Chicago City Guide

Chicago City Guide

Chicago is one of the country’s best cities for all things food, culture, art, sports, etc. It’s a place you can spend years in and never get bored. We’ve done the legwork for you and have some great tips and recommendations for your trip to the Windy City.  


  • Take the El! The El (elevated train) is a cheap and easy way to get around the city.
  • Pack accordingly – summers are hot and humid, winters are frigid and snowy. Chicago is a city with four distinct seasons.
  • Don’t hesitate to ask a local for help or advice. Chicagoans are quite friendly.
  • Soda is called “pop.”
  • Take advantage of the 198 neighborhoods in Chicago, just be careful heading into some of them.
  • If you’re driving, be careful of getting stuck in a notorious Chicago traffic jam. They can last hours. Avoid airport routes and rush hour, if you can.
  • Develop a dining game plan. Chicago has lots of food and most of it is heavy. Pace yourself.
  • Take the Riverside Walk, especially the area between Michigan Avenue and the lake front.


Chicagoans love their food, especially the dishes they’ve invented, and there’s a bunch of them. Here’s our picks for the best places to get everything that makes Chicago’s food scene special.
Deep Dish Pizza – Bartoli’s Pizzeria – Roscoe Village

*also check out Pequod’s Pizza and The Art of the Pizza for Chicago deep dish

 Chicago-style Hot Dog – Jimmy’s Red Hots – Humboldt Park

 Italian Beef Sandwich – Al’s #1 Italian Beef – University Village

*Also check out Johnnie’s Beef for old-school Italian beef sandwiches

Jibarito – Papa’s Cache Sabroso – Humboldt Park

Mother-in-law – Fat Johnnie’s – South Side

 Francheezie – The Bagel – Lake View

 Chicken Vesuvio – Il Vicinato – Heart of Italy

 Maxwell Street Polish – Jim’s Original – University Village

A few of our other favorites include:


Insider’s Pick – Catch a day game at Wrigley

The Cubs were the last team in Major League Baseball to receive lights for night games, and to this day they play more day games than any other team. There is something special about coming here for a day game, singing “Take Me Out to the Ballgame”, and having some Cracker-Jacks.

No matter what you’re into, Chicago can make it happen. It’s a true American City with a can-do attitude. It has a blue-collar spirit and a wealth of unique cultural experiences. We hope your visit is memorable, and be sure sure to check out and plan your trip!