Holidays in Andersonville
holiday_markets_and_shopping

Artistic rendering โ€“ Event may differ

Holidays in Andersonville

Festive Holiday Trolley with Santa visits and local business stops.

About

Experience the festive spirit of Andersonville during the holidays! This vibrant neighborhood offers a charming escape with unique shopping, delightful dining, and special events. Ride the festive Holiday Trolley, meet Santa, and discover local treasures. From delicious Thanksgiving feasts to sweet cookie decorating, there's holiday magic for everyone.

Our Take

Family Friendly

๐ŸŽ„ ๐ŸŽ„ ๐ŸŽ„ ๐ŸŽ„ ๐ŸŽ„ (5/5)

Best For

Families, couples, shoppers

Vibe

Festive, community-oriented, charming

Energy Level

Moderate

Budget

$$

Photo Friendly

๐Ÿ“ท ๐Ÿ“ท ๐Ÿ“ท ๐Ÿ“ท ๐Ÿ“ท (4/5)

Weather Sensitivity

Moderate

Special Events & Promotions

  • Download the Andersonville Holiday Brochure and 2024 Shop Local Passport.
  • First 40 kids on the trolley Saturday get a FREE scoop card from Jeni's Ice Cream.
  • Santa will be on board the Holiday Trolley on Saturday.
  • Stewpendous Productions hosts Trolley Trivia on Sunday.
  • Many restaurants offer Thanksgiving dinner to-go and dine-in options.

Tags

holiday marketfamily friendlySanta visitsfestive foodholiday shoppingcommunity celebrationseasonal activitiesholiday traditionlocal businesses

Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.

Location

1554 W Hollywood Ave
Chicago, IL

Event Details

Pricing

$$

Duration

Varies by event

Ages

All ages

Neighborhood

Andersonville

Timed Entry

No

Organizer

Andersonville Chamber of Commerce

Practical Information

Pet Policy

No pets allowed (service animals welcome) for most events, check specific event details.

Food & Drink

Full dining options available, including Thanksgiving specials and festive treats.

Tips & Advice

  • Check the Holiday Trolley schedule and route in advance to plan your stops and maximize your exploration of Andersonville's shops and eateries.
  • Arrive early for the Holiday Trolley on Saturday to be among the first 40 kids to receive a free scoop card from Jeni's Ice Cream.
  • Consider downloading the 2024 Shop Local Passport to discover special offers and support local businesses throughout your visit.
  • Many restaurants offer Thanksgiving pre-orders; book well in advance to secure your holiday meal from local favorites like Bar Roma or Big Jones.
  • Look for 'Late Night Andersonville' events for extended shopping hours, offering a more relaxed browsing experience.

Frequently Asked Questions

What are the dates for the Holiday Trolley?

The Holiday Trolley runs on Saturday, December 7, and Sunday, December 8, from 11 AM to 4 PM.

Can I bring my pet on the Holiday Trolley?

Generally, pets are not allowed on the trolley, though service animals are welcome. It's best to confirm specific policies.

Where does the Holiday Trolley route stop?

The trolley makes stops at various points including The Guesthouse, BarRoma, Swedish American Museum, Dearborn Denim, and several street corners along Clark Street.

Are there any special activities with Santa?

Yes, Santa will be on board the Holiday Trolley on Saturday from 12:30 PM to 3:30 PM for photos and wishes, and there's a Cookie Decorating with Santa event.

Where can I find holiday dining options?

Andersonville features numerous restaurants offering holiday specials, including Thanksgiving dinners to-go and dine-in options. Check the 'Holiday Dining in Andersonville' section for details.

Nearby Places (10 total)

Contributors & Updates

Last Updated: Oct 23, 2025
Original Submitter: Sep 17, 2025 The ChristmasLocal.com editorial team

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