Sales Travel Guide - Chicago

If you travel for sales, chances are you will wind up in Chicago at some point. Whether it’s a layover at O'Hara, one of the largest international airports in the world, or to visit one or the many large corporations housed here, you will find Chicago as a hospitable, yet hectic city. Many of the largest insurance, publishing, and manufacturing companies in the world are either headquartered or have a location in Chicago. In addition, Chicago has a very healthy venture capital and start up environment, which has given birth to some very successful companies over the past 10 years. Here’s our guide to navigating and making the most out of your trip.


There are two major airports in Chicago; O'Hara and Midway. If you are flying Southwest, odds are you will take Midway. Otherwise, you’ll find your way to O'Hara. I’ll focus on O'Hara. The airport itself has a number of wonderful dining options. If you are flying United you will find yourself in the main terminal. Other airlines such as American are split off. The airport is massive so it isn’t easy to explore dining options in different terminals. Here are some good recommendations by terminal:



Getting to the city

If taking an uber, head to the Rideshare lot on the upper level above baggage claim. Uber pool is a good option. It costs about half and most of the time nobody else will try to carpool with you.

The subway is a cheaper, but longer option. Chicago Transit Authority (CTA) runs a solid operation.

Food while in town

There are a number of restaurants in the Harry Caray group that capture the spirit of the late-great broadcaster. Many of them have great happy hours and even better food.

As covered in our New York edition, Eataly is a great destination for a variety of Italian food, groceries, and beer from all over.

It wouldn’t be Chicago without some Chicago style pizza. Giordano’s, Lou Malnati’s, and the original Pizzeria Uno can fight over the title of best Chicago style pizza. It’s more fun for the rest of us to try them all.

Entertainment while in town

If you are in town visiting clients, a Chicago Cubs game is a great, fairly inexpensive way to break the ice. If you want to spend more or host numerous clients, look into the rooftop apartments across the street from Wrigley Field.


The Bean - Officially titled “Cloud Gate,” this sculpture in the middle of the Loop Community has to be seen in person.

You can also get a great view of the city in the Chicago Skydeck at the Willis (formerly Sears) Tower or the 360 Observatory at the John Hancock Center.