1. Sat, Nov 22, 2025

   Wintrust Magnificent Mile Lights Festival

   Parade ~5:30 PM • Fireworks ~7:15–7:30 PM North Michigan Ave / River North

   Chicago’s holiday kickoff: daytime activities, evening tree-lighting parade, and fireworks over the river.

   • Best view: Upper Wacker by the Wrigley Building (arrive 60–90 minutes early).
   • Closures: Expect rolling barricades; plan drop-off north of the river and walk in.
   • Duration: 2–3 hrs if watching parade + fireworks.

   Family-friendlyFreeOutdoors

   Official site

2. Nov 20–Dec 24, 2025

   Christkindlmarket (Daley Plaza)

   50 W Washington St (Loop) • Free entry Weeknights = lighter crowds

   German-style stalls, glühwein mugs, ornaments, and snacks in the heart of the Loop.

   • Drop-off: Clark & Washington is efficient for groups.
   • Timing: Go Mon–Thu after 5 PM for the lights without weekend lines.
   • Duration: 60–90 minutes for a full lap + photos.

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3. Nov 21, 2025 – Jan 4, 2026

   ZooLights at Lincoln Park Zoo

   Lincoln Park • Evenings ~4:30–9 PM Closed Thanksgiving Day

   Light tunnels, animated displays, music-synced trees—holiday photo gold.

   • Tickets: Reserve for prime Fridays/Saturdays.
   • Group flow: Use Cannon Dr. for fastest drop/pick-ups.
   • Duration: 75–120 minutes at an easy pace.

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   Official site

4. Thu, Nov 27, 2025 • 8–11 AM

   Chicago Thanksgiving Parade (State Street)

   Arrive by ~7:00 AM for curb views Route: Ida B. Wells → Randolph

   Marching bands, balloons, floats—classic State Street energy.

   • Grandstands: Buy early; they sell out.
   • Comfort move: Stage a warm vehicle nearby for post-parade pickup.
   • Duration: 2.5–3 hours including arrival buffer.

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5. Opens Fri, Nov 14, 2025

   Maggie Daley Park Ice Skating Ribbon

   337 E Randolph St (Loop) • Rentals available Reservations recommended (evenings/weekends)

   Quarter-mile ribbon with gentle hills and skyline views—great for first-timers and date nights.

   • Book: Evening and weekend slots sell out quickly.
   • Add-on: Photos at Cloud Gate (“The Bean”) 5–8 minutes away.
   • Duration: 60–90 minutes including rentals.

   SkatingOutdoorsReservations

   Official site

Dates reflect the 2025 season. Always confirm hours, tickets, and weather advisories before heading out.