Travel Like a Local: Chicago, Illinois

There is something about boarding a plane and knowing you will land in a city much bigger than the one you are leaving. Chicago has that big city, towering buildings, iron skillet of people from all walks of life that has always intrigued me.

From the famous hot dogs to fine dining, hidden bars to late night rooftops, plus a cultural explosion of art and history and theatre, there’s a trip to Chicago that will fit almost every budget and personality type. This city has it all. And since I’m going to be insisting you go see my new favorite play, Southern Gothic, I wanted to be sure we give you some ideas for how to have the most epic weekend escape to the Windy City.

Here is a quick guide to navigating Chicago on a dime or going BIG! Tag Good Grit in your pictures on your next trip!

Explore 

• Garfield Park Conservatory

• The Field Museum

• The Art Institute of Chicago

• Chicago Cultural Center

• Richard H. Driehaus Museum

• Lincoln Park Zoo

• The Second City

• Windy City Playhouse

Eat & Drink

• Sawada Coffee

• The Crepe Shop

• Doughnut Vault

• Parson’s Chicken & Fish

• Oasis Cafe

• Superdawg Drive-In

• Avec

• Lou Malnati’s

• 3 Arts Club Cafe

• Three Dots and a Dash

• Garrett Popcorn

Stay

• Chicago Athletic Association

• Freehand Chicago

• The Robey

• ACME Hotel Company Chicago

• Hotel Thompson

• Talbott Hotel

• Longman & Eagle

• Airbnb (various locations)