31. Dive into History at Newberry Library
What is it?
An independent research library founded in 1887.
Why go?
From medieval manuscripts to rare maps and literary archives, the Newberry’s exhibitions and lectures are free and open to the public.
Don’t miss:
Free guided tours of rotating exhibitions.
32. Crate Dig at Dusty Groove
What is it?
A beloved Wicker Park record store.
Why go?
Browse expertly curated vinyl spanning Tropicalia, Afrobeat, reggae, jazz, soul and more. Music lovers can easily lose hours here.
Don’t miss:
Hard-to-find international pressings and obscure reissues.
33. Feel the Thrill at 360 CHICAGO
What is it?
An observation deck atop the former John Hancock Center.
Why go?
From 1,030 feet above the Magnificent Mile, the views stretch across Lake Michigan and beyond. Enjoy cocktails while soaking it all in.
Don’t miss:
TILT—a glass platform that slowly tips you 30 degrees over the edge of the building.
34. Wander Through Chinatown
What is it?
One of the city’s cultural hubs, filled with restaurants, shops and East Asian architecture.
Why go?
Stroll through Chinatown Square, explore Wentworth Avenue and admire skyline views from Ping Tom Memorial Park.
Don’t miss:
Dumplings, Peking duck, bubble tea and inventive cocktails—come hungry.
35. Relax in Chicago’s Gardens
What is it?
The city’s serene parks, conservatories and botanical gardens.
Why go?
Reconnect with nature among Japanese gardens, lily ponds and rose collections—many free to visit.
Don’t miss:
Seek out Chicago’s lesser-known “secret” gardens tucked into quiet neighborhoods.
36. Browse at Pilsen Community Books
What is it?
A worker-owned bookstore in Pilsen.
Why go?
Support a local business while discovering new and used titles. Staff recommendations are thoughtful and personal.
Don’t miss:
Add a donation to Liberation Library to help provide books for incarcerated youth.
