Chicagoland Bookstore Holiday Trolley

Holiday Bookstore Trolley

Climb aboard a holiday trolley for a festive ride, stopping at indie bookstores along your route! Our first ever Chicagoland Holiday Bookstore Trolley brings together 43 indie bookstores across the city and suburbs for an extra special holiday shopping experience. Get your favorite holiday sweater ready!

Event Highlights:

• Trolley Ride: Travel to 4-5 participating independent bookstores on a fun and festive trolley. Each trolley will have a unique host aboard to guide the experience.
• Holiday Swag: Each ticket includes Chicagoland Holiday Bookstore Trolley swag. Details to come 😎
• Holiday Shopping: Spend time in each bookstore browsing shelves of handpicked reads, unique gifts, and seasonal surprises.

There are 10 different routes to choose from, and each route includes stops at 4-5 bookstores. Each route has a unique starting location (in Chicago and Surrounding Suburbs) and a unique duration. Please review the schedule options carefully to make sure you select the correct tickets. Route details are listed below!

AND! When you purchase your trolley ticket before November 15, 2025 at 11:59 pm, you’ll be entered into a raffle where two lucky winners will receive a 2-ticket package to see A Christmas Carol at Goodman's Albert Theatre!

This is our first year launching this program, and we can’t wait for you to join us! As always, thank you for shopping local and supporting independent bookstores.

Route 1 - Saturday Morning 12/06 - 9:30 AM

Tour begins and ends at Bookends & Beginnings, 1620 Orrington Ave, Evanston, IL 60201

Stops on Route 1:

Bookends & Beginnings (start)

Book Bin

New Book Joy - Chicago

Zora's Place

Booked

Bookends & Beginnings (end)

Route 2 - Saturday Afternoon 12/06 - 2:00 PM

Tour begins and ends at Restoried Bookshop, 4613 N Kedzie Ave, Chicago, IL 60625

Stops on Route 2:

Restoried Bookshop (start)

Time and a half Books

Women & Children First

Three Avenues Bookshop

Restoried Bookshop (end)

Route 2b - Saturday Afternoon 12/06 - 3:00 PM

Tour begins and ends at Restoried Bookshop, 4613 N Kedzie Ave, Chicago, IL 60625

Stops on Route 2b:

Restoried Bookshop (start)

Time and a half Books

Women & Children First

Three Avenues Bookshop

Restoried Bookshop (end)

Route 3 - Sunday Morning 12/07 - 10:30 AM

Tour begins and ends at The Book Stall, 811 Elm St, Winnetka, IL 60093

Stops on Route 3:

The Book Stall (start)

About Time Bookstore

Lake Forest Book Store

Secret World Books

The Book Stall (end)

Route 4 - Sunday Afternoon 12/07 - 2:00 PM

Tour begins and ends at Los Amigos Books, 2207 N Western Ave C2, Chicago, IL 60647

Stops on Route 4:

Los Amigos Books (start)

Perpetual Books

Madison Street Books

Volumes Bookcafe

Los Amigos Books (end)

Route 4b - Sunday Afternoon 12/07 - 3:00 PM

Tour begins and ends at Los Amigos Books, 2207 N Western Ave C2, Chicago, IL 60647

Stops on Route 4b:

Los Amigos Books (start)

Perpetual Books

Madison Street Books

Volumes Bookcafe

Los Amigos Books (end)

Route 5 - Saturday Morning 12/13 - 9:30 AM

Tour begins and ends at Da Book Joint, 6900 S Stony Island Ave, Chicago, IL 60649

Stops on Route 5:

Da Book Joint (start)

Love's Sweet Arrow

Seminary Co-op

Call & Response Books

57th Street Books

Da Book Joint (end)

Route 5b - Saturday Morning 12/13 - 10:30 AM

Tour begins and ends at Da Book Joint, 6900 S Stony Island Ave, Chicago, IL 60649

Stops on Route 5b:

Da Book Joint (start)

Seminary Co-op

Call & Response Books

57th Street Books

Da Book Joint (end)

Route 6 - Saturday Afternoon 12/13 - 2:00 PM

Tour begins and ends at The Book Loft, 1047 Lake St, Oak Park, IL 60301

Stops on Route 6:

The Book Loft Oak Park (start)

The Pile Bookstore

New Book Joy - Brookfield

Dandelion Bookshop

The Book Loft Oak Park (end)

Route 7 - Sunday Morning 12/14 - 9:30 AM

Tour begins and ends at Bucket O' Blood 3182 N Elston Ave, Chicago, IL 60618

Stops on Route 7:

Bucket O'Blood Books & Records (start)

Uncharted Books

The Last Chapter Book Shop

Goblin Market

Lilliput Books

Bucket O'Blood Books & Records (end)

Route 7b - Sunday Morning 12/14 - 10:30 AM

Tour begins and ends at Bucket O' Blood 3182 N Elston Ave, Chicago, IL 60618

Stops on Route 7b:

Bucket O'Blood Books & Records (start)

Uncharted Books

The Last Chapter Book Shop

Goblin Market

Lilliput Books

Bucket O'Blood Books & Records (end)

Route 8 - Sunday Afternoon 12/14 - 2:00 PM

Tour begins and ends at Skunk Cabbage Books, 2826 N Milwaukee Ave, Chicago, IL 60618

Stops on Route 8:

Skunk Cabbage Books (start)

The Understudy Coffee and Books

Slant of Light Books

City Lit Books

Skunk Cabbage Books (end)

Route 8b - Sunday Afternoon 12/14 - 3:00 PM

Tour begins and ends at Skunk Cabbage Books, 2826 N Milwaukee Ave, Chicago, IL 60618

Stops on Route 8b:

Skunk Cabbage Books (start)

The Understudy Coffee and Books

Slant of Light Books

City Lit Books

Skunk Cabbage Books (end)

Route 9 - Saturday Morning 12/20 - 9:30 AM

Tour begins and ends at The Bookstore of Glen Ellyn 475 N Main St, Glen Ellyn, IL 60137

Stops on Route 9:

The Bookstore of Glen Ellyn (start)

Town House Books & Café

Harvey's Tales Bookstore

Yellow Bird Books

The Bookstore of Glen Ellyn (end)

Route 10 - Saturday Afternoon 12/20 - 2:00 PM

Tour begins and ends at Newberry Bookshop, 60 W Walton St, Chicago, IL 60610

Stops on Route 10:

Newberry Bookshop (start)

Pilsen Community Books

Sandmeyer's Bookstore

Passages Wine and Books

Newberry Bookshop (end)