Chicago Guide

Posted by Chris Ibbitson on Mon, Dec 22, 2025

I’ve been to Chicago a couple of times on holiday. Not massively explore the place, but the following is a list of places I’d recommend checking out!

Bars

  • Barstool fun sports bar with a tonne of games to play (think shuffle board etc).
  • Purple Pig Restaurant have not eaten here, but have had a few drinks here before. Good wine list, and nice cocktails. Great atmosphere!
  • Larry’s at the Lawrence House nice cocktail bar tucked inside a apartment building.
  • Pops for Champagne nice little Champagne bar. Cool place.
  • Scofflaw nice little neighbourhood bar. Great gin martini, and if you are peckish the Scofflaw Burger is pretty good!!
  • Lush Wine and Spirits great little neighbourhood wine bar which also does nice cheese and charcuterie, along with bigger plate options too.

Brewery and Brew Pubs

Food

  • Giordano’s recommended by a friend who lives in the US, great place to get deep dish pizza!
  • Chicago Chop House great steakhouse. The whipped mashed potatoes covered in Padano are amazing!
  • Time Out Market cool place in Fulton Market to grab a bite to eat from the many vendors, or just a drink.
  • Sun Wah BBQ hong kong style BBQ restaurant. The duck is amazing!
  • Rojo Gusano taco restaurant, mexican eats and great cocktails.

Things to do