Editor-in-Chief
Passport to Paradise
P.S. Interested in sponsoring a future issue? Just reply to this email and I’ll send packages!
