• Chicago
  • 1
  • Days
  • Activities
About this trip

Here’s some of Chicago’s hidden gems for everything thrilling, strange, and all in between. Start the day in the 80s by treating yourself to breakfast at The Wormhole Coffee. Movie buffs would be remiss to miss the Untouchables Tour, which showcases Chicago’s favorite criminals ruling the 20s.

Recommended accomodation
Sofitel Chicago Magnificent Mile

www.sofitel-chicago.com

20 E Chestnut St, Chicago, IL 60611

  • Day Plan
  • Map

1 Hour

The Wormhole Coffee

See the DeLorean as you're transported back to the '80s for a cup of coffee. Pair it with one of their in-house made baked goods.

1462 N Milwaukee Ave, Chicago, IL 60622

See Website

Wormhole Coffee Chicago

See the DeLorean as you’re transported back to the ’80s for a cup of coffee. Pair it with one of their in-house made baked goods.

 

1462 N Milwaukee Ave, Chicago, IL 60622

  • Wormhole Coffee Chicago
  • Wormhole Coffee Chicago
  • Wormhole Coffee Chicago
  • Wormhole Coffee Chicago

2 Hour

Untouchable Tour

If old gangster films are your go-to, this unique tour is for you. Learn about the local legends that ruled the streets in the 1920s.

600 N Clark St, Chicago, IL 60654

See Website

Untouchable Tour Chicago

If old gangster films are your go-to, this unique tour is for you. Learn about the local legends that ruled the streets in the 1920s.

 

600 N Clark St, Chicago, IL 60654

  • Untouchable Tour Chicago
  • Untouchable Tour Chicago
  • Untouchable Tour Chicago
  • Untouchable Tour Chicago

1 Hour

iFLY Chicago Lincoln Park

Want to skydive, but are afraid of heights? Lincoln Park has their very own wind tunnels. Also has gravity-centric learning opportunities.

800 W Scott St, Chicago, IL 60610

See Website

ifly Lincoln Park Chicago

Want to skydive, but are afraid of heights? Lincoln Park has their very own wind tunnels. Also has gravity-centric learning opportunities.

 

800 W Scott St, Chicago, IL 60610

  • ifly Lincoln Park Chicago
  • ifly Lincoln Park Chicago
  • ifly Lincoln Park Chicago
  • ifly Lincoln Park Chicago

0.75 Hour

Woolly Mammoth Antiques & Oddities

An oddities store that has a bit of everything. Great gifts for that curious special someone - bones, books & more!

1513 W Foster Ave, Chicago, IL 60640

See Website

Woolly Mammoth Chicago

An oddities store that has a bit of everything. Great gifts for that curious special someone – bones, books & more!

 

1513 W Foster Ave, Chicago, IL 60640

  • Woolly Mammoth Chicago
  • Woolly Mammoth Chicago
  • Woolly Mammoth Chicago
  • Woolly Mammoth Chicago

0.75 Hour

Superdawg Drive In

A place for the community searching out comfort food. They've been serving drive-in style since 1948 and have only gotten better with age.

6363 N Milwaukee Ave, Chicago, IL 60646

See Website

Superdawg Chicago

A place for the community searching out comfort food. They’ve been serving drive-in style since 1948 and have only gotten better with age.

 

6363 N Milwaukee Ave, Chicago, IL 60646

  • Superdawg Chicago
  • Superdawg Chicago
  • Superdawg Chicago
  • Superdawg Chicago

1.5 Hour

Kit Kat Lounge

Have a break, and visit the Kit Kat Lounge. They pride themselves on being a safe space for all kinds of entertainers and patrons.

3700 N Halsted St, Chicago, IL 60613

See Website

Kit Kat Lounge Chicago

Have a break, and visit the Kit Kat Lounge. They pride themselves on being a safe space for all kinds of entertainers and patrons.

 

3700 N Halsted St, Chicago, IL 60613

  • Kit Kat Lounge Chicago
  • Kit Kat Lounge Chicago
  • Kit Kat Lounge Chicago
  • Kit Kat Lounge Chicago